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.

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

“Thankful. Very positive and seamless experience. My sitter cancelled last minute and I reached out to E K. And within minutes we set up an appointment to meet my pup. After, she gave me a set of instructions for the morning and everything went smoothly. As a firefighter, family is everything to me and Pongo is my comfort dog. To know he was taken care of through out the day made my stressful shift easier to navigate. I strongly recommend E K. To anyone. Large home. Back yard. And positive vibes. Thank you again.”

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Robert R.
Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
• 188 reviews
75 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

“She was fantastic and so helpful. Best with pics and updates. Thank you for taking care of my boy. Will definitely be letting my man stay with you again.”

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Henry A.
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
• 39 reviews
25 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

“Kamiah and Casius were great sitters for Bailey. For me, it was a very last minute booking and Kamiah was incredibly accommodating to make it work. She was also very quick to contact us on the first day when Bailey wasn't eating (but everything was fine, as this is how Bailey always is at a new place), and Bailey looked very happy in the photos and videos we got each day. Also, Kamiah's pick-up and drop-off were prompt and efficient. I definitely plan to use them again!”

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Kurt S.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$40
per night
5.0 out of 5 stars
• 10 reviews
3 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: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 31 reviews
13 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: Ann V.
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Ann V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 144 reviews
30 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60605

“Ann did an excellent job dogsitting. She communicates effectively and thoroughly. She sent updates and pictures. Drop-off and pick-up was smooth. Classy was so happy after his visit. Thank you, Ann.”

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

“Ashley was great! She sent lots of updates and helped reassure me that my little girl was in good hands. She was very considerate and only accepted additional bookings for dogs that she thought would get along well with my pup. Overall, I was very impressed with Ashley and would highly recommend!”

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Madison D.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 151 reviews
7 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: Jessica G.
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Jessica G.
from
$45
per night
5.0 out of 5 stars
• 13 reviews
5 repeat clients
10 years of experience
New City, chicago, IL, 60609

“Krypto enjoyed a lot at Jessica's place. She was very kind enough to send so many pics of krypto and she took good care of him. Will recommend her for everyone.”

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Sunitha B.
Sitter Profile Image: Ebonee A.
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Ebonee A.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 50 reviews
23 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

“Ebony was amazing with Jessica. She made sure we got updates with her and videos. Jessica really loved her and her family. I will definitely be booking future dates with her from now on. Thank you Ebonee for being so gentle and kind to our lovely Jessica.”

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Alicia H.
Sitter Profile Image: Lashonda S.
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Lashonda S.
from
$40
per night
5 years of experience
Grand Boulevard, Chicago, IL, 60653

About: I have 4 years of experience caring for dogs and absolutely love animals. I’m comfortable with puppies, small dogs, feeding schedules, walks, playtime, crate routines, and puppy-pad care. I understand how important it is to have someone you can trust with your pet, so I’ll treat your fur baby with the same love, patience, and attention I give my own. I’m also happy to provide regular pictures and updates so you can feel comfortable while you’re away. I have a flexible schedule that allows me to provide attentive and reliable pet care. I’m available throughout the week and on weekends and can accommodate walks, drop-ins, and overnight care depending on your pet’s needs. Your pet’s safety and comfort are my priority. I provide a clean, comfortable environment with plenty of attention, playtime, and supervision. I follow each pet parent’s feeding, walking, and care instructions closely and provide updates while your pet is in my care.

Sitter Profile Image: Patrick & Susan C.
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Patrick & Susan C.
from
$55
per night
5.0 out of 5 stars
• 5 reviews
3 repeat clients
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: Jenna M.
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Jenna M.
Star Sitter
from
$53
per night
5.0 out of 5 stars
• 103 reviews
24 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

“Great as always. Had a personal emergency pop up and she was so easy to work with around it. Your animals will always be in great hands with her.”

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J.T. A.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.9 out of 5 stars
• 30 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: Kyla & Barbara G.
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Kyla & Barbara G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 76 reviews
30 repeat clients
20 years of experience
West Elsdon, Chicago, IL, 60632

“Kyla was incredible!! From the initial contact to pickup, she was friendly and professional. She took the time to know my dog’s needs and preferences. She sent me regular updates and photos of my pup, which put me at ease while I was away! I highly recommend Kyla for a trustworthy and caring place for their dog. I’ll definitely be booking again!”

