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.

Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Niko F.
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Sitter Profile Image: Niko F.
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1. 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
34 reviews
24 repeat clients
from
$22
per visit

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.

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Sitter Profile Image: Shimmy G.
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Sitter Profile Image: Shimmy G.
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2. 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
144 reviews
27 repeat clients
from
$20
per visit

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: 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, 60653
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$21
per visit

Crystal was amazing with my reactive border collie! She took her time introducing herself and helped Zuri be super comfortable on a walk when she’s not used to being taking out by others!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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4. Michael D.

Star Sitter
Dog Lover Ready to Love Your Dogs
Lower West Side, Chicago, IL, 60608
1.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
10 repeat clients
from
$25
per visit

Michael was easy to work with and it really seems like he enjoys spending time with animals. Any pet would be in good hands with him. Will definitely be in touch with him again!

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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5. 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

Emily was fantastic! She took lots of time to play with my two cats and provided me with thorough updates on how they were doing each day. She was also very responsive and communicative. I would definitely book her again!

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Sitter Profile Image: Mia M.
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Sitter Profile Image: Mia M.
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6. Mia M.

I love all animals big and small
Chicago, IL, 60607
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$20
per visit

mia is great! good communication throughout the drop-in and was very attentive to my anxious dogs requirements

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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7. 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

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 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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8. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$23
per visit

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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Sitter Profile Image: Samantha L.
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Sitter Profile Image: Samantha L.
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9. 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
6 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: David K.
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Sitter Profile Image: David K.
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10. 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
79 reviews
34 repeat clients
from
$25
per visit

David took great care of our kitty for a weekend of drop-in visits! Super responsive, very detailed updates with photos, and overall great communication.

Sitter Profile Image: Kristi T.
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Sitter Profile Image: Kristi T.
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11. 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

Kristi was our first experience using Rover and I would absolutely book her again. She is flexible, responsive, and always on time. Kristi sends photos after each visit, which were very reassuring! Our cat was well taken care of and seemed at ease in her company.

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Sitter Profile Image: Kathryn K.
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Sitter Profile Image: Kathryn K.
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12. Kathryn K.

Your furry friends favorite walker!
Near West Side, Chicago, IL, 60608
1.1 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$20
per visit

Kathryn has always shown enthusiasm towards taking care of pets around her. As a family friend, I’ve watched her take care of my parent’s small dog in a caring and responsible manner. I know she also enjoys taking care of her friend’s cats whenever she gets the chance! She’s a big animal lover.

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Sitter Profile Image: Nicole K.
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Sitter Profile Image: Nicole K.
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13. 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

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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Erin M.
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Sitter Profile Image: Erin M.
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14. 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

We loved having Erin cat sit for us! She was on time, communicated well and was extremely considerate of other home needs! We would highly recommend her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sidoni G.
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Sitter Profile Image: Sidoni G.
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15. 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.

Sitter Profile Image: Sean P.
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Sitter Profile Image: Sean P.
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16. 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
47 reviews
11 repeat clients
from
$25
per visit

Sean was very thoughtful when it came to my pet. He is kind and very communicative and i can tell cares about my pet's needs. I had a very good experience booking Sean and I would definitely book Sean again.

Sitter Profile Image: Jeff O.
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Sitter Profile Image: Jeff O.
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17. 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
19 repeat clients
from
$25
per visit

Jeff did a wonderful job with my 4 cats. I was really nervous leaving them alone with a stranger, but from the beginning he was very responsive and communicative. When he came by for the meet and greet it was clear he was a cat lover, and took the time to get to know my cats individually. I left him very complicated instructions (4 cats, 4 different diets, all 4 needed medicines), and he handled it like a pro. He sent me a ton of updates, photos and videos, and it was clear he put a lot of time into playing with them, petting them, bonding with them... I felt like I was able to relax and enjoy my vacation because they were in good hands. Highly recommend him!

Sitter Profile Image: Erik W.
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Sitter Profile Image: Erik W.
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18. 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

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.

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Sitter Profile Image: Ericka J.
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Sitter Profile Image: Ericka J.
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19. 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

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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Julianne F.
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Sitter Profile Image: Julianne F.
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20. 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
$23
per visit

Julianne is great and I am impressed with how fast she bonded with one of my cats that never get along with sitters. I received detailed information of the cats wellbeing and home which was awesome considering I was busy with work overseas. The Rover app is the only thing that is challenging.

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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.

Check out the Pet Sitting & Drop Ins in your neighborhood:

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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