Personalized care for your dog or cat - Grand Boulevard

Highly-rated overnight sitters - Grand Boulevard

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

1 / 1
Sitter Profile Image: Ksenia D.
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Ksenia D.
Star Sitter
from
$46
per night
5.0 out of 5 stars
26 reviews
7 repeat clients
4 years of experience
Near North Side, Chicago, IL, 60611

Ksenia took such wonderful care of my dog - it was clear she truly understood his needs and personality. She’s incredibly gentle, patient, and attentive, which made a huge difference. I especially appreciated the regular updates and photos, which gave me so much peace of mind. It’s rare to find someone so reliable and genuinely caring - I would absolutely trust her again without hesitation.

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Manisha S.
Sitter Profile Image: Kyla G.
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Kyla G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
65 reviews
28 repeat clients
20 years of experience
West Elsdon, Chicago, IL, 60632

So thankful for Kyla & Barbara (her mom) for taking care of Drogo! Drogo’s very happy. They have updates with photos & videos everyday. They are very sweet & accommodating. We even did a video call because our daughter missed Drogo so much! We’ll definitely book them again when we visit the area. ❤️?

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Aylnn G.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
20 reviews
5 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
372 reviews
175 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Liz and her family were so good to Tyson. He loved staying there, and they really welcomed him into their family. He's the kind of dog who thrives off of attention and love, and they gave him plenty of both. I also got great updates and pictures which really made me feel like he was in good hands. I will definitely book with them again, if possible!

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Mallika T.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was a wonderful sitter! My dog was well cared for and had a blast. I will book with her again !

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Michelle C.
Sitter Profile Image: songen f.
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songen f.
Star Sitter
from
$55
per night
5.0 out of 5 stars
14 reviews
8 repeat clients
11 years of experience
Loop, Chicago, IL, 60605

Songen did a great job taking care of Sundae while I went on a trip. She provided multiple updates every day and provided plenty of photos and videos. She made me feel so comfortable and that Sundae was in great hands.

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Cheryl G.
Sitter Profile Image: Mia L.
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Mia L.
Star Sitter
from
$46
per night
5.0 out of 5 stars
27 reviews
11 repeat clients
10 years of experience
Near North Side, Chicago, IL, 60611

Mia has been wonderful. She is reliable, kind, and clearly cares deeply about the dogs she works with. Her communication is excellent; she keeps us updated, responds quickly, and sends thoughtful notes, which gives us a lot of peace of mind. We also really appreciate the level of care she provides. She is attentive to our dog’s needs, patient, and responsible, and it’s clear our dog feels comfortable and happy with her. Mia goes above and beyond by being punctual, trustworthy, and genuinely invested in making sure each walk is safe, enjoyable, and positive. We’re very grateful to have found her.

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Mariana S.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
248 reviews
86 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Tamara was absolutely amazing with Frankie! From the moment I dropped her off, I could tell she was in safe, caring hands. She kept me updated with regular messages and photos, which really put my mind at ease while I was away. It’s clear she truly loves and understands dogs, and Frankie seemed so happy and comfortable in her care. I couldn’t have asked for a better experience, and I’ll definitely be booking with her again!

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Yahya M.
Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Star Sitter
from
$55
per night
5.0 out of 5 stars
181 reviews
47 repeat clients
11 years of experience
Near South Side, Chicago, IL, 60605

Katrina is an amazing caregiver. Incredibly thoughtful and caring. Excellent communication. Fun pictures. I felt completely comfortable with Katrina watching my little one 🐶🙏

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Eugene C.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
188 reviews
67 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley is AMAZING with our dog Rue! She sends such sweet photos and updates, she’s flexible and responsive - we always know Rue is in great hands when we’re out of town.

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Maya H.
Sitter Profile Image: Kamiah & Casius D.
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Kamiah & Casius D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
34 reviews
23 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

Kamiah & Casius were great with my fur baby. It was my first time using a service like this and I was so nervous. Kamiah was understanding of my nerves answered all my questions. She sent daily photos and videos. She was understandable with my travel delays and when I picked my dog up she was smiling and continued to do so for the rest of the evening. There were no stress signals or behaviors from my dog and she was right back into her routine at home. Thank you for taking such great care of Macci!! Will definitely use again

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Jada J.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

OMG she was wonderful. Her space was nice and clean she checked in everyday with me I was running late she assured me it was ok my dog went on play dates and much more. I would definitely be using her every time.

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Tiffany S.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
from
$35
per night
5.0 out of 5 stars
19 reviews
14 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Cheyanne was amazing. She had great communication and my dog can be timid and not eat much at dog sitters but she didn't have that problem with her. Best sitter! Thank you

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Nicole M.
Sitter Profile Image: Ann V.
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Ann V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
128 reviews
26 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60605

Bronx (and I!) love Ann! She always takes great care of him and loves him like her own. Always super attentive and sends the cutest pictures. Thank you!!

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Czarina H.
Sitter Profile Image: Sara T.
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Sara T.
from
$40
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Lower West Side, Chicago, IL, 60608

I had a great experience with Sara. She communicated well and was really easy going. She sent pictures and videos. And our dog Boomer seemed to have a great time! I would happily book again!

