House Sitting In Near South Side 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. 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
2. 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)"

3. 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
4. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

5. 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)"

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 was great! I trusted leaving Tula with her for a few days over the holiday weekend. She gave me updates, sent me a pic, and my house looked untouched... (more)"

8. 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)"

9. 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)"

10. 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)"

11. 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)"

12. Kara

Pet lover with all day availability

Near South Side, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

About: I have experience taking care of all types of pets! I personally grew up with dogs ranging in size from a shih tzu to a saint bernard and now curre... (more)

13. 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)"

14. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Christina was an incredible sitter!! Prior to her staying with my wheaten terrier (Vivian) it was easy to set up a meet/greet with her, and she was very res... (more)"

Confirmed Holiday Availability
15. Jordin

Caring, Warm-hearted and Active

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Jordin did an excellent job with Wrigley. She kept us updated the entire time we were gone and we felt very comfortable leaving. She took great care of him a... (more)"

Confirmed Holiday Availability
16. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

"Brittany was so so great! She was extremely flexible, quick to respond, and kept me updated throughout Royal's stay with her. It was clear Brittany was very ... (more)"

Available this weekend
17. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

18. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is an angel! She loves my sweet baby Ray like one of her own. Sarah has watched Ray on multiple occasions. During their time together she often takes h... (more)"

19. 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)"

20. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Thank you Emily for taking care of Cali while we were gone! Emily was flexible with the hours we needed and gave us an update or two each day. We came home t... (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.