Personalized care for your dog or cat - Near South Side

Highly-rated overnight sitters - Near South Side

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ksenia D.
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Ksenia D.
Star Sitter
from
$50
per night
4.9 out of 5 stars
46 reviews
21 repeat clients
4 years of experience
Near North Side, Chicago, IL, 60611

Ksenia did a wonderful job taking care of my pup Wilbur! She made sure he had plenty of fun and enrichment and gave me plenty of updates during his one week stay. Her pup Stella is so so sweet, and her and Wilbur were best friends. I can't recommend her enough!

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Maddie E.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
206 reviews
73 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley is amazing and was able to take my girls on short notice! They love spending time with Ashley and her daughter Marina and I know they are super well cared for! 🐾💜

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Angie S.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
149 reviews
6 repeat clients
3 years of experience
Near South Side, Chicago, IL, 60605

Ania was great! Very professional, kind and reliable sitter. Simba had a wonderful stay with Ania! Lots of photo/video updates, I can see my dog was truly well taken care of! Will definitely book with her again in a future 💕

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Arina U.
Sitter Profile Image: Jenna M.
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Jenna M.
Star Sitter
from
$53
per night
5.0 out of 5 stars
102 reviews
24 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

She was an amazing choice and Bailey loved being with her and her doggo. If you want a safe sitter and one that will give all their love and attention to them, she is the one! I will most definitely be rebooking again.

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Richard G.
Sitter Profile Image: Ann V.
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Ann V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
141 reviews
30 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60605

Ann takes such good care of my dog and truly treats him like her own! She’s very flexible and gives great updates, really appreciate her good communication!

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Denise R.
Sitter Profile Image: Andrea B.
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Andrea B.
Star Sitter
from
$57
per night
5.0 out of 5 stars
18 reviews
3 repeat clients
15 years of experience
Loop, Chicago, IL, 60607

Andrea was consistently communicative throughout my dog’s stay - I felt comfortable going out of town because she kept my dog safe and happy! Not only did Andrea accept my last minute boarding request but she made sure to clarify any questions to ensure that my dog was well taken care of. I would book her again!

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Anne N.
Sitter Profile Image: Andre S.
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Andre S.
from
$57
per night
4.8 out of 5 stars
20 reviews
5 repeat clients
8 years of experience
Loop, Chicago, IL, 60605

Andre took amazing care of Howie during his stay!! Andre and his partner sent me updates and made me feel at ease while I was away! I will definitely recommend Andre to anyone!!

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Nadia S.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.9 out of 5 stars
29 reviews
8 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Timothy was a wonderful sitter ! He shared updates and photos regularly and gave my dog extra food because I didn’t pack enough. He was also very gracious to let me extend my booking on short notice due to travel delays. Highly recommend Timothy and hope we can book with him again !

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Michelle C.
Sitter Profile Image: Fatima P.
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Fatima P.
from
$55
per night
5.0 out of 5 stars
7 reviews
7 years of experience
Near North Side, Chicago, IL, 60610

Fatima was very communicative and sent lots of photos which we loved! We didn’t worry about our pup at all which was very nice. Will def book with her again!

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Jasmine D.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
31 reviews
12 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

Daphnay was wonderful. I was really scared to leave my baby with a stranger and Daphnay put me at ease. I highly recommend her and will be using her again in the future.

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L M P.
Sitter Profile Image: Hoon kee K.
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Hoon kee K.
Star Sitter
from
$52
per night
5.0 out of 5 stars
16 reviews
5 repeat clients
10 years of experience
Loop, Chicago, IL, 60601

Hoon was great with Eva, took great care of her, sent lots of photos and updates on time, and was super communicative. I'd totally recommend him, no problems at all.

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SanziL M.
Sitter Profile Image: Ann-Marie H.
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Ann-Marie H.
Star Sitter
from
$55
per night
5.0 out of 5 stars
27 reviews
11 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Ann-Marie took great care of my fur baby while I was out of town. She sent pictures throughout the stay, maintained communication, and was flexible when we pushed our return to a later time. I would definitely recommend her and look forward to hiring her again in the future.

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Era L.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
392 reviews
185 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Teddy is our 150lb Bullmastiff and EK and her family welcomed him like the rest of the tiny tots that are looked after daily. She is trustworthy and reliable. We hadn't been on a real vacation in 2yrs we had no issues or worries while gone.

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Susan L.
Sitter Profile Image: Patrick & Susan C.
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Patrick & Susan C.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Near South Side, Chicago, IL, 60605

About: I’ve had dogs for over 25 years - from puppyhood through their senior days. My last dog passed away late last year, and now we’re looking forward to taking care of other people’s dogs! My wife and are retired and on the days we accept reservations will have plenty of time to take your dog on long walks and play! We have a single-floor apartment in the South Loop, We can accommodate a crate if your dog uses one. We will always follow your guidance on how much or little your dog prefers to interact with other dogs and people.

Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$58
per night
5.0 out of 5 stars
72 reviews
23 repeat clients
50 years of experience
Near North Side, Chicago, IL, 60611

Steven is great. Sends me daily reports with pics. My flight was delayed and he was extremely flexible in helping me out with an extended stay.

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Amy A.
Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
186 reviews
73 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

I have been going to Bola for quite some time now and she is very accommodating when it comes to my 90 pound Goldendoodle. I truly appreciate her flexibility and support in watching him from time to time as I navigate my first pregnancy,

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Christina E.
Sitter Profile Image: Mia L.
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Mia L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
52 reviews
16 repeat clients
10 years of experience
Near North Side, Chicago, IL, 60611

Outstanding host for our two fur babies! Anytime we find a sitter as caring and keen to detail as Mia was to our dogs, we cling on! She’s reliable and she goes the extra mile to make sure the dogs are comfortable and well taken care of. This was a last minute booking because their other sitter was unavailable, however, we feel so lucky to have found her, she adores our dogs and it shows in the interaction between them through the daily photos. We will definitely be booking her again!

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Jada D.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
32 reviews
24 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

We have a 14 year old dog who’s regular sitter could not commit to our 3 week Australia trip so I was nervous to find someone new for an older dog. Cheyanne is amazing, she has experience with older dogs and special needs, my dog was so happy with her and even found a “boyfriend” during her long stay. I did not hesitate to book her again for another long trip, our baby ran out of food but Cheyanne went to the store to buy her more “fresh pet” and even gave her a bath! Our dog loves being a high rise dog and Cheyanne spoils her just like we do.