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Carly R.
Sitter Profile Image: Ann-Marie H.
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Ann-Marie H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Ann-Marie is great! She is so sweet with Luka and sends great photos and updates. Our second booking with her and we plan to book her going forward every time!

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Raven C.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
132 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania is amazing! She’s checked in with pix and videos daily. My pup came home so happy and content. I’ll definitely be checking her schedule the next time I need a sitter. 10/10 ☺️

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Davinelle D.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$40
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

Cassandra took great care of my dog Ace during his 4-day stay. I can tell he had a good time hanging out with her dog, Chewy. Cassandra was a pleasure to work with and I hope to use her services again for future boarding.

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Joseph G.
Sitter Profile Image: Brandon E.
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Brandon E.
from
$42
per night
5.0 out of 5 stars
21 reviews
11 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

Brandon was awesome to work with! He kept consistent with his communication and took care of our fur baby. He’s also a trainer, so your pup is in good hands!

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Derrick V.
Sitter Profile Image: Bola A.
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Bola A.
from
$54
per night
4.9 out of 5 stars
171 reviews
62 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Bola took great care of my pup child. Rhea received lots of love and was definitely spoiled. (I can tell) lol Bola was responsive and sent updates and videos of Rhea. Rhea really likes Bryce and I hope they become long-term pup friends. I would definitely book again without giving it a second thought.

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Nicole M.
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Over 4.1 million
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Cat caregivers near you - Grand Boulevard

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

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Sitter Profile Image: Jessica G.
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Jessica G.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
New City, chicago, IL, 60609

Jessica was super great and took the time to make sure my shy kitty was comfortable! She is thoughtful and patient. Would book her again in a heartbeat!

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Hannah L.
Sitter Profile Image: Christina D.
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Christina D.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
10 years of experience
Oakland, Chicago, IL, 60653

Christina did a great job taking care of my five cats, two of whom zi have medical needs. I really appreciated her daily updates and photos of my boys.

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Susan B.
Sitter Profile Image: Amiyah W.
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Amiyah W.
from
$14
per visit
3 repeat clients
1 year of experience
Grand Boulevard, Chicago, IL, 60615

About: I've taken care of multiple cats. I even have cats of my own so I am familiar of what they like and how to care for them. I have previous experios with caring for cats who have medical needs.

Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$14
per visit
5.0 out of 5 stars
26 reviews
12 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

Jozelin did a great job with our two cats. Lots of pictures of them hanging out together. She left everything in order after her stay at our place, and we will definitely book with her again.

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Charles K.
Sitter Profile Image: Brianna B.
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Brianna B.
from
$9
per visit
5.0 out of 5 stars
6 reviews
4 years of experience
Hyde Park, Chicago, IL, 60615

Brianna was super communicative, timely, and cared well for my cat while giving detailed updates! Would book again!

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Ria M.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
38 reviews
12 repeat clients
10 years of experience
Douglas, Chicago, IL, 60653

Chelsea did an amazing job caring for my kitties over the holidays! First, I ended up booking shorter notice and Chelsea responded immediately, was flexible, and was able to accommodate me and my babies. Chelsea was a great communicator when she was caring for my kitties, she gave consistent updates about how they were doing, as well as the tasks she completed when caring for them (refilling food and water, cleaning the litter box). I really appreciated the time and effort Chelsea put into caring for my babies, especially during the holiday time. Thank you!

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Eden A.
Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
43 reviews
15 repeat clients
30 years of experience
Hyde Park, Chicago, IL, 60615

Evan was a great sitter! Communicative, considerate, and easy to work with.

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Eve F.
Sitter Profile Image: Jessy M.
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Jessy M.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
13 years of experience
Hyde Park, Chicago, IL, 60615

Jessy was very responsive and did everything I asked of her!

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Leah C.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
82 reviews
33 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Qutress was great with our shy cat, who even let Qutress pet her which is quite rare for newcomers! She was very communicative and gave us wonderful updates every day. Highly recommend!

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Luke M.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
24 reviews
10 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

Daphne was amazing with our fur babies and gave them all the love while we were gone. She was as punctual, professional and caring. She was as excellent with communication and follow up. We will use her service again knowing the dogs are taken care of.

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Petia O.
Sitter Profile Image: Sally H.
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Sally H.
from
$23
per visit
5.0 out of 5 stars
59 reviews
21 repeat clients
15 years of experience
Kenwood, Chicago, IL, 60653

Sally has been a diamond in the rough that has been my work-life balance after moving across the country. Her clear communication for a newbie to the app is refreshing, and her thoughtful care allows me to relax, knowing my cat is in good hands. I thank my lucky stars I found her!

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rosaleschristopher
Sitter Profile Image: Jasmine P.
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Jasmine P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
97 reviews
38 repeat clients
13 years of experience
Kenwood, Chicago, IL, 60615

We’re so lucky to have found Jasmine! I have a very territorial cat but her calm demeanor and patience paid off and he got comfortable with her presence.

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Maya C.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per visit
4.7 out of 5 stars
12 reviews
6 repeat clients
10 years of experience
Chicago, IL, 60653

Jasmine R was awesome. Thorough and punctual. My kitty was happy and my home was just as I left it. I will use her services again.

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Stacey S.
Sitter Profile Image: Veronica M.
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Veronica M.
from
$15
per visit
4 years of experience
Chicago, IL, 60653

About: I love taking care of cats! I will make sure your cat has playtime, a clean litter box, and the proper food to make sure they're healthy.