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Agnes K.
Sitter Profile Image: Niamh M.
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Niamh M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 19 reviews
2 repeat clients
10 years of experience
Near North Side, Chicago, IL, 60610

“Niamh was the sweetest with my pup! I last minute needed to bring him on a work trip to Chicago and she instantly put me at ease, knowing we wouldn't be able to do a meet n greet beforehand. From the video call, to dropping him off, Niamh was very communicative and provided updates throughout the day. Highly recommend her if you are in the Chicago area or traveling with your pet and need someone reliable to watch them!”

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

“Ksenia took fantastic care of our dog Alfie! She was super attentive to him and sent us lots of updates during his stay. He also got along really well with her pup! Would definitely board Ksenia again!”

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Christiana L.
Sitter Profile Image: Kathleen K.
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Kathleen K.
Star Sitter
from
$48
per night
5.0 out of 5 stars
• 11 reviews
6 repeat clients
3 years of experience
Evergreen Park, IL, 60805

“Nemo took to Kathleen right away. She kept him busy with walking and playing with her children. She is a dog lover! He is as in good hands. Sent several pics too. Would definitely ask her to sit again.”

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Linda B.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
• 278 reviews
99 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

“Tamara was great, just like last time. She provided updates, pics and I really feel calm that my Nina is being cared and loved. Highly recommend.”

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Daniella V.
Sitter Profile Image: Thomas Q.
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Thomas Q.
from
$30
per night
5.0 out of 5 stars
• 4 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.
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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 - Grand Boulevard

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: Maia S.
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Maia S.
from
$14
per visit
5.0 out of 5 stars
• 15 reviews
2 repeat clients
4 years of experience
Chicago, IL, 60653

“Maia is the most kind and thoughtful cat sitter! She took care of our little Brinkis so well! She shared regular updates, took such lovely care of our home, and is an overall loving and warm person. She went above and beyond to care for our little baby. Would highly recommend!”

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Joanna A.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
• 92 reviews
35 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: Ruari H.
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Ruari H.
from
$9
per visit
5.0 out of 5 stars
• 9 reviews
5 repeat clients
5 years of experience
Bridgeport, Chicago, IL, 60608

“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: Christina D.
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Christina D.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 15 reviews
5 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: Tamara J.
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Tamara J.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
• 278 reviews
99 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: Evan P.
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Evan P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 58 reviews
17 repeat clients
30 years of experience
Hyde Park, Chicago, IL, 60615

“Evan did a wonderful job watching our cat for a long weekend. He was communicative and responsive, which made us feel comfortable and confident that our cat was in great hands.”

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Anna B.
Sitter Profile Image: Syenna M.
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Syenna M.
from
$14
per visit
5.0 out of 5 stars
• 5 reviews
3 repeat clients
8 years of experience
Hyde Park, Chicago, IL, 60615

About: I have experience caring for both energetic dogs who need structure and movement, as well as more sensitive pets who benefit from patience, gentle routines, and clear communication. I’m organized, responsive, and great at managing schedules—skills I use every day in my professional work and bring directly into pet care. I pay attention to details, follow instructions carefully, and make sure owners feel fully informed while they’re away. I’m a reliable and attentive weekend pet sitter based in Boston, and I take pride in creating a calm, safe, and caring environment for every animal I look after. I work a full-time remote job during the week, but on weekends I’m fully dedicated to pet care—whether that means long walks, dedicated playtime, or simply keeping your pet company and relaxed at home. As someone who values consistency and trust, I make sure every pet gets thoughtful, individualized attention. Whether your pet needs slow, steady walks, a playful activities, or lots of affection, I’m here to help your weekend feel stress-free. If you’re looking for a sitter who is responsible, communicative, and truly loves spending her weekends with animals, I’d love to support you and your pet!