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Gina M.
Sitter Profile Image: Samantha M.
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Samantha M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
30 reviews
9 repeat clients
10 years of experience
West Town, Chicago, IL, 60642

Samantha and Rosie were amazing! She sent such cute pictures and was very accommodating. I will definitely book again when I need a sitter :)

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Greta F.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$55
per night
5.0 out of 5 stars
106 reviews
31 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni did an amazing job taking care of our fur babies! She was responsive, asked questions, and kept us updated while we were away on our vacation. It was a first time boarding our pets and Anni did a great job easing any concerns we had. Our pets were at ease with her and felt very at home in her space. Would definitely recommend!

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Alyson P.
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Over 4.1 million
dogs curled up for a sleepover in a sitter's home on Rover1

Cat caregivers near you - Near South Side

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
56 reviews
14 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

Nadine was great! She was patient with my sassy cat and very communicative with me while I was on vacation. Would definitely use Nadine in the future.

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Stephanie D.
Sitter Profile Image: Linh N.
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Linh N.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
17 reviews
3 repeat clients
3 years of experience
Loop, Chicago, IL, 60607

Linh is attentive, responsive, and overall a fantastic cat sitter. She took notes of all the care requirements, followed them perfectly, provided detailed updates with lots of pictures, and tried her best to give my cat attention and play time even though he's shy with strangers. Would highly recommend!

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Yexing S.
Sitter Profile Image: Chunshan Y.
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Chunshan Y.
from
$17
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
5 years of experience
Near South Side, Chicago, IL, 60605

Chunshan is very professional and I will go back to her next time.

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Chao F.
Sitter Profile Image: Gabby E.
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Gabby E.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
66 reviews
20 repeat clients
12 years of experience
Loop, Chicago, IL, 60605

Gabby took great care of our kitties while we were away for a week! She even got my very shy cat (who never comes out for sitters) to say hi to her!

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Emily A.
Sitter Profile Image: Hallie B.
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Hallie B.
from
$18
per visit
5.0 out of 5 stars
70 reviews
27 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

Hallie did a great job caring for my cats! I appreciate the updates and pictures while I was away. It brought me peace of mind to know my cats were in good hands!

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Kathryn M.
Sitter Profile Image: Mariam A.
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Mariam A.
from
$13
per visit
5.0 out of 5 stars
41 reviews
13 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Mariam did a fantastic job watching our cat! She was very communicative and professional; she updated us after every visit and sent lots of pictures. 10/10 would recommend and will be using her services again!!

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Mae J.
Sitter Profile Image: Kaylie L.
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Kaylie L.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
34 years of experience
Near South Side, Chicago, IL, 60616

Kaylie made leaving my cats alone for a work trip worry free and I feel a bit guilty that she played with them more than I usually do! She's prompt and reliable and professional.

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Alex H.
Sitter Profile Image: Kate W.
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Kate W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
126 reviews
39 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

Kate was absolutely amazing with my cat, Milo! She sent videos and pictures throughout my time away and made sure to keep me thoroughly updated. She loved him like her own and I am so grateful! Would absolutely recommend Kate to anyone looking for a pet sitter.

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Haley N.
Sitter Profile Image: Sofia H.
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Sofia H.
from
$22
per visit
5.0 out of 5 stars
95 reviews
23 repeat clients
3 years of experience
Near South Side, Chicago, IL, 60605

Sofia was amazing with our kitties during their first home alone weekend! They’re usually quite timid but Sofia was so sweet and calm that they accepted her right away. She also takes the most amazing photos to keep us updated! We will definitely be rebooking in the future :)

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Dora Z.
Sitter Profile Image: DEMIN Z.
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DEMIN Z.
from
$20
per visit
5.0 out of 5 stars
115 reviews
35 repeat clients
5 years of experience
Loop, Chicago, IL, 60605

Demin was great with my cat. I can tell that she's a excellent pet sitter! She send my updates and photos of Penelope every time. I found my house and cat in perfect conditions. I would definitely recommend her !

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Melissa A.
Sitter Profile Image: Angela E.
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Angela E.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
67 reviews
5 repeat clients
20 years of experience
Lower West Side, Chicago, IL, 60616

About: I have 2 cats at the moment. One is 9 and the other is 6. I have experience with senior cats as well. I have experience with almost everything except any sort of medical injections a cat may need.

Sitter Profile Image: Morgan L.
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Morgan L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
252 reviews
57 repeat clients
22 years of experience
Near West Side, Chicago, IL, 60606

I love her so much! My cat even more. And she’s a really shy and scaredy cat, but she lights up every time she sees Morgan. I can always go out of town, and rest easy knowing Morgan will always come and take great care of her.

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Zulma C.
Sitter Profile Image: David K.
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David K.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
160 reviews
51 repeat clients
25 years of experience
Near South Side, Chicago, IL, 60616

It’s so great having someone you can trust to look after your pets with a great deal of care and attention to detail! David is a great communicator and all around excellent and reliable pet sitter!

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Amy P.
Sitter Profile Image: Giancarlo C.
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Giancarlo C.
from
$18
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
20 years of experience
Loop, Chicago, IL, 60605

Giancarlo provided excellent care for our dog Beau. It allowed us to have a worry free weekend. Will definitely rebook in the future!

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Noura C.
Sitter Profile Image: Ruari H.
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Ruari H.
Star Sitter
from
$9
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
5 years of experience
Bridgeport, Chicago, IL, 60616

Ruari was very responsive and sent photos to make certain to me that everything was good for our pet. Would recommend to anyone

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Will B.
Sitter Profile Image: Rachel S.
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Rachel S.
from
$28
per visit
5.0 out of 5 stars
117 reviews
41 repeat clients
15 years of experience
Loop, Chicago, IL, 60605

Rachel was super responsive. She was very detail-oriented in understanding how to best care for my cat when she came by to meet him. She was also very flexible in accommodating an add-on visit during the booking. We got tons of photos when she stopped by. I would highly recommend Rachel!!