Sitter Profile Image: Taylor W.
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Taylor W.
from
$18
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
Chicago, IL, 60615

Great! No complaints. Will be scheduling again soon. My cats loved her and she followed instructions exactly.

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Chevonne C.
Sitter Profile Image: Mia L.
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Mia L.
from
$18
per visit
5.0 out of 5 stars
26 reviews
5 repeat clients
3 years of experience
Hyde Park, Chicago, IL, 60615

Mia was incredible with my cat Stormie! We were able to quickly schedule a meet and greet for her to meet Stormie and I could already tell she genuinely cared. She asked questions about feeding, whether Stormie likes to sleep in the bed, daily routine, and took notes when I explained some food changes due to Stormie's sensitive stomach. It is VERY clear she does truly love and care for animals. We had Mia watch Stormie for the weekend and came back to the apartment being clean, litterboxes were empty and freshly cleaned, etc. Mia sent regular updates as well with photos and videos of Stormie so I knew that everything was going smoothly. She also sent messages regularly about how they were playing with toys, how Stormie was doing, etc. I 100% will book with Mia again as I truly never felt more comfortable with someone watching my baby before now.

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Lillian W.
Sitter Profile Image: Cassandra H.
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Cassandra H.
from
$14
per visit
5.0 out of 5 stars
69 reviews
25 repeat clients
25 years of experience
Hyde Park, Chicago, IL, 60615

Cassie is amazing at what she does and she is very professional and warm. She took great care of our cat and our home. She was always punctual and always sent wonderful notes and pictures. We would happily choose her again to take care of our cat.

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Sud R.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
248 reviews
86 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

As of now I have an aging cat which presents considerable challenges. Tamara was able to provide good care for her as I was away. She has visited my place many times throughout the year and I highly recommend her for all pet care needs. -William

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William P.
Sitter Profile Image: Simone B.
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Simone B.
from
$23
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
23 years of experience
Chicago, IL, 60615

Simone is absolutely amazing! She did a drop in before our first visit, which we know is extra work and she didn’t mind at all to take care of our sweet puppy who’s 4 months old. She didn’t mind the zoomies and I’m sure was so patient and playful with our pup we are absolutely booking a drop in again!

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Dana W.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$27
per visit
5.0 out of 5 stars
30 reviews
8 repeat clients
22 years of experience
Douglas, Chicago, IL, 60609

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

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Lillian & Jason A.
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Perfect for high energy dogs - Grand Boulevard

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

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Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
372 reviews
175 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Elizabeth was a pleasure to deal with from first contact until we picked Tika up at the end of the night. Amazing communication and pictures.

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David B.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$45
per day
5.0 out of 5 stars
132 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was absolutely fabulous with my boy! Took him for a nice long walk. I could tell when I picked him up that he had really bonded with her.

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Isabel C.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$40
per day
4.9 out of 5 stars
248 reviews
86 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

I was looking for daycare for my dog and am happy to have found Tamara! She’s great with communication and has been flexible which has been very helpful. And my dogs tail is always wagging when we walk up.

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Jennifer C.
Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Star Sitter
from
$48
per day
5.0 out of 5 stars
181 reviews
47 repeat clients
11 years of experience
Near South Side, Chicago, IL, 60605

Katrina is a fantastic dogsitter. Very kind, caring, and communicative. Very attentive to our senior dog who has separation anxiety and veterinary issues.

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Eric and Breanna S.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$30
per day
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

About: What sets me aside from other sitters is the love i have for animals. Since i was a little girl I've always loved being around animals they were and still are very therapeutic to me. I've had big dogs from Pitbull's, Dobermann, American bullies, all the way down to tiny dogs; yorkies, shitzu etc. even different kinds of cats you name it. As I've gotten older I've gained sooo much experience to the point I've had at home births with my dogs and cats all by myself; even home training my own animals as well. My goal here is to gain a work related reputation where i can truly start doing what i love and make a name for myself until i can become that super Veterinarian I've always dreamed of being. So far all i have is personal experience with dealing with animals at home and at my job(My residents animals). This would truly mean a lot if i can show off my skills and how genuine i am with animals and even people. Pet Care currently fits for me during the week days. I work doubles every Saturday and Sunday; whereas for school i do online Vet courses which is self pace. Which means i am free during the week Monday-Friday between 9am-5pm if communicated at least at least 30min-1hr in advanced i could stay later if needed. Although, I am a mother which means i can not do any services past 7pm nor any over night services. I also am located downtown Chicago but I am willing to travel!! One thing about me i will spoil your baby(s) haha; I am very hands on and affectionate with animals unless they require space lol. I have never been a crate animal person BUT i know every household is different and every animal requires different training. Again, animals bring a lot of joy to my heart; very therapeutic for me and if given the chance you wouldn't be disappointed i promise!.

Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter
from
$45
per day
5.0 out of 5 stars
128 reviews
57 repeat clients
23 years of experience
Hyde Park, Chicago, IL, 60615

Ashley takes great care of our puppy. Her kids give ample play time to entertain our puppy, and Ashley walks and feeds her well. She also is quick to respond to queries. Our puppy gets excited whenever coming to Ashley’s place.