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

“Jasmine was great, I really appreciated her willingness to come over for a meet and greet before sitting. Thanks for letting Mickey lick the spoon! 🐈😹”

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Danielle W.
Sitter Profile Image: Cathalina A.
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Cathalina A.
from
$16
per visit
5.0 out of 5 stars
• 1 review
15 years of experience
Chicago, IL, 60653

“Cathalina was perfect, did daily check ins while I was out of town ! Sent pictures to update us everyday while I was away missing my pup! 10/10 would rebook cathalina again !!”

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Areanna M.
Sitter Profile Image: Brianna M.
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Brianna M.
from
$18
per visit
5.0 out of 5 stars
• 2 reviews
1 year of experience
Grand Boulevard, Chicago, IL, 60653

About: I love puppies and letting them get socialized! I have a 5 month old puppy myself and choosing me to watch your baby would be an honor! I work from home so your pup will never be alone! I work from home all day! My puppy goes with me almost everywhere and I frequently take walks so your puppy would be in great hands I have a fenced yard as well as a big open play pen for my puppy and plenty of toys for your pup to play with!

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

“Nadine was wonderful! She took great care of my cat, followed all feeding instructions perfectly, and sent great updates. It gave me total peace of mind knowing my cat was in good hands. Thanks so much!”

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Yacine B.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per visit
4.8 out of 5 stars
• 13 reviews
8 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: Huibo L.
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Huibo L.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
4 repeat clients
8 years of experience
Chicago, IL, 60615

“The best summaries I’ve ever received from a pet sitter here on Rover. Will definitely book again with Huibo in the future!!”

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Dominique L.
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

“This is my second time booking a stay with Sally, and I really can’t say enough wonderful things about her. I left her with two (somewhat shy) kittens for two weeks, and they must have remembered her from her first visit because it didn’t take very long for them to warm up and soak up all the love. I haven’t seen them as affectionate with anyone so far as they were with her. She’s so incredibly sweet to them I didn’t have a single worry being away for such an extended period of time. Her pictures also made me rest assured that they were having a blast. I came home to the happiest little guys and I can’t thank Sally enough. I would recommend booking with her in a heartbeat.”

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Morgan I.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
• 31 reviews
13 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

“Daphnay was very amenable to last minute plans she communicated well and sent photos!”

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Natala B.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
• 49 reviews
17 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: Taylor W.
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Taylor W.
from
$18
per visit
5.0 out of 5 stars
• 5 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: Kiera B.
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Kiera B.
from
$15
per visit
5.0 out of 5 stars
• 30 reviews
22 repeat clients
8 years of experience
Chicago, IL, 60615

“Kiera took great care of our cat and our home. She was communicative and developed a great bond with our cat, helping us to have a stress-free vacation. She left our home in good, clean condition after an 8-day home stay.”

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Claire A.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$27
per visit
5.0 out of 5 stars
• 32 reviews
9 repeat clients
22 years of experience
Douglas, Chicago, IL, 60609

“Elizabeth was amazing with my cat. This was my first time using a sitter I didnt know personally and she eased all of my fears. Multiple updates with pictures. Not to mention being great to work with- with a calming personality. Would definitely book her again.”

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Joy M.
Sitter Profile Image: Katharine M.
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Katharine M.
from
$18
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
15 years of experience
Chicago, IL, 60615

About: I have volunteered at animal shelters since I was 10 years old, and am comfortable with dogs and cats of all sizes and ages! Additionally, I have seven years of experience pet/house sitting, including overnight. In the past few years, I have specialized in caring for puppies, and have experience with bottle feeding. I also had the unique opportunity to work with a coalition that supported people experiencing domestic violence by connecting their pets with fosters while they stayed in shelters (which normally do not allow animals.) I am currently a grad student at the University of Chicago, and have quite a bit of flexibility in my schedule! Whether you would like me to stay at your home full-time while you are away, or just need me to stop by for periodic visits, walks, or play-time, I have plenty of time to dedicate to your pets! I am available both during the week and on the weekends, and can't wait to spend them hanging out with your cats and dogs! I am very comfortable walking dogs of all sizes, and am happy to take them outside to play as well! If your pet has any medication, I can make sure they take them. I will make sure that dogs have plenty of potty breaks, and that all animals are fed on time. If I am staying in your home, I will be respectful of any boundaries you have and will leave the place just as you left it.