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Maitri P.
Sitter Profile Image: Madison J.
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Madison J.
from
$26
per visit
5.0 out of 5 stars
28 reviews
14 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

Madison is a terrific sitter for my Ragdoll cat! She’s kind and very thoughtful and is someone who is very dependable. She goes the “extra mile” to help me out! I highly recommend her to care for your pet!

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Donna M.
Sitter Profile Image: Lilly A.
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Lilly A.
from
$28
per visit
5.0 out of 5 stars
61 reviews
30 repeat clients
30 years of experience
Near South Side, Chicago, IL, 60605

Lilly took amazing care of our two cats over an extended trip away! She provided us with great updates and went above and beyond when our cats were a little boisterous with the toilet paper ;) I trust her completely and she is extremely reliable. I knew that our cats were safe in her care. We will definitely book her again!!!

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Emi B.
Sitter Profile Image: Acoya & Nicole R.
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Acoya & Nicole R.
from
$18
per visit
4.9 out of 5 stars
340 reviews
139 repeat clients
11 years of experience
Chicago, IL, 60605

I’ve booked Acoya twice and will continue to book her. She’s super reliable and attentive. Always spends the time with my cats even when they give her the cold shoulder, and makes sure everything is topped off for them. I always feel better leaving my cats knowing that I can have Acoya come visit them.

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Tyson W.
Sitter Profile Image: Liz A.
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Liz A.
from
$20
per visit
4.6 out of 5 stars
14 reviews
3 repeat clients
8 years of experience
Chicago, IL, 60605

Liz is great with cats, my anxious kitty stayed with her for 2 weeks and she felt comfortable almost immediately (which is not usual). She sent us frequent updates with cute pictures. I would definitely recommend Liz for cat sitting

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Laura P.
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Perfect for high energy dogs - Near South Side

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$42
per day
5.0 out of 5 stars
206 reviews
73 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley was absolutely amazing! She went above and beyond to make sure that my dog was comfortable with his stay at her house while I worked. She was very communicative, made sure to have full understanding of his care, and gave him lots of love! From the moment I dropped him off, I can tell she really cares about the pets she and her daughter care for, when I picked Echo up at the end of the day, he was so sad to leave! I’ll definitely be booking with Ashley again! :)

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Maria C.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$54
per day
5.0 out of 5 stars
106 reviews
31 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni is so amazing!! She watches our puppy when my boyfriend is traveling and I have to be in office and she sends so many updates and our puppy Sally loves seeing her every time.

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Cadence P.
Sitter Profile Image: Felipe S.
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Felipe S.
from
$37
per day
5.0 out of 5 stars
10 reviews
4 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60605

About: Hi! I’m 32 years old and live in Chicago with my sweet and wonderful cat, Simon. My connection with animals started at a very young age, with my first best friend, Pablo — a 40kg Dalmatian who was my partner in crime for many years. We took care of each other and, whenever the neighbors needed a little help, somehow we ended up taking care of most of the neighborhood too! As I grew up and moved between different countries, animals continued to be an important part of my life. Along the way, I’ve had the chance to meet and care for many different furry friends, each with their own personality and way of connecting. Today, Simon is my little companion, and I’d love to bring that same care, patience, and affection to your pets while you’re away. I know how important it is to feel confident that your pet is in good hands — and I treat every animal as an individual, with plenty of attention, respect, and love. I run my own company, so my days are busy and flexible. I always make time for animals, because they bring balance, joy, and connection. I’m comfortable caring for all kinds of animals and helping with whatever they need — from visits, walks, baths, and cleanup to playtime, companionship, and simply being there when they need someone around. I also understand that every animal has a different way of adapting to a new environment. I’m currently going through this process with Simon after moving into a new home, and it has taught me even more about how important patience and trust are. For them, everything is new: the people, the smells, the sounds, and the surroundings. It takes time to understand what feels safe. Simon loves going for walks, so we’ve been taking it step by step. Every day, we explore a little farther, stopping to sniff and investigate until a strange noise tells him, “Okay, time to go home!” 😄 Our building’s main lobby, which was once completely unfamiliar, is now a place where he feels comfortable walking around and spending time with me. And soon, I’m hoping Millennium Park will become part of our little adventure too! :) That’s the same approach I bring to every pet I care for: no rushing, no forcing — just patience, attention, and allowing them to build confidence at their own pace.

Sitter Profile Image: Annie X.
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Annie X.
from
$45
per day
4.9 out of 5 stars
159 reviews
114 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

About: ✦Now Accepting bookings for Labor Day Weekend• South Loop/Downtown Providing calm, personalized care for every pet: Whether it’s in your home or mine, I provide calm, flexible, one-on-one care tailored to each pet’s personality and comfort level. From cozy boarding stays to in-home visits and overnight house sitting, your pets will always be treated with warmth and respect. 📍 Serving Chicago and surrounding suburbs - including Downtown, South Loop, West Loop, Bridgeport, Pilsen, Chinatown, Hyde Park, Lincoln Park, and beyond. Flexible travel options available, with customized arrangements for extended distances. 🐾 My Journey with Purrfect Pet Sit 🐾 Since 2019, I’ve provided trusted, professional pet care for busy Chicago professionals and families. With over six years of experience and many ⭐⭐⭐⭐⭐ reviews, I specialize in creating a stress-free, high-quality experience for both pets and owners. I specialize in cat sitting, small and medium breed, and senior pet care, with experience in administering oral and topical medications. I’m also open to caring for large dogs after a Meet & Greet, to ensure a good fit between each other. 🤝Meet & Greet Policy Meet & Greet is required for all new clients before confirming a booking. This step allows us to review care details, daily routines, home logistics, key access if needed, and overall fit in person, including how your pet and I interact. Scheduling details will be discussed during the inquiry process. 📸💬 Daily Photo & Text Updates You’ll receive regular photo and text updates, so you can travel or work with peace of mind knowing your furry family is happy and safe at my care. I can’t wait to meet your pets and make their time truly Purrfect! 🐾💛 🌞 Schedule & Availability I work full-time with a hybrid schedule in eCommerce, with some days onsite in the western suburb Lombard and others working from home in the city. Because I regularly commute and am comfortable with travel, I’m open to overnight house sittings and extended stays beyond my immediate area when everything is a good fit. 🐾 Drop-in visits: Available early mornings before work and/or evenings after work, depending on location and care needs. Exact visit times cannot be guaranteed, but I always aim to stay within a reasonable time window and will communicate updates as needed. Flexibility is required in terms of visit time. 🏠 House sittings: My standard rate covers overnight care from evenings through mornings and includes standard morning and evening potty walks, plus a final potty break before bedtime. Daytime hours, extended exercise walks, and constant care are not included in the base rate and may require additional fees depending on care needs and scheduling. 🚗Pick-up / Drop-off: Available upon request for repeat clients or when schedules align with my Lombard–Chicago commute route. 🐕 Boarding & daycare: Limited spots available - please message to confirm availability. 🏡 Home Environment & Safety Calm, cozy home with fenced yard and pet - friendly setup - a safe, peaceful space for every guest to relax, play, and rest comfortably during their stay.