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Smaida M.
Sitter Profile Image: Gabriel V.
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Gabriel V.
from
$33
per day
5.0 out of 5 stars
7 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: Timothy B.
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Timothy B.
Star Sitter
from
$40
per day
5.0 out of 5 stars
20 reviews
5 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: Ashley M.
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Ashley M.
Star Sitter
from
$42
per day
5.0 out of 5 stars
188 reviews
67 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley and her daughter Marina are incredibly conscientious and caring. Every time I bring my dog to their place, he is excited to run up the stairs and be reunited with his extended family. He truly loves them, and I can see how much they love him as well. 10/10, would recommend Ashley’s services to anyone!

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Eric R.
Sitter Profile Image: Monica M.
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Monica M.
from
$35
per day
5.0 out of 5 stars
13 reviews
5 repeat clients
19 years of experience
Bridgeport, Chicago, IL, 60608

About: Hi! My name is Monica and I recently graduated from Indiana University. I’ve grown up around animals my entire life, so caring for them has always come naturally to me. While I was in college, I fostered through local animal shelters, which gave me experience caring for animals with all different personalities, ages, and needs. I’m also currently a volunteer at the Anti-Cruelty Society in Chicago, where I help care for animals and support the shelter. I work from home, so I’m able to give pets a lot of attention throughout the day. Your pet will never be left alone for long. My dad is also recently retired and home most of the time, so there’s always someone around to give extra attention, playtime, and care. I have a small Yorkie named Tucker and a cat named Penny. They’re both very friendly and used to being around other animals. Tucker is great at matching other dogs’ energy (whether they want to play or relax), and Penny is very calm and tends to mind her own business. Whether it’s walks, playtime, feeding, or just keeping your pet company, I treat every animal like they’re part of the family. I’d love the opportunity to care for your pet and make sure they feel safe, happy, and comfortable while you’re away! I recently graduated from Indiana University and am now back home in Chicago full-time. My dad is retired and home all day, and I spend most of my time at home too, so your pet will always have company and attention. I’m not super busy and genuinely love being around animals — it’s the perfect setup! I have a private, fully fenced yard and never let pets outside without supervision. My home is spacious, and pets are welcome to relax anywhere they’d like. I also have a 2-year-old, 4.5-pound Yorkie who mostly keeps to himself but is always up for a little playtime if your pet wants a buddy! I’m happy to crate your dog at night if you prefer, or they’re welcome to sleep with me — I’d love that too!

Sitter Profile Image: David R.
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David R.
Star Sitter
from
$62
per day
5.0 out of 5 stars
388 reviews
94 repeat clients
10 years of experience
Loop, Chicago, IL, 60605

David and Jerrilyn are incredible! My puppy has never been happier— he gets friends at daycare and I got constant updates and pictures. As a first time dog owner it’s so nice having someone who can take care of my puppy and advise on any question I have on dog-care!

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Kinar P.
Sitter Profile Image: Brandon E.
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Brandon E.
from
$50
per day
5.0 out of 5 stars
21 reviews
11 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

About: Dawggy Pawties is a premium doggie daycare and enrichment retreat located in a peaceful rural setting designed specifically for city dog owners who want their dogs to experience freedom, exercise, fresh air, socialization, and structured care in a safe environment. The business includes pickup and drop-off transportation, outdoor play, socialization groups, nature walks, enrichment activities, and optional overnight boarding This is my full time job, so your pups will have my undivided attention!! My mornings start as early as 530 and end as late as 11 Your pooch will be with my family and I in our home as well as on our Farm that includes a private Dawg Pawk we also will visit different dog parks around the city of Chicago and trips to beach and other dog friendly places to provide proper socialization and public manners. your dawg will be provided with his/her own private crate to chill and relax during their stay!

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

About: ✦Limited spots left for Juneteenth and Father’s Day weekends • 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: Bola A.
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Bola A.
from
$49
per day
4.9 out of 5 stars
171 reviews
62 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Bola boarded my pup overnight and she was great. She's knowledgeable, loving and caring in her interaction with me and my fur buddy. We look forward to using her services again in the near future.

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Millicent C.
Sitter Profile Image: Jane C.
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Jane C.
from
$33
per day
5.0 out of 5 stars
1 review
10 years of experience
Hyde Park, Chicago, IL, 60615

About: I’ve cared for my sweet girl for about 10 years now. She’s changed over the years from a newly adopted young shelter dog to a senior dog and I’ve consistently modified how I care for her to meet her needs. I have boarded many family dogs too from tiny multi poms to larger sweet pits. I really feel at home with animals and treat every dog with patience and care like my own girl. I work from home, live across the street from a big park, and can offer plenty of walks, attention, and playtime. Please be sure to share If you’re dog requires supplements, medication, special feeding schedules/protocols, behavioral things I should be mindful of. I work from home Monday thru Friday. Typically up with my dog by 6. She gets a long walk in the am and after work. Plenty of walks in between work for potty breaks. Each day can look different though based on weather and overall energy level of your dog. I can adjust your dogs needs when it comes to feeding schedule, affection, attention, and stimulation. I vary my techniques based on your dog’s personality and what they need when it comes to affection, space and activity level. I am flexible!

Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per day
5.0 out of 5 stars
24 reviews
10 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

About: Looking for a dog sitter with a passion for pups and years of experience? I’ve not only been a dog mom for 14 years, but recently assisting in training the now 6 month old puppy that’s in my parent’s care. I’m the #1 dog sitter amongst my network, not only because I work from home and have availability, but because I also include their fur babies in my dog’s activities as well i.e. dog park dates, dog birthday parties, and doggie brunch! I’m a full- time remote employee with a very relaxed work schedule. Your pet will be spending the majority of their time in my care. I have a fenced front yard and a patio along with one 22lbs dog that will keep your pet company. I also have a lot of space to allow the dog to move around as they would like.

Sitter Profile Image: Morgan P.
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Morgan P.
from
$30
per day
5.0 out of 5 stars
19 reviews
3 repeat clients
14 years of experience
Grand Boulevard, Chicago, IL, 60653

Morgan was great! We needed someone to take care of our boy while we were at the White Sox game, and Morgan got back to us within minutes to let us know she was available. When we dropped him off she was immediately very engaging with Romeo and we could tell that she loves dogs and knows how to be around them. She did a great job watching him and I would recommend her to anyone!

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Chloe W.
Sitter Profile Image: Talla A.
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Talla A.
from
$40
per day
4.8 out of 5 stars
26 reviews
11 repeat clients
3 years of experience
Douglas, Chicago, IL, 60616

Excellent communication and clearly responsible. My dog was happy to meet her when I went to leave her a second time. Would strongly recommend.

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Soorya S.
Sitter Profile Image: Kyle H.
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Kyle H.
from
$40
per day
5.0 out of 5 stars
28 reviews
6 repeat clients
22 years of experience
Hyde Park, Chicago, IL, 60615

About: Kyle and Ben have been caring for dogs in our home for over fifteen years. We have experience administering medications, whether they be topical, ingested or intravenous. Our goal is to make sure you know your dog is safe and well cared for while you're out of town. We are very quick to respond to all phone calls, text messages and emails and will keep you posted with photos and updates on how your dog is doing while they are staying with us. We also provide flexible pick up and drop off hours for your convenience and can provide transportation if necessary. Kyle has several years of experience working in the pet care industry, starting with shelter work, moving onto a dog daycare/boarding facility and managing of two different dog and cat supply stores (one local, one corporate) in the last fifteen years. She is certified in dog and cat first aid and CPR by the American Red Cross and has experience administering topical, oral and intravenous medications. She has extensive experience handling senior and disabled animals, as well as dogs with behavioral issues. We have always loved dogs and owned dogs throughout our respective childhoods, but Kyle has gotten more hands on experience in the last fifteen years by dabbling in different fields of animal care. She worked as a kennel attendant at the local SPCA for a period of time, caring for homeless dogs, cats and rabbits. It was there that she learned proper care techniques and how to administer medications. She took these skills with her when she went to work first as a kennel attendant and then as the office manager of a small dog daycare and boarding facility. She spent the next seven years serving as store manager of two different natural dog and cat supply stores, where she helped pet owners provide their animals with healthy natural foods, treats and other supplies. She also organized many in store events to help highlight and raise funds for many local rescues and shelters. In 2020, Kyle completed school to become a dog groomer and has been grooming dogs in Hyde Park for the last several years. Both Kyle and Ben work mainly from home, or not far from home. Kyle works as a dog groomer and is able to bring your dog to work with her during the day to minimize any time your dog may spend without human supervision. We never allow anyone off leash on walks, and we do not utilize off leash dog parks for safety reasons. All of our pets are fully vaccinated. Feeding times are always supervised to prevent any potential food aggression. Toys and chews are put away when human supervision is unavailable to prevent resource guarding.

Sitter Profile Image: Torin I.
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Torin I.
from
$43
per day
5.0 out of 5 stars
23 reviews
8 repeat clients
13 years of experience
Grand Boulevard, Chicago, IL, 60615

About: Hi! It's been a pleasure watching so many amazing furry friends over the years here on Rover. I recently got a little buddy myself, so I am focusing on caring for her. If you're a repeat client (I have watched your pet before) feel free to send me a message and I'll see what I can do! Thanks :) currently working week day evenings and some Sundays, but my schedule varies a lot. Feel free to check with me and I’ll let you know what it looks like! My home is completely dog-safe. They won't be able to get into any trouble whether or not I'm around. I think body language is extremely important and I have a knack for figuring out what a dog may be wanting.

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More than 1.6 million
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Adventure-ready dog walkers - Grand Boulevard

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: Chelsea G.
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Chelsea G.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

About: What sets me aside from other sitters is the love i have for animals. Since i was a little girl I've always loved being around animals they were and still are very therapeutic to me. I've had big dogs from Pitbull's, Dobermann, American bullies, all the way down to tiny dogs; yorkies, shitzu etc. even different kinds of cats you name it. As I've gotten older I've gained sooo much experience to the point I've had at home births with my dogs and cats all by myself; even home training my own animals as well. My goal here is to gain a work related reputation where i can truly start doing what i love and make a name for myself until i can become that super Veterinarian I've always dreamed of being. So far all i have is personal experience with dealing with animals at home and at my job(My residents animals). This would truly mean a lot if i can show off my skills and how genuine i am with animals and even people. Pet Care currently fits for me during the week days. I work doubles every Saturday and Sunday; whereas for school i do online Vet courses which is self pace. Which means i am free during the week Monday-Friday between 9am-5pm if communicated at least at least 30min-1hr in advanced i could stay later if needed. Although, I am a mother which means i can not do any services past 7pm nor any over night services. I also am located downtown Chicago but I am willing to travel!! One thing about me i will spoil your baby(s) haha; I am very hands on and affectionate with animals unless they require space lol. I have never been a crate animal person BUT i know every household is different and every animal requires different training. Again, animals bring a lot of joy to my heart; very therapeutic for me and if given the chance you wouldn't be disappointed i promise!.

Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
248 reviews
86 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Twix loves her so much! He knows her car at this point and is jumping for us to let him go with his friend. She is so amazing withy doodle who isn’t the easiest to walk cause he is a puller and she does perfect with him. I have also used her for boarding and day care and I know when he is with her he is so happy and well taken care of ♥️

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Rania A.
Sitter Profile Image: Amiyah W.
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Amiyah W.
from
$10
per walk
3 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

About: I've had pets since I was 9. From 9 till now I've had cats, dogs, fishes, and guinea pigs. I have experience with dealing with pets that may have previously trauma issues also with pets that may need careful care like medince or special needs. Even pets that don't need extra care just pets that wants to have long walks or need a lot of play time . I am currently in school. So I will be working part time for Rover. Evening and nights works best for the weekdays and for the weekends I am open for anytime you need. For cats do have multiple cat bags if they need to brought to a appointment or any where else. And foot dogs if you don't have a leach I can get one but I would prefer for you to have leeches and rates of pets need to be taken out of the house .

Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$25
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

About: I’ve loved animals since I was a kid. My many years of pet ownership has trained me for this opportunity. My Chewy is both happy and healthy. I’m recently retired. My daily schedule is built around the needs of my boy, Chewy. He’s walked at minimum three (3) times a day; my friends and family know the routine. I have a secure deck to allow fresh air and free movement with guaranteed security. I have a crate if needed, but think all dogs should have free movement daily.

Sitter Profile Image: Brianna B.
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Brianna B.
from
$12
per walk
5.0 out of 5 stars
6 reviews
4 years of experience
Hyde Park, Chicago, IL, 60615

Excellent dog walker. She is dependable, trustworthy, and amazing with my dog. I felt completely comfortable leaving my pet in her care during my vacation. She responds is a great timely manner

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Lashemia B.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
82 reviews
33 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Q was great with Remi! She showed up ready to walk him and was prepared with any questions she had.

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Abi S.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$18
per walk
5.0 out of 5 stars
30 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

About: While I do not currently share my life with a dog of my own (it's a matter of being unable to adopt every dog I lay my eyes on!), I dearly love helping pet parents keep their dogs happy and healthy and preferably in their own homes while their owners are away. I love to travel,and love to spend time with as many dogs as I can possibly fit into my day. You can often find me chatting with others about their animals, and I am always interested in hearing about every little detail. I enjoy helping people get a greater understanding regarding the welfare of their animals, and sometimes bore my friends with random and obscure dog breeds, and what I know of their temperament and behavior. I'm proud to say I try to research as many breeds as I can so that I know what to expect, and hey, it's always fun to just know why and how a breed came into existence! I happen to also be studying veterinary technology, for the knowledge of nutrition and behavior, since surgery is more information than I want. :D I am also very happy to drop by or stay with your cats, and am quite used to the varying personalities of these small creatures: the ones who like to play hide and seek, the aloof, the playful, and the grumpy. I don't mind at all, as long as the cat is comfortable, eating, and using their litter box, all is well! I can work my day around your dog or cat, as I am a dedicated sitter, and much prefer to spend my time enjoying the company of cats and dogs as much as I can. I much prefer to stay with the dog or cat in their own home, as having their familiar surroundings help them remain peaceful, happy, and comfortable.

Sitter Profile Image: Manuela G.
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Manuela G.
from
$23
per walk
5.0 out of 5 stars
26 reviews
8 repeat clients
20 years of experience
Woodlawn, Chicago, 60637

Manuela did a great job! My dog Ella really enjoyed walking with her. Manuela is punctual, reliable. My dog doesn't trust people easily but with Manuela, it was easy. Amazing! Thank you so much. ?

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Sue K.
Sitter Profile Image: Mariam A.
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Mariam A.
from
$14
per walk
5.0 out of 5 stars
26 reviews
8 repeat clients
4 years of experience
Bridgeport, Chicago, IL, 60608

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: Julia G.
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Julia G.
from
$14
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
6 years of experience
Hyde Park, Chicago, IL, 60614

About: Hello!! My name is Julia I’m 23 and I love animals. Ever since I was little I’ve always had a special interest in nature and animas especially cats! One of my favorite childhood memories is rescuing feral kittens in my neighborhood and finding homes for them. In my teens years I started dog and cat sitting for friends and family and ever cared for horses and rabbits in my high schools FFA. As of now I’m a painter and artist with a lot of time on my hands and would love to spend some quality time with your pets! When staying with a pet I like to follow a schedule for potty and feeding times since familiar routines can calm pets that might be anxious around new people :)

Sitter Profile Image: Veronica M.
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Veronica M.
from
$15
per walk
4 years of experience
Chicago, IL, 60653

About: I love taking care of pets (mostly cats)! I will make sure your pet has been walked (for dogs) playtime, a clean litter box (for cats), and the proper food to make sure they're healthy. I'm currently working full time, but I have plenty of time in the evenings for your pet! I'm available after 5pm during the week and after 12pm on Saturdays. For in-home services, I make sure to follow all the directions the owner gives me. I also will clean up and alert the owner if their pet has an accident or throws up in their home.