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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.

1 / 1
Sitter Profile Image: E K.
Verified Background Check
E K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
• 397 reviews
185 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

“From the moment Teddy entered E. K's home it was like I didn't exist. Kind of like dropping off your kids at preschool and they don't say goodbye. Teddy had a great day with the other dogs especially Allie and will definitely be back.”

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Susan L.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$40
per day
4.9 out of 5 stars
• 278 reviews
99 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: Tamya O.
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Tamya O.
from
$40
per day
5.0 out of 5 stars
• 5 reviews
1 repeat client
4 years of experience
Grand Boulevard, Chicago, IL, 60653

“Having Tamya provide day care for our Weimaraner MacKenzie was the best decision! We traveled from the DC area to Chicago to visit the new Obama Presidential Library and Center and wanted to ensure she would be in good hands for the several hours we were away. Tamya made planning for MacKenzie very easy and I was impressed with the advanced questionnaire provided so that they could match the needs for her. They got along superbly. Thank you Tamya for caring for our little girl!”

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Donna H.
Sitter Profile Image: Bola A.
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Bola A.
from
$49
per day
4.9 out of 5 stars
• 188 reviews
75 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

“Bola came through for me last minute and took great care of Bea!! She sent me picture updates and communicated well throughout the day. Will definitely be booking again with her.”

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Abby B.
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 Thanksgiving• South Loop/Downtown• Bridgeport 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: Brianna M.
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Brianna M.
from
$35
per day
5.0 out of 5 stars
• 2 reviews
1 year of experience
Grand Boulevard, Chicago, IL, 60653

About: I love puppies and letting them get socialized! I have a 5 month old puppy myself and choosing me to watch your baby would be an honor! I work from home so your pup will never be alone! I work from home all day! My puppy goes with me almost everywhere and I frequently take walks so your puppy would be in great hands I have a fenced yard as well as a big open play pen for my puppy and plenty of toys for your pup to play with!

Sitter Profile Image: Gabriel V.
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Gabriel V.
from
$33
per day
5.0 out of 5 stars
• 9 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: Ashley M.
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Ashley M.
Star Sitter
from
$42
per day
5.0 out of 5 stars
• 210 reviews
75 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: Cori W.
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Cori W.
from
$45
per day
5.0 out of 5 stars
• 17 reviews
3 repeat clients
9 years of experience
Douglas, Chicago, IL, 60616

“Cori was Everything you could want in a dog sitter. I truly felt like she was excited to see my dog and take care of him as though he was her own. I got prompt and regular updates, and she was friendly and flexible, and puppy came back happy! She even gave him a toy as a gift because she said he liked it so much.”

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Eve E.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per day
5.0 out of 5 stars
• 31 reviews
13 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: Timothy B.
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Timothy B.
Star Sitter
from
$40
per day
4.9 out of 5 stars
• 30 reviews
8 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

“My wife and I used Timothy on a trip from Florida to Oshkosh. We were passing through and wanted to take my daughter to the field museum and the shed aquarium. We had our German Shepherd, Sheba, with us, we reached out to Timothy and he agreed to watch Sheba for the afternoon. Timothy went above and beyond. He met us on the steps of the museum to pick Sheba up, and brought her back to us. I cannot overstate how great the experience was, we highly recommend using Timothy. He is extremely nice and easy to deal with.”

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Yulia V.
Sitter Profile Image: Ebonee A.
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Ebonee A.
Star Sitter
from
$45
per day
5.0 out of 5 stars
• 50 reviews
23 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

“I can not say enough about Ebonee! She is totally amazing! She took such good care of Milo and sent pictures and videos of his stay with her. She is responsive and accommodating! I'm am more than pleased with her level of care.”

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Marquetta S.
Sitter Profile Image: Patrick & Susan C.
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Patrick & Susan C.
from
$40
per day
5.0 out of 5 stars
• 5 reviews
3 repeat clients
25 years of experience
Near South Side, Chicago, IL, 60605

“Patrick and Susan have been wonderful. This was the first time I’ve used a dog sitter before and They have put my mind at ease and I feel very confident that my dog is being taken care of. Thank you Patrick and Susan!”

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

“Thomas was great with Rey. I really appreciated how responsive he was. Thanks again!”

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Lindsay D.
Sitter Profile Image: Caitlin M.
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Caitlin M.
from
$40
per day
4.5 out of 5 stars
• 5 reviews
1 repeat client
30 years of experience
McKinley Park, Chicago, IL, 60609

About: I’ve taken care of or have had animals since I was a child. Currently I have a cat named Ida who is very sweet & affectionate. I always strive for a 5-star experience, but my top priority will always be the safety of the pets in my care. I chose to refuse a request to take a cat outside without a harness, as the flight risk was far too high. It resulted in a low rating, but I will never compromise an animal's safety. I just graduated with a Master’s of Social Work. Before beginning my career, I’m taking some down time and taking care of animals. This gives me the ability to prioritize your pets needs! My environment is animal friendly. I have a fenced in back yard and live near a park. I have a cat named Ida who is welcoming to new animals inside our home. I allow animals on my bed and furniture.

Sitter Profile Image: Vivian N.
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Vivian N.
from
$35
per day
5.0 out of 5 stars
• 13 reviews
9 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: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$55
per day
5.0 out of 5 stars
• 108 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: Talla A.
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Talla A.
from
$40
per day
4.8 out of 5 stars
• 27 reviews
11 repeat clients
3 years of experience
Douglas, Chicago, IL, 60616

“Talla was such a sweetheart. She took great care of Wilbur and made sure to update me regarding his activities and medications. She was available last minute and was very responsive and communicative!”

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Christina G.
Sitter Profile Image: Jennifer N.
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Jennifer N.
Star Sitter
from
$30
per day
4.9 out of 5 stars
• 286 reviews
129 repeat clients
6 years of experience
Lower West Side, Chicago, IL, 60608

“I’ve had dogs for 26 years and it’s very clear that Jennifer and her husband are highly experienced dog lovers. My boy came back to me with a very peaceful energy which tells me he was well cared for. Highly recommend them!”

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Isabel C.
Sitter Profile Image: Chent & Princess S.
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Chent & Princess S.
from
$40
per day
5.0 out of 5 stars
• 41 reviews
9 repeat clients
6 years of experience
Douglas, Chicago, IL, 60616

“Sweetest pet sitter ever! Our dog is people shy and he warmed up right away. You can really tell that princess cares for every animal she meets!! Definitely would rebook if in the area again!”

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

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: artiss m.
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artiss m.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 22 reviews
6 repeat clients
20 years of experience
Chicago, IL, 60615

“Artiss has walked my pup multiple times, and he has always been happy to see her! She has done a great job managing his high energy level, sent wonderful photo updates, and always made sure he went to the bathroom.”

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

“Tamara was so great and accommodating to my schedule! I was so happy with her communication with me and how she cared for my pups on their walk!”

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Tylena J.
Sitter Profile Image: Ruari H.
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Ruari H.
from
$10
per walk
5.0 out of 5 stars
• 9 reviews
5 repeat clients
6 years of experience
Bridgeport, Chicago, IL, 60608

About: i’m patient, detail-oriented, and genuinely enjoy getting to know each pet’s personality. i take the time to make shy or anxious pets feel safe and comfortable, and i adjust my approach depending on their energy level and needs. i’m also very reliable with routines and communication, so you can trust your pet is getting consistent care and attention. pet care is part of my everyday routine, as i currently care for two kittens with consistent feeding, cleaning, and play schedules. i’m used to planning my day around their needs, so incorporating additional pet care is something i can do reliably & consistently. when caring for pets in a client’s home, i focus on keeping their routine as consistent as possible. i follow all instructions closely, including feeding schedules, litter box cleaning, playtime, and any specific preferences your pet has. i take the time to understand each cat’s personality—whether they’re social or more independent—and adjust my approach so they feel comfortable in their own space. i also keep the home tidy and provide regular photo and message updates so you always know how your pet is doing.

Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 92 reviews
35 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: Syenna M.
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Syenna M.
from
$15
per walk
5.0 out of 5 stars
• 5 reviews
3 repeat clients
8 years of experience
Hyde Park, Chicago, IL, 60615

“Syenna was so responsive and wonderful with Ollie. We look forward to using her services again. Thank you!”

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Yulia G.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per walk
4.8 out of 5 stars
• 13 reviews
8 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: Brianna M.
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Brianna M.
from
$20
per walk
5.0 out of 5 stars
• 2 reviews
1 year of experience
Grand Boulevard, Chicago, IL, 60653

About: I love puppies and letting them get socialized! I have a 5 month old puppy myself and choosing me to watch your baby would be an honor! I work from home so your pup will never be alone! I work from home all day! My puppy goes with me almost everywhere and I frequently take walks so your puppy would be in great hands I have a fenced yard as well as a big open play pen for my puppy and plenty of toys for your pup to play with!

Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$18
per walk
5.0 out of 5 stars
• 32 reviews
9 repeat clients
20 years of experience
Chicago, IL, 60609

“Levi (Elizabeth) is an incredible sitter with my grumpy old dog! He’s a very difficult boy to work with and barks and barks at her, yet she is patient, kind, and gentle with him, meeting him on his terms. Highly, highly recommend!!”

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Tammy M.
Sitter Profile Image: Valeria V.
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Valeria V.
from
$16
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: Leah H.
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Leah H.
from
$17
per walk
4.8 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Grand Boulevard, Chicago, IL, 60653

About: I am a CPR certified pet sitter who loves animals and loves to care for things. I have no pets of my own because I travel often for my full-time job . However. , I look forward to building a trust worthy, healthy relationship with you and your animal family. I currently work from home full-time so I have flexible hours. I do travel often for work so the further out I know for overnight days is the better. I also am available to walk dogs daily. I live alone and a very nice neighborhood full of lots of trees and families. I keep a very neat and nice home free of anything that could harm animals.

Sitter Profile Image: Huibo L.
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Huibo L.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
• 3 reviews
4 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60615

“Amazing and very detailed walker! You won’t be disappointed 😇”

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luanda
Sitter Profile Image: Maia S.
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Maia S.
from
$17
per walk
5.0 out of 5 stars
• 15 reviews
2 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60637

About: I’ve grown up with animals all my life and my house was always noisy. However, now that I’ve moved away from home I’ve been missing the little guys. Im going into a my Masters program at UChicago! I’m also a barista at Starbucks! I usually work in the early morning so my afternoons are pretty open! I have the upmost respect for others property and place. I would love to board animals at my apartment if you are comfortable with it! However, I will come second to only you in loving your animal.

Sitter Profile Image: Erin M.
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Erin M.
from
$22
per walk
5.0 out of 5 stars
• 22 reviews
10 repeat clients
2 years of experience
Hyde Park, Chicago, IL, 60637

“Erin has been walking my dog Oscar every day and has been great to work with. She’s reliable, communicative, and clearly cares about Oscar and my two cats. Oscar is always happy after his walks, and I appreciate knowing he’s in good hands. Definitely recommend her to anyone looking for a trustworthy dog walker!”

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Brady P.
Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$19
per walk
5.0 out of 5 stars
• 38 reviews
19 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

“Jozelin took Leo on morning walks while I was out of town for a few days. She followed my instructions, was respectful of the space, & was able to handle my Leo. Will book again!! Tyyy”

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Cassidy C.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$26
per walk
5.0 out of 5 stars
• 49 reviews
17 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

“Chelsea is super patient and collaborative! She is dedicated to gaining my dog's trust as my dog's new and first ever walker.”

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Cory H.
Sitter Profile Image: Ava G.
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Ava G.
from
$15
per walk
13 years of experience
Bridgeport, Chicago, IL, 60609

About: What sets me apart is my experience caring for animals of all different ages and personalities. I’ve been taking care of animals since I was about 7 years old, and I’ve cared for cats and dogs. I’ve also had experience caring for senior pets, including looking after a 22-year-old cat while their owner was away. I’m patient, attentive, and comfortable adapting to each pet’s individual needs and routine. I understand how important it is for pets to feel safe, comfortable, and cared for while their owners are away. I'm currently taking my college classes online, so I have plenty of time to take care of animals! I am available pretty much every day of the week for whatever your pet needs. Having experience with reactive animals, I understand that comfort and familiarity are number one for a pets safety. I have no problem adapting to an animal's needs so that they can trust me and feel comfortable with my care, whether it be sitting patiently with them until they feel safe, or crating an animal if need be. My top priority is making sure your furbabies are fed, having fun, and not scared!

Sitter Profile Image: Kiera B.
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Kiera B.
from
$28
per walk
5.0 out of 5 stars
• 30 reviews
22 repeat clients
8 years of experience
Chicago, IL, 60615

“Kiera was absolutely wonderful! She was punctual and really good at communicating! Would definitely choose her again!”

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Gauri T.
Sitter Profile Image: Katharine M.
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Katharine M.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
2 repeat clients
15 years of experience
Chicago, IL, 60615

About: I have volunteered at animal shelters since I was 10 years old, and am comfortable with dogs and cats of all sizes and ages! Additionally, I have seven years of experience pet/house sitting, including overnight. In the past few years, I have specialized in caring for puppies, and have experience with bottle feeding. I also had the unique opportunity to work with a coalition that supported people experiencing domestic violence by connecting their pets with fosters while they stayed in shelters (which normally do not allow animals.) I am currently a grad student at the University of Chicago, and have quite a bit of flexibility in my schedule! Whether you would like me to stay at your home full-time while you are away, or just need me to stop by for periodic visits, walks, or play-time, I have plenty of time to dedicate to your pets! I am available both during the week and on the weekends, and can't wait to spend them hanging out with your cats and dogs! I am very comfortable walking dogs of all sizes, and am happy to take them outside to play as well! If your pet has any medication, I can make sure they take them. I will make sure that dogs have plenty of potty breaks, and that all animals are fed on time. If I am staying in your home, I will be respectful of any boundaries you have and will leave the place just as you left it.

Sitter Profile Image: Jenna M.
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Jenna M.
from
$21
per walk
5.0 out of 5 stars
• 48 reviews
20 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60608

“Jenna has been fantastic dog walker for Archer and I! She’s communicative, super responsive, and personable!! Highly recommend her to any pet owner!”

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Connor C.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$25
per walk
5.0 out of 5 stars
• 10 reviews
3 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.

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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.

1 / 1
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 397 reviews
185 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

“Thankful. Very positive and seamless experience. My sitter cancelled last minute and I reached out to E K. And within minutes we set up an appointment to meet my pup. After, she gave me a set of instructions for the morning and everything went smoothly. As a firefighter, family is everything to me and Pongo is my comfort dog. To know he was taken care of through out the day made my stressful shift easier to navigate. I strongly recommend E K. To anyone. Large home. Back yard. And positive vibes. Thank you again.”

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Robert R.
Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
• 188 reviews
75 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

“She was fantastic and so helpful. Best with pics and updates. Thank you for taking care of my boy. Will definitely be letting my man stay with you again.”

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

“Ashley was great! She sent lots of updates and helped reassure me that my little girl was in good hands. She was very considerate and only accepted additional bookings for dogs that she thought would get along well with my pup. Overall, I was very impressed with Ashley and would highly recommend!”

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Madison D.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 151 reviews
7 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
• 103 reviews
24 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

“Great as always. Had a personal emergency pop up and she was so easy to work with around it. Your animals will always be in great hands with her.”

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J.T. A.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.9 out of 5 stars
• 30 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: Niamh M.
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Niamh M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 19 reviews
2 repeat clients
10 years of experience
Near North Side, Chicago, IL, 60610

“Niamh was the sweetest with my pup! I last minute needed to bring him on a work trip to Chicago and she instantly put me at ease, knowing we wouldn't be able to do a meet n greet beforehand. From the video call, to dropping him off, Niamh was very communicative and provided updates throughout the day. Highly recommend her if you are in the Chicago area or traveling with your pet and need someone reliable to watch them!”