Sitter Profile Image: Vivian N.
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Vivian N.
from
$35
per day
5.0 out of 5 stars
11 reviews
8 repeat clients
7 years of experience
Near South Side, Chicago, IL, 60605

Vivian was amazing! Communicating with her was seamless and she took awesome care of my girl Maya. I loved getting pics and videos of Maya playing with her adorable pup Dior. I would def recommend her to anyone in a heartbeat. Thanks for being such a great sitter.

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Tenzin W.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per day
4.9 out of 5 stars
29 reviews
8 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Timothy is our puppy’s favorite sitter (and ours too!). It’s clear he really understands and empathizes with dogs of all ages and sizes. We’ve had multiple stays at Timothy’s place, and every time our dog comes home happy, well-cared for and occasionally having made new dog friends! We especially appreciate the way he handles our rambunctious labrador puppy- calm, kind, and confident. It’s such a relief knowing she’s in good hands. We’re grateful to have found him, highly recommend!

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Eric F. R.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$32
per day
5.0 out of 5 stars
48 reviews
17 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea took great care of our elderly, special-needs dog with awesome communication

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Gail O.
Sitter Profile Image: Carmina E.
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Carmina E.
from
$60
per day
4.9 out of 5 stars
14 reviews
4 repeat clients
8 years of experience
Loop, Chicago, IL, 60605

Moose had a great time with Carmina this weekend! She was very responsive and easy to coordinate with, we will definitely be using her again!

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Audrey P.
Sitter Profile Image: Jaclyn B.
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Jaclyn B.
Star Sitter
from
$38
per day
5.0 out of 5 stars
9 reviews
4 repeat clients
3 years of experience
Loop, Chicago, IL, 60605

Jaclyn was super prompt in her responses, kind, and super sweet for my dog! Communication was excellent, and she made sure that Billie not only was taken care of but that she met her social and physical exercise for the day with enrichment time at the farmers market! I would definitely rebook her again and recommend Jaclyn to anyone!

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Anne N.
Sitter Profile Image: Gabriel V.
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Gabriel V.
from
$33
per day
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Bridgeport, Chicago, IL, 60608

Gabriel was an excellent dog sitter for Walnut. He was attentive, patient, and very professional throughout the entire experience. He communicated clearly, provided updates, and always confirmed details, which gave me great peace of mind. Walnut seemed very happy and comfortable with him, and it was clear he genuinely enjoyed spending time with Gabriel. I truly felt that Walnut was in good hands. I would definitely recommend Gabriel and would love for him to continue sitting for us in the future.

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Mina R.
Sitter Profile Image: Patrick & Susan C.
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Patrick & Susan C.
from
$40
per day
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Near South Side, Chicago, IL, 60605

About: I’ve had dogs for over 25 years - from puppyhood through their senior days. My last dog passed away late last year, and now we’re looking forward to taking care of other people’s dogs! My wife and are retired and on the days we accept reservations will have plenty of time to take your dog on long walks and play! We have a single-floor apartment in the South Loop, We can accommodate a crate if your dog uses one. We will always follow your guidance on how much or little your dog prefers to interact with other dogs and people.

Sitter Profile Image: Thomas Q.
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Thomas Q.
from
$30
per day
5.0 out of 5 stars
3 reviews
35 years of experience
Near South Side, Chicago, IL, 60616

About: I have experience caring for pets and understand the importance of providing them with patience, attention, and a safe environment. My responsibilities have included feeding pets according to their schedules, providing fresh water, taking dogs for walks, cleaning up after them, and giving them plenty of exercise and companionship. I am comfortable following specific care instructions and paying close attention to each pet’s individual needs and behavior. I am dependable, responsible, and genuinely enjoy spending time with animals. After spending 33 years working in corporate America, I am excited to begin a new chapter in life—one centered around spending more time with animals and providing them with loving, dependable care. I developed a strong sense of responsibility, reliability, patience, and attention to detail. I understands the importance of being trustworthy and following through on commitments, qualities that are just as important when caring for someone’s beloved pets. Now retired, I have the time and flexibility to give pets the attention, companionship, exercise, and care they deserve. I enjoy getting to know each pet’s unique personality and creating a safe, comfortable environment where they can feel happy and relaxed. For me, pet care is more than simply a responsibility—it’s an opportunity to enjoy the companionship of animals while giving their owners peace of mind that their pets are in caring and capable hands. Your pet’s safety, comfort, and happiness are my top priorities. My loft provides a clean, comfortable, and welcoming environment where pets can relax and feel at home. When your pet stays with me, you can feel confident knowing they’re receiving attentive, loving care in a safe home away from home. My goal is simple: for you to have peace of mind and for your pet to feel loved, secure, and comfortable.

Sitter Profile Image: Anna N.
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Anna N.
from
$65
per day
5.0 out of 5 stars
27 reviews
5 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

Anna was an amazing dog sitter! She sent us great pictures and updates throughout the day, was very communicative, and Moose seemed to have an amazing time with her! 10/10 would use her again!

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Audrey P.
Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Star Sitter
from
$53
per day
5.0 out of 5 stars
224 reviews
53 repeat clients
11 years of experience
Near South Side, Chicago, IL, 60605

Katrina was great. Very good communication, lots of updates and pictures, and had an extra harness when ours broke. Would highly recommend!

