Drop-In Visits in Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Tina is *excellent.* She was wonderful with my 2 large dogs during my first weekend away from home. Her care is extremely reliable, conscientious, and kind.... (more)"

2. Maria

I'm a professional dog whisperer :)

South Lawndale, Chicago, IL, 60623

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Maria is a phenomenal dog sitter. She specializes in presumably big dogs, always keeping her composure no matter what the situation. Dogs always feel a certa... (more)"

3. Patrick

Experienced sitter w/ huge yard

West Town, Chicago, IL, 60642

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

4 repeat clients

"I cannot think of a better dog caregiver than Patrick. Not only has he been an avid dog lover his entire life, he is also incredibly responsible, punctual an... (more)"

4. Hannah

Fun and loving pup lover!

West Town, Chicago, IL, 60622

Dog Boarding, Drop-In Visits, Dog Walking

6 repeat clients

"Hannah was a wonderful help while I was out of town. Very responsive and handled an unexpected issue (possum got in through the pet door) with grace! She was... (more)"

5. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Karolina stays in touch and shows that she truly cares for your pets - it helps so much when you are away! I get notes and photos constantly. I would highly ... (more)"

6. Brittany

Volunteer, Active & Professional

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Brittany was great! We needed someone to check in with our three cats to feed them and take care of the litter boxes. Our often aloof cats were well taken ca... (more)"

7. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

27 repeat clients

"Megan did a great job with my cat Helice when I was out of town for one week. She checked in every day by texting me and sending me photos. When I came back ... (more)"

Confirmed Holiday Availability
8. Natalie

Loop Living and Pup Loving!

Loop, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Natalie is a lifesaver and apparently somewhat of a dog whisperer! She was early and responsible and we are lucky to have found her! (more)"

9. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

1 repeat client

"Britney did an excellent job with Thor. He takes a lot of patience and she had it to give. She was also very good at sending us updates regularly. I highly r... (more)"

10. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

14 repeat clients

"Enoch was very friendly and personable with both me AND my cats! He was excellent with prompt communication about how much (or little) the cats were eating, ... (more)"

11. Alexandria

Pup Adventures with Alex

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Alex was great! She took my reservation at the last minute for Thanksgiving weekend to take care of my cat Bean. She stopped by daily to feed Bean and play w... (more)"

12. Jacob

Love to Walk!

Near West Side, Chicago, IL, 60607

Drop-In Visits

2 repeat clients

"Jacob recently cared for my two dogs when I was out of town on a work trip (drop in visits) and I would highly recommend him. In addition to being calm and ... (more)"

13. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

2 repeat clients

"Adriana did a great job when watching my two dogs last week when I was out of town for work. She was reliable, followed all directions, and was very good wi... (more)"

14. Chelsea

Animal Trainer who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"This is the first time for us using Rover.com and I have to be honest with you, Chelsea has really set the bar high she is amazing with animals. She made su... (more)"

15. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

20 repeat clients

"Payal was a better dog-sitter than I could have hoped for. It was our first time leaving Zeke alone with a stranger and she was very caring and attentiveness... (more)"

16. Sara

UIC area dog lover, reliable & fun

Near West Side, Chicago, IL, 60607

Drop-In Visits, