Pet Sitting in Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Sitter Profile Image: Shimmy G.
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Sitter Profile Image: Shimmy G.
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1. Shimmy G.

Star Sitter
I love my pups & I’ll love yours!
Near South Side, Chicago, IL, 60605
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
150 reviews
27 repeat clients
from
$20
per visit
Profile image

Shimmy is wonderful with my pup! She gives him lots of great play time and takes great photos. I trust that he is in good hands when Shimmy comes over!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Niko F.
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Sitter Profile Image: Niko F.
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2. Niko F.

Star Sitter
Ensuring your pets safety/happiness
Lower West Side, Chicago, IL, 60616
0.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
40 reviews
27 repeat clients
from
$22
per visit
Profile image

Thank you so much for all the photos and updates! Baker was happy to have us home but with your care he was well looked after. If anyone is looking for a cat sitter I can highly recommend you as the affection and play time you give was well worth every penny. Thank you for taking care of our boy.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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3. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60616
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$21
per visit
Profile image

This is the 4th or 5th time that Crystal has been helping us taking care of Boba and Pudding. They absolutely love her. There was an incident during the stay, but Crystal was very communicative and did her best to help resolve it. We couldn’t ask for a better sitter.

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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4. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
118 reviews
36 repeat clients
from
$20
per visit
Profile image

Emily did a great job with my cats! She was very attentive to their needs and spent a lot of time with them, and all of her communication was prompt and thorough. Highly recommend!

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Sitter Profile Image: Yaneris A.
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Sitter Profile Image: Yaneris A.
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5. Yaneris A.

Happy walks for happy pups!
Chicago, IL, 60608
0.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$20
per visit

Yaneris is the most loving and caring dog owner and sitter I know. She has taken care of my two dogs plenty of times with both visits and walks and house-sitting, and I have to say that my babies love her. She gets them treats, long walks, plays with them at the park, and lets them go in bed with her even when I tell her she doesn't have too. In a nutshell, your pets will be more than take care off in Yaneris's hands.

Sitter Profile Image: Erik W.
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Sitter Profile Image: Erik W.
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6. Erik W.

Star Sitter
Flexible schedule for cats and dogs
Chicago, IL, 60608
0.8 mi. away
Drop-In Visits
5.0 out of 5 stars
15 reviews
3 repeat clients
from
$17
per visit
Profile image

Erik was great! He took care of Ghost like she was one of his own. Tons of photos and updates which is great. Ghost doesn’t like being alone for too long so it was perfect having Erik to check in on her and make sure she gets some love each day.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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7. David K.

Star Sitter
Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
80 reviews
34 repeat clients
from
$25
per visit
Profile image

David was so patient and understanding with my dog, Frankie! He was always on time, willing with work with Frankie’s needs and did an amazing job. I can’t recommend him enough!

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Sitter Profile Image: Samantha L.
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Sitter Profile Image: Samantha L.
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8. Samantha L.

Devoted College Pet Sitter 🐾
Near West Side, Chicago, IL, 60607
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
7 reviews
3 repeat clients
from
$20
per visit

Samantha is one of the most compassionate and nurturing people I know! Her connection and relationship with animals is admirable. From caring for her own five dogs with the utmost passion and dedication, she’s been a loyal choice for me whenever I have dog sitting needs. Amongst our friends, she’s reliable and trustworthy whenever we have a pet sitting task since she’s able to adapt and problem-solve when a situation gets out of hand. I highly recommend her for any and all of your pet needs! She excels at communication and empathizes with all of your worries which she quickly puts to rest.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Amy C.
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Sitter Profile Image: Amy C.
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9. Amy C.

Animal enthusiast with extra ♥️
Chicago, IL, 60605
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
4 repeat clients
from
$20
per visit

Amy was absolutely amazing with caring for our pets and their various needs. Very helpful, kind, and communicative. Couldn’t have asked for better care of our animals! Would highly recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Erin M.
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Sitter Profile Image: Erin M.
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10. Erin M.

Reliable care for your pet
Bridgeport, Chicago, IL, 60608
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
11 repeat clients
from
$19
per visit
Profile image

Erin did a great job with our cats. She hit all of the scheduled visits and sent pictures each time. The boys filed no complaints upon our return. I would rebook in the future.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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11. Ashleigh H.

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
1.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$17
per visit
Profile image

Ashleigh is the perfect sitter. She's responsive and reliable. My dog is shy and she's able to build his trust. I am so happy to have her as my sitter 😊

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Sitter Profile Image: Nicole K.
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Sitter Profile Image: Nicole K.
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12. Nicole K.