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AJ S.
Sitter Profile Image: Pamela P.
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Pamela P.
from
$36
per day
5.0 out of 5 stars
12 reviews
4 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60605

I have an unexpected conference to attend in Chicago. I needed someone to watch my baby for me. Pamela was quick in her response, flexible and very caring. She literally save me. Thanks again

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Hawa G.
Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$49
per day
5.0 out of 5 stars
72 reviews
23 repeat clients
50 years of experience
Near North Side, Chicago, IL, 60611

Fantastic experience with Steven! Very prompt in communication and I could tell he genuinely loves dogs. Mochi was happy during his time with them. Highly recommend

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Divyasha R.
Sitter Profile Image: Dani B.
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Dani B.
from
$33
per day
5.0 out of 5 stars
45 reviews
11 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60605

About: Hi, I’m Dani😄. I recently discovered Rover and decided to join the app! Two populations in the world I enjoy spending my time with are individuals with disabilities and animals. Along with my passion in spending time with dogs, I am a Registered Behavior Technician and provide 1:1 direct therapy with individuals with disabilities. My niche is kiddos with Autism and other neurological/developmental disorders. I am currently working towards my Masters in Applied Behavior Analysis. I enjoy taking dogs on long walks, finding fun activities to do in my area (if your dog is into that), and overall providing comfort and a safe environment for your dog to roam in, play in, and be sure to have his needs met. I’m all about making sure families feel comfortable and trust leaving their doggos with me:) I normally like taking dogs out around every two hours. Depending on the age of the puppy, I may go outside more frequently if necessary. I enjoy catering to dogs and their specific routine/needs. My dog is also very flexible in adapting to other dog’s routines which has always been nice. I love to provide as much comfort as I can when families leave their dogs with us. My home has become a free for all for dogs to get comfortable. I love to provide dog enrichment as well. I am always keeping a bowl of water out for the dog as well as sticking to your dog’s feeding schedule. I allow dogs to lay on my couch, my dog’s beds, and even my bed as well.

Sitter Profile Image: Ksenia D.
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Ksenia D.
Star Sitter
from
$40
per day
4.9 out of 5 stars
46 reviews
21 repeat clients
4 years of experience
Near North Side, Chicago, IL, 60611

I had my dog Mildred with me while in town for a conference. Ksemia was super responsive, vey flexible, and took such great care of Mildred! Mildred took to her immediately and I got updates of all her adventures. I will definitely work with her again when I'm in Chicago!

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Jenny L.
Sitter Profile Image: Katie C.
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Katie C.
from
$65
per day
5.0 out of 5 stars
29 reviews
6 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60605

About: I am a highly experienced and passionate caretaker for furry friends. With 3 dogs and 1 cat of my own, I have a lifetime of experience in taking care of animals. I am particularly knowledgeable in geriatric care and puppy training, ensuring that animals of all ages receive the specialized care and attention they need. Pet care is essential in my household and is a top priority for my daily routine to ensure my fur-babies are well-fed, nurtured, happy, and healthy! At the moment, I have 3 dogs (Mini Aussie, Geriatric Chihuahua, and a Geriatric Lab) with one orange cat! I love animals naturally and enjoy spending time energetically with animals and catering to their needs.

Sitter Profile Image: Czarina H.
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Czarina H.
from
$55
per day
5.0 out of 5 stars
8 reviews
2 repeat clients
17 years of experience
Near West Side, Chicago, IL, 60607

About: I grew up with family dogs and have had mine since he was 8 weeks old (he will be 17 years old this August!). Experience with puppies through senior dogs. Large breeds and small! Would love to take care of yours. I work full time from home, so I have ample amount of time to hang out with your pups (no matter the age, dogs are forever pups in my eyes!). I have an almost 17 year old pup who naps most of the day but is always excited for his walks! I live in a low traffic area and just down the street from a fenced grass area we play in. In case there’s rain, I have a covered area to take the pups out so they still get some fresh air.

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More than 1.6 million
pets enjoyed cuddles and care from sitters on Rover1

Adventure-ready dog walkers - Near South Side

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Patrick & Susan C.
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Patrick & Susan C.
from
$20
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Near South Side, Chicago, IL, 60605

Patrick so great and patient with my pup Jack! He takes his time making sure his collar is placed correctly and takes very good care of him! I will def be booking again!

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Alexis R.
Sitter Profile Image: Anthony M.
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Anthony M.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
548 reviews
61 repeat clients
25 years of experience
Chicago, IL, 60616

Anthony is very professional and experienced. My dog is still learning how to behave during walks and Anthony did a great job keeping him under control and safe. He was also very nice and flexible to do a meet and greet before the first walk to meet my dog.

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ana G.
Sitter Profile Image: Mariam A.
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Mariam A.
from
$14
per walk
5.0 out of 5 stars
41 reviews
13 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Strong communicator and sweet energy with my pets. I was nervous about hiring a dog walker and Mariam helped put me at ease by demonstrating her trustworthiness.

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Heather M.
Sitter Profile Image: Hale T.
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Hale T.
from
$20
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
45 years of experience
Near South Side, Chicago, IL, 60616

About: I have shared my life with cats since childhood, which has given me a deep, natural understanding of their unique languages and temperaments. As a current cat owner myself, I know that cats are not just pets—they are family. I understand how important it is for them to maintain their daily routines and feel safe and loved while their owners are away. I believe communication is key to a pet owner’s peace of mind. I always provide regular photo and video updates so you can see exactly how your furry friend is doing. I will treat your home with respect and your cat with the same love and devotion I give to my own. I have a fully flexible schedule and am available 7 days a week, including weekends and holidays. Whether you need a one-time visit or a long-term sitter, I can easily accommodate your cat’s routine. I offer a safe, calm, and fully cat-proofed home environment where your cat will be treated like family. My home is a dedicated 'cat-friendly' space with plenty of cozy spots for napping and safe areas for play. I take safety very seriously; all windows are secured, and there are no hazardous plants or small objects accessible. Since I have my own cat, I am experienced in slow, stress-free introductions if needed, or I can provide a completely separate, quiet room if your cat prefers to be alone. I maintain a very high standard of cleanliness, with litter boxes scooped multiple times a day. Your cat will have my full attention and a peaceful atmosphere throughout their stay

Sitter Profile Image: Angela E.
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Angela E.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
67 reviews
5 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

I have a reactive dog and Angela was very understanding of the situation. I did my best to provide directions, so that and her experience with reactive dogs made it so taking out my dog was a breeze. Definitely will be booking Angela in the future!