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Bassey A.
Sitter Profile Image: Kathleen K.
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Kathleen K.
Star Sitter
from
$48
per night
5.0 out of 5 stars
• 11 reviews
6 repeat clients
3 years of experience
Evergreen Park, IL, 60805

“Nemo took to Kathleen right away. She kept him busy with walking and playing with her children. She is a dog lover! He is as in good hands. Sent several pics too. Would definitely ask her to sit again.”

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Linda B.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
• 278 reviews
99 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

“Tamara was great, just like last time. She provided updates, pics and I really feel calm that my Nina is being cared and loved. Highly recommend.”

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Daniella V.
Sitter Profile Image: Thomas Q.
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Thomas Q.
from
$30
per night
5.0 out of 5 stars
• 4 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: Manuel P.
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Manuel P.
from
$42
per night
4.9 out of 5 stars
• 62 reviews
21 repeat clients
8 years of experience
West Lawn, Chicago, IL, 60629

“Sent updates with pictures of my dog that I appreciate-Manuel is kind and respectful, excellent communication -would recommend pet sitting or boarding again”

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Angela C.
Sitter Profile Image: Kyla R.
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Kyla R.
Star Sitter
from
$42
per night
4.9 out of 5 stars
• 89 reviews
35 repeat clients
15 years of experience
East Garfield Park, chicago, IL, 60624

“I’ve booked with Kyla three times now and she’s been phenomenal! She’s very communicative and always sends pictures and updates on how Koda is doing and getting along with the other pups. She’s also very attentive to his behaviors (eating patterns, socializing etc). Koda is happy to be dropped off and also if happy and tired out when I pick him up. I would highly recommend booking with Kyla!”

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

“Katie and Java did a good job sending photos and updates. Katie is pleasant to work with and was flexible in allowing me to pick up my dog a day early. Thank you Katie !”

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Andrea S.
Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$58
per night
5.0 out of 5 stars
• 79 reviews
25 repeat clients
30 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: Christina L.
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Christina L.
from
$55
per night
5.0 out of 5 stars
• 65 reviews
21 repeat clients
15 years of experience
West Town, Chicago, IL, 60622

“Per usual, Cocoa was in the best hands with Christina. She loves going over, so much so she dragged me there this time. I love all the updates and never have any second thoughts dropping her off with Christina!”

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Marlene S.
Sitter Profile Image: Lech S.
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Lech S.
Star Sitter
from
$49
per night
4.9 out of 5 stars
• 108 reviews
44 repeat clients
10 years of experience
West Town, Chicago, IL, 60647

“Mack seemed to have a great time playing with Rizzo, and we really appreciated the pic and video updates of how things were going while we were gone!”

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Randy & Amy O.
Sitter Profile Image: Samantha M.
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Samantha M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 31 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: Jennifer N.
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Jennifer N.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 286 reviews
129 repeat clients
6 years of experience
Lower West Side, Chicago, IL, 60608

“Jennifer is excellent!! Total lifesaver taking my dog at the last minute for several days while I was out of town. I loved the videos and pics!! So nice to know our dog was having as much fun as we were 😊😊😊”

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Rachel B.
Sitter Profile Image: Angel V.
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Angel V.
Star Sitter
from
$47
per night
5.0 out of 5 stars
• 131 reviews
35 repeat clients
15 years of experience
Humboldt Park, Chicago, IL, 60624

“Angel took great care of Bean while we were gone for our extended vacation. He was very flexible on dates/times and communicative about how my dog Bean was doing while away.”

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Talia O.
Sitter Profile Image: Magdalena M.
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Magdalena M.
Star Sitter
from
$38
per night
5.0 out of 5 stars
• 19 reviews
6 repeat clients
3 years of experience
Lower West Side, Chicago, IL, 60608

“Magdalena took incredible care of Remi and Spud while we were away. She was punctual, communicative, and sent great photo updates each visit. Remi and Spud were calm, well-fed, and happy when we got back. We’ll definitely be rebooking with Magdalena in the future and highly recommend her to anyone looking for a trustworthy cat sitter!”

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Nate P.
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1Global data from Rover (November 2025)