Pet Loving College Student
Chicago, IL, 60608
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$15
per visit
Profile image

1st time away from my kids for more than two nights & also this was my 1st time using Rover. Anxiety is running super high but everything went off without a hitch. Nicole was extremely professional an took great care of my kids! I will be using Rover & hoping that I can book Nicole again.

Sitter Profile Image: Sean P.
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Sitter Profile Image: Sean P.
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13. Sean P.

Star Sitter
Feral Cat Caretaker, Friend to Pups
Chicago, IL, 60608
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
48 reviews
11 repeat clients
from
$25
per visit
Profile image

Sean has watched my cat on more than one occasion and has always communicated extremely well and been very professional. My cat is always happy when I get home and I will definitely continue to ask Sean to take care of him. Thanks Sean!

Sitter Profile Image: Kristi T.
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Sitter Profile Image: Kristi T.
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14. Kristi T.

Rover 101
Ready to swap secrets w/ your pets!
Chicago, IL, 60608
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
34 reviews
11 repeat clients
from
$20
per visit
Profile image

Kristi did a fantastic job with my cat, Aria. She doesn’t usually like strangers, but she seemed to like Kristi immediately. Aria seemed well taken care of while I was away and I recommend Kristi for anyone needing a cat sitter.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Julianne F.
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Sitter Profile Image: Julianne F.
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15. Julianne F.

Nurturing Care Giver & Animal Lover
Lower West Side, CHICAGO, IL, 60616
0.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
75 reviews
21 repeat clients
from
$25
per visit
Profile image

Julianne took good care of our cats! We have two scaredy cats and she took the time to find them in their hiding places to make sure they were ok. Her detailed notes and photos gave us peace of mind while we were away. I highly recommend Julianne!

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Sitter Profile Image: Ericka J.
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Sitter Profile Image: Ericka J.
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16. Ericka J.

Loving dog walker 🐶🐾
Bridgeport, Chicago, IL, 60608
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$25
per visit
Profile image

Ericka helped us while we were on vacation by checking on our cat, making sure she had fresh food/water and a clean litter box. She sent us pictures of our kitty and gave us updates at every check-in. Would definitely recommend her!

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Sitter Profile Image: Kelsey S.
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Sitter Profile Image: Kelsey S.
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17. Kelsey S.

I’m an animal lover + tree hugger.
Chicago, IL, 60616
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$20
per visit
Profile image

Kelsey is an excellent pet sitter. My cat is very shy but seemed to take a liking to her immediately. She is a great communicator, very punctual, and thoughtful.

Sitter Profile Image: Jeff O.
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Sitter Profile Image: Jeff O.
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18. Jeff O.

Star Sitter
Caring, reliable pet sitting
Lower West Side, chicago, IL, 60608
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
60 reviews
20 repeat clients
from
$25
per visit
Profile image

Jeff is great sitter. He took care of my kitty when I’m away traveling. He is super nice to our kitty and very responsive as well. Definitely recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sidoni G.
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Sitter Profile Image: Sidoni G.
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19. Sidoni G.

Happy human for happy pups!
Lower West Side, Chicago, IL, 60608
1.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per visit

About: I have over 10 years experience caring for mainly dogs and cats. I’ve cared for pets of all ages and needs, starting with puppies and have had the honor of supporting multiple pets with end of life needs as well. I am a freelance designer that has a flexible schedule and am available starting at 7:30am through early afternoon 1pm. Monday through Friday and open to weekends if needed. I have a car and at home have access to an enclosed patio where pets are free to run around out energy running around and practice daily games and training exercises.

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Sitter Profile Image: Jesica G.
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Sitter Profile Image: Jesica G.
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20. Jesica G.

Loving dog mom
Chicago, IL, 60608
0.9 mi. away
Drop-In Visits, Dog Walking
15 years of experience
from
$18
per visit

About: I’ve had dogs my whole life and make sure to pay extreme attentive care. I follow schedules especially for pups who are potty training! Lots of walks and outdoor time! I currently work part time so I am able to care for pets and looking to do so during my free time. I am available Mondays anytime and weekends after 5pm. I have a fenced yard and one beagle pup at home. Based on the pets needs for walks my pup can come along or be kept separate as needed. I follow a daily walk routine and am able to fit that in to the pets needs. I send updates numerous times throughout the day including pictures and can do check ins when needed!

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Chicago Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Chicago are rated on average 5 out of 5 stars based on 7,553 reviews.

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Rover.com is the simple, savvy way to find and book Chicago house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Chicago on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes the Rover Guarantee, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 300,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Chicago, IL house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

Drop-In Visits