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Oscar R.
Sitter Profile Image: Gabriela M.
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Gabriela M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
30 reviews
15 repeat clients
3 years of experience
Chicago, IL, 60605

Gabriela is the most reliable dog walker I’ve had! She is so attentive to my dog and he just loves his fun outdoor adventures

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Iman P.
Sitter Profile Image: Sofia H.
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Sofia H.
from
$21
per walk
5.0 out of 5 stars
95 reviews
23 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60605

Sofia was wonderful to work with and always very communicative during walks! She was very patient with my building when there were issues with accessing the apartment. I will definitely have her walk Blue again in the future!

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Swetha V.
Sitter Profile Image: Hallie B.
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Hallie B.
from
$19
per walk
5.0 out of 5 stars
70 reviews
27 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

10/10 super kind and my pup was immediately excited to meet her for the first time, which I think is an EXCELLENT SIGN! Would highly recommend!

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Ashley F.
Sitter Profile Image: Thomas Q.
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Thomas Q.
from
$20
per walk
5.0 out of 5 stars
3 reviews
35 years of experience
Near South Side, Chicago, IL, 60616

About: I have experience caring for pets and understand the importance of providing them with patience, attention, and a safe environment. My responsibilities have included feeding pets according to their schedules, providing fresh water, taking dogs for walks, cleaning up after them, and giving them plenty of exercise and companionship. I am comfortable following specific care instructions and paying close attention to each pet’s individual needs and behavior. I am dependable, responsible, and genuinely enjoy spending time with animals. After spending 33 years working in corporate America, I am excited to begin a new chapter in life—one centered around spending more time with animals and providing them with loving, dependable care. I developed a strong sense of responsibility, reliability, patience, and attention to detail. I understands the importance of being trustworthy and following through on commitments, qualities that are just as important when caring for someone’s beloved pets. Now retired, I have the time and flexibility to give pets the attention, companionship, exercise, and care they deserve. I enjoy getting to know each pet’s unique personality and creating a safe, comfortable environment where they can feel happy and relaxed. For me, pet care is more than simply a responsibility—it’s an opportunity to enjoy the companionship of animals while giving their owners peace of mind that their pets are in caring and capable hands. Your pet’s safety, comfort, and happiness are my top priorities. My loft provides a clean, comfortable, and welcoming environment where pets can relax and feel at home. When your pet stays with me, you can feel confident knowing they’re receiving attentive, loving care in a safe home away from home. My goal is simple: for you to have peace of mind and for your pet to feel loved, secure, and comfortable.

Sitter Profile Image: Anastasiia M.
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Anastasiia M.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
174 reviews
40 repeat clients
17 years of experience
Chicago, IL, 60602

Ruthie loves seeing Anastasiia! While they don’t see each other very often, they became good friends and we love having Anastasiia care for Ruthie whenever possible.

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Ashley A.
Sitter Profile Image: Eunice Y.
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Eunice Y.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
78 reviews
29 repeat clients
4 years of experience
Loop, Chicago, IL, 60607

Eunice was so sweet with Willow. She took the time to get to know her and made her feel comfortable which I really appreciated. She also took the time to chat with me about the walk which made us both feel at ease. Will book again!

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Tirzah W.
Sitter Profile Image: Julia B.
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Julia B.
from
$20
per walk
5 years of experience
Near South Side, Chicago, IL, 60605

About: I have had cats, dogs, fish, and a chinchilla since I was 10 years old, so I truly take care of pets like they're people! I work from Monday to Thursday full time (7am - 5:30pm), so I am free during weekday evenings. Otherwise, I am free from Friday to Sunday! I live in a safe, managed apartment and I have two cats. I can easily move my cats to another room to avoid conflict between our pets.

Sitter Profile Image: Alexander P.
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Alexander P.
from
$20
per walk
5.0 out of 5 stars
3 reviews
10 years of experience
Near South Side, Chicago, IL, 60605

About: I've been around dogs for most of my life and have always owned them, so caring for them comes naturally to me. My experience comes from raising my own dogs and looking after friends' and family members' pets while they were away. I've cared for both small and medium-sized breeds, including Yorkshire Terriers, French Bulldogs, Pomeranians, and Chow Chows. I currently have two dogs of my own, and because I work from home, I'm able to provide consistent supervision, companionship, potty breaks, and plenty of attention throughout the day. My two dogs are friendly, energetic, and well-socialized. They love meeting new furry friends and help create a fun, welcoming environment where visiting dogs can enjoy companionship, playtime, and social interaction if they're comfortable with it. I always make introductions carefully and respect each dog's individual personality and comfort level. Every dog has their own personality and routine, and I take the time to make sure they feel comfortable, safe, and cared for. Whether your pup enjoys playing, relaxing around the house, or simply being close to people, I'll do my best to make their stay feel like a home away from home. I work full time from home, which allows me to provide consistent care, supervision, and companionship throughout the day. Because I'm home, your pup won't be left alone for long periods and will have plenty of opportunities for potty breaks, playtime, exercise, and affection. I'm available for boarding seven days a week and can easily accommodate your dog's regular routine, including feeding schedules, walks, medication (if needed), and plenty of one-on-one attention. My two friendly, energetic dogs also enjoy making new friends and can provide companionship and playtime for dogs that enjoy socializing, while I always respect the comfort level and personality of every guest. Your dog's safety, comfort, and happiness are my top priorities. Since I work from home, I'm able to provide close supervision throughout the day and make sure every dog receives plenty of attention and care. I follow each owner's instructions carefully, including feeding schedules, potty breaks, walks, medications (if needed), and any special routines to help your pup feel at home. My home is a safe, clean, and welcoming environment where dogs can relax, play, and feel comfortable. My two friendly, well-socialized dogs are accustomed to being around other dogs, and I always introduce new guests gradually to ensure everyone is comfortable. I closely monitor all interactions and never force dogs to socialize if they prefer their own space. I know how important it is to stay connected while you're away, so I'll keep you updated with regular messages and photos so you can have peace of mind knowing your furry family member is happy, safe, and well cared for.

