House Sitting in Chicago

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Lauren

Sitter with experience, fully avail

Near North Side, Chicago, IL, 60654

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I currently don't own any dogs, but live in a fully dog accepted home in river north downtown, I'm currently on winter break until february and am ... (more)

2. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"She's a lovely girl. It's hard to give a review, since we weren't home and left shortly after she got to our home, but we liked her very much and would defi... (more)"

Confirmed New Years Availability
3. Daniela

Reliable & Experienced Sitter

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Daniela is the best!! I have a 60 lbs Plott Hound and left to go out of the country for three weeks during which time Daniela stayed at my house. I came home... (more)"

4. Payal

West Town Pet Sitter

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

"I would recommend Payal to anyone that is looking for a compassionate, responsible, animal lover! Through the many times that she has helped walk or watch my... (more)"

Available this weekend
5. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

Confirmed New Years Availability
6. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Cherise is a great dog/house sitter. Our dog Bentley is shy and timid but he took a liking to at their first meeting. Cherise was also very flexible to accom... (more)"

7. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hailey took care of our dog and bird in our home over a long Thanksgiving weekend. She was great! Our pets were well-cared-for, she sent frequent pictures an... (more)"

8. Tatiana

Graduate student who loves dogs!

Near South Side, Chicago, IL, 60605

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Tatiana, did a wonderful job with Bowie. I was out of town for the night and she was able to take Bowie out, feed him, and played with him, so he wouldn't ge... (more)"

9. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Silvia, was awesome! Communication was easy and effective. Plus her experience working at PAWs really made me feel comfortable leaving my 90 lbs, energetic, ... (more)"

10. Shana

Loving. Active. Responsible.

Loop, Chicago, IL, 60605

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Shana was the most amazing sitter we've ever had! She was fantastic with our Corgi, Dom, and we know he had the best time with her as she sent pictures showi... (more)"

11. Jordin

Caring, Warm-hearted and Active

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Jordin took amazing care of my furbaby, Ellie, while we went out of town for a long weekend. Jordin's job was not easy given that Ellie is a high energy, 9-m... (more)"

12. Cristina

Ideal human:Active,fun, friendly.

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Christina was great! We used her recently when we went away for the first time without our pup. She checked in daily to let's us know how Lola was doing and ... (more)"

Confirmed Holiday Availability
13. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"We LOVE Brittany! She took care of Miko with a lot of love and care while were out on a 14 day trip. She stayed in our house, took care of Miko and our home.... (more)"

14. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Catherine has been an animal lover since I've known her. She volunteered at a dog rescue shelter while away at college and continues to volunteer with a Chic... (more)"

15. Eliana

Dream big and love dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Eliana took good care of our dog and cat while she stayed in our home for an extended week trip. She provided timely updates when I inquired about them throu... (more)"

16. Erin

Run And Play All Day!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Erin is an excellent sitter! She's very clearly an animal lover, and I feel completely at peace when I leave Rumi with her. (more)"

17. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Christina took excellent care of my pup while I was away for a long weekend. She communicated regularly and handled small requests, no problem! Will definite... (more)"

18. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Emily was great. She picked our dog up early to help us with our travel arrangements, she sent lots of photo updates and checked in frequently. I felt like m... (more)"

19. Rory

I love and appreciate all pups

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was fantastic and was my first sitter via Rover. She took a last minute job with me (same day for a 3 day long overnight) and was great! I was comfortab... (more)"

Available this weekend
20. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Krystina and Bacon (our furry kid) instantly bonded! This was our first time using Rover and Krystina was very helpful and met with us right away to ease any... (more)"

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Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover - it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy house sitters for your pets--and avoid the kennel.