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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability: 4th of July
Autumn F.
1.
Gentle, Engaging, and Hard to FazeNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Autumn was awesome! I always give a boatload of directions for my dogs, and she was really great about it all. Plus, the first time I booked her, she really had… (more)

from
$25
per visit
Calendar Recently Updated
Justin L.
2.
Active dog lover with free timeWest Town, Chicago, IL, 60642
Drop-In Visits, Dog Walking

Justin was so friendly and communicative! He checked in on my cat and even stayed to play. Highly recommend. (more)

from
$17
per visit
Calendar Recently Updated
Monica & Calvin M.
Your fur baby's new best friends!Lower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Monica and Calvin are absolutely amazing. They both looked after my two shy and skittish cats with so care! I really appreciated all the detailed updates and pi… (more)

from
$20
per visit
Confirmed availability: 4th of July
Peyton V.
4.
I will love pet like my own :)Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Peyton helped with our two cats for over 2 weeks. She was very flexible with our strange request for a mix of daily check-ins and overnights. We have one cat … (more)

from
$42
per visit
Confirmed availability: 4th of July
Katie L.
5.
Hey pet parents! My name is Kate!Lower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Katie was wonderful!! She was very responsive and eager to get all of my information leading up to when I was going away. She sent photos and updates daily, and… (more)

from
$25
per visit
Confirmed availability: 4th of July
6.
Fun walksNear West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Pablo is awesome! He normally walks our dog but didn’t hesitate when we asked him to watch our cats for the week! Professional and great at sending pics and com… (more)

from
$17
per visit
Calendar Recently Updated
7.
Nurse loves dogsNear South Side, Chicago, IL, 60616
Drop-In Visits, Doggy Day Care, Dog Walking

I would highly recommend Edyta as a member of the Rover team. Edyta and I used to work together as nurses and I can speak to her caring manor. Edyta is also v… (more)

from
$16
per visit
Calendar Recently Updated
Furry Friend’s Welcome!Loop, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Roz was amazing with my Milo (yorkiepoo!!)! I highly recommend her and will continue to use her in the future! BEST DOG CAREGIVER! -thank you (more)

from
$17
per visit
Calendar Recently Updated
9.
Your purfect pet sitterNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Shelby watched our two elderly cats, I was so nervous about leaving them but she immediately put me at ease. She kept me in the loop on a constant basis and als… (more)

from
$15
per visit
Calendar Recently Updated
10.
Pet lover with park nearby!Lower West Side, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Andrea took care of my 6 year old bull mastiff for a weekend and he had a great time. She sent pictures of him playing in the park and seemed to really care abo… (more)

from
$25
per visit
Calendar Recently Updated
11.
Trustworthy & energetic caretakerLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I just graduated college with my masters in accounting and recently moved to Chicago! I have the summer off to study for my CPA exam and am looking f… (more)

from
$15
per visit
Calendar Recently Updated
12.
Welcome from Bailey &ILower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care

Ariel is the true definition of a dog mom. She is very attentive and empathetic for all pets, especially her dog Bailey. She provides a safe and fun environment… (more)

from
$17
per visit
Calendar Recently Updated
13.
Trustworthy and always punctualNear South Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Lais is a great person. She is very responsible, communicative, flexible and easy to work. Your dog will love to spend a time with her. (more)

from
$17
per visit
Calendar Recently Updated
14.
Loving and playful with extra timeNear South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Excellent. Jorie always send pictures and feedback. She is thorough and the cats like her. Appreciate that we can trust that the cats are in good hands. (more)

from
$25
per visit
Confirmed availability: 4th of July
15.
Dog walker. Cat lover. Chicago vetLower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Alex is a great walker and caretaker for our two dogs. He is reliable, flexible with our hectic schedule, and most importantly our dogs just love to see him! On… (more)

from
$20
per visit
Calendar Recently Updated
16.
Extra caring pet lover!Lower West Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Nautica was FANTASTIC!! We booked her to come check in on and feed our 2 cats while we were in California. She was so professional and so communicative. She gav… (more)

from
$20
per visit
Calendar Recently Updated
17.
Zoe 
Verified Enhanced Background Check
Hello. My name is Zoe Kinser.Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Zoe took great care of my cat while I was out of town. She was always so fast to respond, and very punctual. She sent lots of pictures from her visit and let me… (more)

from
$16
per visit
Confirmed availability: 4th of July
18.
Your 1st kitty/doggy visit FREE ✔Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

This was my first time using Rover for my 8 week puppy and it went great. Annie kept in contact the entire time so I knew Penny was in good hands. It definitely… (more)

from
$25
per visit
Calendar Recently Updated
19.
Experience with multiple sized dogsBridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Emliy was Awesome! She did such a great job taking care of our 3 cats! We got updates with pictures everyday while we were gone. She took the time to learn e… (more)

from
$15
per visit
Your dog is my dog!!Near West Side, Chicago, IL, 60607
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jonathan was an excellent dog sitter. My dog Carmelo has so much energy and loves to play. Good thing Jonathan has just as much energy. Carmelo is a hound so hi… (more)

from
$30
per visit

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.