Sitter Profile Image: Alain R.
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Alain R.
from
$17
per walk
4 years of experience
Near South Side, Chicago, IL, 60616

About: I’ve taken care of dogs of all sizes and ages, including administering medication for special needs doggies. I’ve had dogs all my life and absolutely love them! I just moved to Chicago and I’m only working part-time so I have plenty of time and a flexible schedule to take care of your pups. I am happy to continue any practices you take with your dog to help them feel safe and comfortable while you’re away. I also like setting up an introductory meeting with the owner so the dog can familiarize themselves with me while in the presence of someone they trust.

Sitter Profile Image: Tarel D.
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Tarel D.
from
$15
per walk
4.8 out of 5 stars
13 reviews
6 repeat clients
20 years of experience
Loop, Chicago, IL, 60605

Tarel has been absolutely wonderful with my dog, Kanan! From the first walk, it was clear that Tarel is caring, dependable, and genuinely loves animals. He takes the time to make sure Kanan gets plenty of exercise and attention, and always gives thoughtful updates and photos after each visit. I really appreciate his punctuality and communication and it makes scheduling so easy and gives me total peace of mind when I’m away. Kanan is always happy and relaxed after his walks, which says it all. I highly recommend Tarel to anyone looking for a responsible and caring dog walker!

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Lawrence P.
Sitter Profile Image: Erin K.
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Erin K.
from
$30
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
25 years of experience
Near South Side, Chicago, IL, 60612

Erin is just amazing with my senior dog. In such a short time, my dog has become friends with her. Erin is very professional, punctual and takes full care of my dog when walking him.

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Vikas G.
Sitter Profile Image: Lillian M.
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Lillian M.
from
$25
per walk
5.0 out of 5 stars
32 reviews
9 repeat clients
13 years of experience
Armour Square, Chicago, IL, 60616

Lillian has been great with my dogs and very communicative throughout the walks. She took the time to make sure they were comfortable, shared updates and photos, and went above and beyond with their care. I really appreciated her flexibility and willingness to work with my schedule, especially while I was out of town. I felt confident knowing my dogs were in good hands, and I would absolutely recommend her to other pet parents.

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Carla T.
Sitter Profile Image: Natasha N.
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Natasha N.
from
$15
per walk
5.0 out of 5 stars
2 reviews
3 years of experience
Chicago, IL, 60605

About: I became the go to pet sitter for my friends in grad school. My work is flexible so I would spend a lot of time building that experience that I didn’t have growing up when it came to pets. It has been an incredible journey caring for and looking after pets and I am excited to continue to hone in on the skills and expertise that I have 💕 My work is hybrid so I have very open weekdays where work from home up until I have to commute to do in person work from 5-10pm. Weekends are completely free with me so I’ll spend it hanging out with friends, catching up on household chores, or just resting from the long week. I have a lot of time to care for pets as the work I do is more marketing, communicative, strategic work that is self paced and guided so I can always take breaks when need be. The area that I live in is incredibly pet friendly and there are a multitude of parks a places where a pet can run freely.

Sitter Profile Image: Azure D.
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Azure D.
from
$20
per walk
5.0 out of 5 stars
4 reviews
15 years of experience
Near South Side, Chicago, IL, 60605

About: I’ve been around animals my entire life, growing up in a home with several dogs and gaining hands-on experience caring for them from a young age. Over the years, I’ve become very comfortable with all aspects of pet care, including administering daily medications and following specific routines to keep pets healthy and stress-free. I’m especially attentive to each animal’s unique needs my own pup, for example, has sensitivities, so I understand how important it is to monitor diet, behavior, and environment closely. In addition to dogs, I also have experience with a variety of animals, as my mom rehabilitated exotic wildlife while I was growing up. That background taught me patience, adaptability, and how to properly care for animals that require extra attention. What sets me apart is how much I prioritize each pet’s health and quality of life. I personally walk my own dog four times a day and bring that same level of care, attention, and routine to every dog I work with. I pride myself on being reliable, detail-oriented, and genuinely loving toward every pet I care for, and I specialize in working with puppies. I work from home, which allows me to be present and attentive to your dog throughout the day. This setup is ideal for pets who need consistent companionship, frequent potty breaks, or a little extra reassurance while you’re away. Whether your dog thrives on attention, has separation anxiety, or simply enjoys having someone nearby, I’m able to provide a calm, supervised environment with plenty of interaction and care. I live in a secure apartment on the third floor with easy ground-level access for quick and convenient potty breaks. My building also offers a dedicated outdoor dog area on the 17th floor, providing a safe and clean space for additional exercise and fresh air. I prioritize safety, routine, and comfort in my home, and I’m happy to follow any specific instructions you have for your pet’s care. To keep you fully at ease, I provide daily, detailed updates with photos so you always know how your dog is doing.

Sitter Profile Image: Acoya & Nicole R.
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Acoya & Nicole R.
from
$30
per walk
4.9 out of 5 stars
340 reviews
139 repeat clients
11 years of experience
Chicago, IL, 60605

Brynn was very grateful to have Acoya stop by and give him a potty break and some loving!! She sent a photo and a very accurate description of Brynn being his stubborn self that gave us a good laugh!

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Alicea A.
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Over 980,000
dogs traded couch time for play time with Doggy Day Care on Rover1

Large dog specialists near you - Near South Side

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
206 reviews
73 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley is amazing and was able to take my girls on short notice! They love spending time with Ashley and her daughter Marina and I know they are super well cared for! 🐾💜

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Angie S.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
149 reviews
6 repeat clients
3 years of experience
Near South Side, Chicago, IL, 60605

Ania was great! Very professional, kind and reliable sitter. Simba had a wonderful stay with Ania! Lots of photo/video updates, I can see my dog was truly well taken care of! Will definitely book with her again in a future 💕

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Arina U.
Sitter Profile Image: Jenna M.
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Jenna M.
Star Sitter
from
$53
per night
5.0 out of 5 stars
102 reviews
24 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

She was an amazing choice and Bailey loved being with her and her doggo. If you want a safe sitter and one that will give all their love and attention to them, she is the one! I will most definitely be rebooking again.