Sitter Profile Image: Simone B.
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Simone B.
from
$25
per walk
5.0 out of 5 stars
10 reviews
3 repeat clients
23 years of experience
Chicago, IL, 60615

Simone was very prompt everyday for the week she walked my dog Fred. Most importantly, she was very kind a d Fred adored her. He already misses her!

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Tiffany P.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per walk
4.7 out of 5 stars
12 reviews
6 repeat clients
10 years of experience
Chicago, IL, 60653

Consistent, punctual, communicative, and generous. She shows up everyday in a timely manner, cares for my dog, and even gives complementary baths and cleaning if she makes a mess. HIGHLY RECOMMENDED 🤗 she offers a good range of services as well!!

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Nyla S.
Sitter Profile Image: Lillian M.
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Lillian M.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
24 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: Shannon T.
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Shannon T.
from
$20
per walk
10 years of experience
Kenwood, Chicago, IL, 60615

About: I have long-time experience caring for cats, and have cared for them most of my life. I am also experienced with dogs; I work part-time at a dog daycare doing pet transportation, boarding, and watching the daycare, which includes walks, feeding, playtime, and medication administration. I am detail oriented and always put the pet's comfort as a top priority. I am currently between full time employment and graduate school, meaning my days are completely flexible. I can come as early as 7am and as late as 10pm. I take entering people's homes seriously and want to leave the space better than how I found it. I will bring some of my own supplies to increase bonding with the dog or cat.

Sitter Profile Image: Morgan P.
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Morgan P.
from
$16
per walk
5.0 out of 5 stars
19 reviews
3 repeat clients
14 years of experience
Grand Boulevard, Chicago, IL, 60653

Morgan does a great job with my pup. Very professional and my dog loves her.

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Michelle R.
Sitter Profile Image: Jaden K.
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Jaden K.
from
$20
per walk
7 years of experience
Grand Boulevard, Chicago, IL, 60615

About: I’ve been caring for dogs of all kinds since I was around 10 years old, and for the past year I’ve consistently dog walked and dog sat for multiple families. I’ve also had my own dog for 7 years, so I understand the daily care, attention, and responsibility pets need. I’m comfortable with different breeds, sizes, and temperaments, and I always make sure each dog gets the exercise, routine, and care they deserve. Whether it’s long walks, feeding, or just keeping them company, I treat every pet like my own and make sure they feel safe and happy while you’re away. I’m a part-time dog walker and student, looking to fill my summer with wagging tails, fresh air, and more furry adventures! I have lots of free time during the week, so I’m very flexible. The pet’s safety and comfort are my top priorities. I always follow any given instructions and take time to build trust with every pet. I keep their water fresh, clean up any messes, and make sure pets feel safe, happy, and comfortable at all times.

Sitter Profile Image: Valeria V.
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Valeria V.
from
$18
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Val is great with our old soul! She is punctual, leaves great notes, and our dog looks forward to time with her.

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Allecia H.
Sitter Profile Image: Torin I.
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Torin I.
from
$25
per walk
5.0 out of 5 stars
23 reviews
8 repeat clients
13 years of experience
Grand Boulevard, Chicago, IL, 60615

About: Hi! It's been a pleasure watching so many amazing furry friends over the years here on Rover. I recently got a little buddy myself, so I am focusing on caring for her. If you're a repeat client (I have watched your pet before) feel free to send me a message and I'll see what I can do! Thanks :) currently working week day evenings and some Sundays, but my schedule varies a lot. Feel free to check with me and I’ll let you know what it looks like! My home is completely dog-safe. They won't be able to get into any trouble whether or not I'm around. I think body language is extremely important and I have a knack for figuring out what a dog may be wanting.

Sitter Profile Image: Masheika S.
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Masheika S.
from
$35
per walk
5.0 out of 5 stars
72 reviews
23 repeat clients
7 years of experience
Chicago, IL, 60653

Masheika is wonderful! She’s communicative and pays attention to detail. She’s very good with our anxious, scared dog, and Masheika has proven to be very patient and willing to work with her.

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Kaitlyn B.
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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 - Grand Boulevard

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: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
20 reviews
5 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
372 reviews
175 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Liz and her family were so good to Tyson. He loved staying there, and they really welcomed him into their family. He's the kind of dog who thrives off of attention and love, and they gave him plenty of both. I also got great updates and pictures which really made me feel like he was in good hands. I will definitely book with them again, if possible!

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Mallika T.
Sitter Profile Image: Jenna M.
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Jenna M.
from
$53
per night
5.0 out of 5 stars
93 reviews
22 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

Jenna was absolutely amazing! I felt so reassured with the pictures and videos and updates that our dog was safe, cared for, and having the nicest time! Jenna went above and beyond when our flight home was delayed and was so generous in accommodating us. Thank you Jenna! 😊

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Sarah W.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was a wonderful sitter! My dog was well cared for and had a blast. I will book with her again !

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Michelle C.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
248 reviews
86 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Tamara was absolutely amazing with Frankie! From the moment I dropped her off, I could tell she was in safe, caring hands. She kept me updated with regular messages and photos, which really put my mind at ease while I was away. It’s clear she truly loves and understands dogs, and Frankie seemed so happy and comfortable in her care. I couldn’t have asked for a better experience, and I’ll definitely be booking with her again!

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Yahya M.
Sitter Profile Image: Fortino V.
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Fortino V.
Star Sitter
from
$41
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
5 years of experience
West Town, Chicago, IL, 60642

Fortino was amazing! My dog is pretty high energy and I could tell he was having a great time. Fortino sent regular updates and he took my dog on lots of fun excursions with his own dog. He was very communicative and I could tell he paid close attention to details of my dog’s comfort, personality, etc. He even gave my dog a sweater that previously belonged to his dog but was too small, which was very sweet. Will definitely board with him again.

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Andrea S.
Sitter Profile Image: Tonisa J.
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Tonisa J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
80 reviews
37 repeat clients
15 years of experience
Calumet Heights, chicago, IL, 60617

Tonisa was great!! We did a meet and greet first. She was accommodating of any special needs and took care of Rocky like her own! Great with pictures and videos too! Rocky will be back to see Ava, his new friend.

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Jeanine R.
Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$57
per night
5.0 out of 5 stars
35 reviews
15 repeat clients
50 years of experience
Near North Side, Chicago, IL, 60611

Steven was very communicative during pickup and drop off. He shared regular updates and photos of Polo that put us in peace of mind. Polo had a very nice and comfy stay with Steven. And I’d recommend Steven to anyone who is looking for a pet sitter in the area.

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Akshay A.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
188 reviews
67 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley is AMAZING with our dog Rue! She sends such sweet photos and updates, she’s flexible and responsive - we always know Rue is in great hands when we’re out of town.

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Maya H.
Sitter Profile Image: Sara T.
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Sara T.
from
$40
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Lower West Side, Chicago, IL, 60608

I had a great experience with Sara. She communicated well and was really easy going. She sent pictures and videos. And our dog Boomer seemed to have a great time! I would happily book again!

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Carly R.
Sitter Profile Image: Nathan D.
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Nathan D.
Star Sitter
from
$57
per night
5.0 out of 5 stars
188 reviews
69 repeat clients
22 years of experience
Near North Side, Chicago, IL, 60654

Nathan was amazing! I was sorry worried about leaving Ollie bear for the first time but he was so responsive and sent tons of pictures! I felt so good knowing Ollie was so well taken care of.

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Kristi J.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$60
per night
5.0 out of 5 stars
99 reviews
30 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni took great care of my buddy! She sent regular updates and pictures. I knew he was in great hands which made it much easier to be away. Bunk looks forward to his next visit!

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Rebecca R.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$50
per night
4.9 out of 5 stars
52 reviews
10 repeat clients
21 years of experience
Bridgeport, Chicago, IL, 60616

Sarah B was so nice and accommodating. This is the first time my pet has stayed with a sitter and my mind was completely at ease. Thanks Sarah!

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Anne S.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
132 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania is amazing! She’s checked in with pix and videos daily. My pup came home so happy and content. I’ll definitely be checking her schedule the next time I need a sitter. 10/10 ☺️

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

Christina was phenomenal! She gave regular updates and checked in when Lola had an upset stomach, but what says it all is how comfortable and relaxed Lola was when I picked her up! You can just tell when your pup is in good hands, you know? We will definitely use Christina again!

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Stephanie G.
Sitter Profile Image: Iwona K.
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Iwona K.
from
$50
per night
5.0 out of 5 stars
597 reviews
194 repeat clients
22 years of experience
West Town, Chicago, IL, 60622

Iwona is amazing! It felt so comfortable to leave our Phoebe with Iwona - she immediately understood what is important for Phoebe, she carefully listened to us to be able to provide the routine our little doggy is used to. She sent Phoebe’s pictures every day to us with the text of how Phoebe felt. It’s so important to have a person you can trust with your little baby, and I am so happy we met Iwona.

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Maria S.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
360 reviews
98 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

Katie was great! Chloe seemed like she had a fun time with her. Katie sent lots of pictures! We also were really grateful for how accommodating Katie was - our flight was delayed and she was so nice about us having to switch around pickup plans.

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Maggie S.
Sitter Profile Image: Brandon E.
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Brandon E.
from
$42
per night
5.0 out of 5 stars
21 reviews
11 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

Brandon was awesome to work with! He kept consistent with his communication and took care of our fur baby. He’s also a trainer, so your pup is in good hands!

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Derrick V.
Sitter Profile Image: Bola A.
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Bola A.
from
$54
per night
4.9 out of 5 stars
171 reviews
62 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Bola took great care of my pup child. Rhea received lots of love and was definitely spoiled. (I can tell) lol Bola was responsive and sent updates and videos of Rhea. Rhea really likes Bryce and I hope they become long-term pup friends. I would definitely book again without giving it a second thought.

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Nicole M.
Sitter Profile Image: Angel V.
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Angel V.
Star Sitter
from
$47
per night
5.0 out of 5 stars
106 reviews
29 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.
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