House Sitting in Loop, 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. Tara

New city, new fuzzy friends.

Lake View, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"If you're looking for a caring and responsible individual to watch over your pets when you are away couldn't recommend anyone more. Always received pictures... (more)"

Confirmed New Years Availability
2. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

3. 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)"

4. Nina

Your Dog Will Feel At Home

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Nina was great! We had to go out of town last minute and Nina agreed to watch Ellie 2 days before we needed to leave. She scheduled a meet and greet the next... (more)"

5. Amanda

Experienced Dog Lover and Owner

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Amanda took great care of Benji! I'd highly recommend her -- she gave great updates and was extremely responsive. Most importantly, Benji is healthy and ha... (more)"

Confirmed New Years Availability
6. Rob

A Dog's Favorite Vacation Spot

Near West Side, Chicago, IL, 60606

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Rob is superb with my dog as I am sure he is with every dog he cares for. He seems to understand my dog's needs and wants. But at the same time, Rob doesn'... (more)"

Available this weekend
7. 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)"

8. Timothy

Enthusiastic Dog Lover!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"I trusted Tim with my three dogs and they loved him! I was impressed by how patient and caring he was with each pup. Tim is very dependable and is an experie... (more)"

9. Candice

Sit AND Stay! I do it all :)

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Candice was awesome! It was my first time using Rover and I don't leave my dog with other people very often so I was a little skeptical. She came over for a ... (more)"

Confirmed Holiday Availability
10. Ashland

Not stingy with the belly rubs!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Ashland is amazing with animals. He has always taken care of my "babies" when I go out of town. They get lots of love and attention! I would highly recommen... (more)"

11. Amber

Dog-less dog lover

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"Amber was great! Dogs seemed very happy and calm when we got home and we got plenty of updates while we were away. Will definitely use Amber again! (more)"

12. 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)"

13. Summer

DePaul Student Loves Your Pet

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Summer was very helpful during her weekend stay with Sadie (our 6 month old puppy) and our two cats. I'm grateful for her text updates and her willingness to... (more)"

14. 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)"

15. 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)"

16. Derry

PreK Teacher with a love for dogs!

Lincoln Park, Chicago, IL, 60614

House Sitting, Dog Walking

2 repeat clients

"Derry did a fantastic job with Uma. Uma has a tendency to be weary of new people, especially males but Derry was very patient with her and earned her trust ... (more)"

17. 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)"

18. Bernadine

Professional & Caring Dog Sitter

Near North Side, Chicago , IL, 60611

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Been did a great job with our dog, Franklin. He was very happy and she was very attentive to his special needs. (more)"

Confirmed Holiday Availability
19. Jordin

Caring, Warm-hearted and Active

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Jordin is always great - makes traveling easy. She is on time, provides pictures and updates, and is quick to respond. I absolutely recommend her. (more)"

20. Eliana

I am friendly, punctual, and ready!

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)"

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Learn About Premier

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.