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Richard G.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.9 out of 5 stars
29 reviews
8 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Timothy was a wonderful sitter ! He shared updates and photos regularly and gave my dog extra food because I didn’t pack enough. He was also very gracious to let me extend my booking on short notice due to travel delays. Highly recommend Timothy and hope we can book with him again !

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Michelle C.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
392 reviews
185 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Teddy is our 150lb Bullmastiff and EK and her family welcomed him like the rest of the tiny tots that are looked after daily. She is trustworthy and reliable. We hadn't been on a real vacation in 2yrs we had no issues or worries while gone.

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Susan L.
Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$58
per night
5.0 out of 5 stars
72 reviews
23 repeat clients
50 years of experience
Near North Side, Chicago, IL, 60611

Steven is great. Sends me daily reports with pics. My flight was delayed and he was extremely flexible in helping me out with an extended stay.

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Amy A.
Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
186 reviews
73 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

I have been going to Bola for quite some time now and she is very accommodating when it comes to my 90 pound Goldendoodle. I truly appreciate her flexibility and support in watching him from time to time as I navigate my first pregnancy,

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Christina E.
Sitter Profile Image: Samantha M.
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Samantha M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
30 reviews
9 repeat clients
10 years of experience
West Town, Chicago, IL, 60642

Samantha and Rosie were amazing! She sent such cute pictures and was very accommodating. I will definitely book again when I need a sitter :)

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Greta F.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$55
per night
5.0 out of 5 stars
106 reviews
31 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni did an amazing job taking care of our fur babies! She was responsive, asked questions, and kept us updated while we were away on our vacation. It was a first time boarding our pets and Anni did a great job easing any concerns we had. Our pets were at ease with her and felt very at home in her space. Would definitely recommend!

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Alyson P.
Sitter Profile Image: Jennifer N.
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Jennifer N.
Star Sitter
from
$50
per night
4.9 out of 5 stars
281 reviews
128 repeat clients
6 years of experience
Lower West Side, Chicago, IL, 60608

Booking Jennifer for dog sitting was a fantastic decision. Her attentiveness to my dog gave me complete peace of mind, and her super quick responses to my messages were a huge plus. I'd absolutely choose her again for future sitting needs.

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Soleil L.
Sitter Profile Image: Christina L.
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Christina L.
from
$55
per night
5.0 out of 5 stars
64 reviews
21 repeat clients
15 years of experience
West Town, Chicago, IL, 60622

Amazing sitter for our dog! This was our first time leaving her for so many days not with family. Christina was great about sending updates and took wonderful care of Gobi. Will absolutely book with her again!!

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Pranshul G.
Sitter Profile Image: Fred C.
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Fred C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
45 reviews
9 repeat clients
25 years of experience
Lower West Side, Chicago, IL, 60616

Fred was absolutely wonderful to coordinate with, super responsive! And he sent daily updates and pics of our sweet boy. Dante was the right amount of excited to see us, and I think he definitely enjoyed his time with Fred. Thank you so much!!!!

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Antonia H.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
375 reviews
102 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

Katie was a great sitter. She frequently updated and let me know how my dog was. He seemed every happy at her place. Her dog is always very friendly and got along just fine with mine. Thanks again :)

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Nikita J.
Sitter Profile Image: Hannah T.
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Hannah T.
from
$50
per night
5.0 out of 5 stars
13 reviews
1 repeat client
25 years of experience
Near West Side, Chicago, IL, 60661

Hannah was fantastic with my dog, Callie! She took her out to her farm, which she loved, and kept me updated with plenty of pictures and messages throughout the stay. Hannah even gave her a bath before bringing her back to the city, which was a thoughtful touch. I could tell Callie was well cared for and had a great time. I will definitely be booking with Hannah again!

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Mitchell G.
Sitter Profile Image: Barbara R.
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Barbara R.
from
$45
per night
4.9 out of 5 stars
89 reviews
32 repeat clients
16 years of experience
West Town, Chicago, IL, 60642

Barbara is a great dog sitter! Kaiser had a wonderful time with her. She was always in touch, kept us updated, and made us feel very comfortable while we were away. Highly recommend!

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Alina
Sitter Profile Image: Thomas Q.
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Thomas Q.
from
$30
per night
5.0 out of 5 stars
3 reviews
35 years of experience
Near South Side, Chicago, IL, 60616

Thomas is such a great sitter! He sent us daily updates on how our pup Maui was doing. From the start, he welcoming and communicative. Maui was very happy with him! Can’t recommend Thomas enough!

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Samantha M.
Sitter Profile Image: Lech S.
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Lech S.
Star Sitter
from
$49
per night
4.9 out of 5 stars
104 reviews
40 repeat clients
10 years of experience
West Town, Chicago, IL, 60647

Lech was brave enough to take care of my bulldogs for three days. He did a great job checking in and sending pics. More importantly, when Francis and Mr Wrinkles got home, they didn't seem to have been stressed out or anything, which has happened with sitters in the past. Further, Lech was able to take care of my "special needs" dog who is def. And, he was available to pick up and drop off the pair which saved me tons of time. Will def look to book again!

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Micheil L.
Sitter Profile Image: Angel V.
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Angel V.
Star Sitter
from
$47
per night
5.0 out of 5 stars
123 reviews
34 repeat clients
15 years of experience
Humboldt Park, Chicago, IL, 60624

Angel was definitely a star sitter! Was out of pocket for a few days and he gave me regular updates on how my pup was doing. 10/10 would book again!

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John F.
Sitter Profile Image: Jacob G.
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Jacob G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
20 years of experience
Lake View, Chicago, IL, 60657

Freddie had a great time with Jacob and Clover! Jacob was responsive and sent updates throughout the weekend.

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Lizzie G.
Sitter Profile Image: Nina C.
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Nina C.
Star Sitter
from
$54
per night
5.0 out of 5 stars
48 reviews
8 repeat clients
10 years of experience
West Town, Chicago, IL, 60647

Can’t thank Nina enough for the awesome care she took of my dog for a holiday weekend! She sent so many great pics and videos that made it clear my dog was having a great time. I am THRILLED I found her on Rover!!

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Kady T.
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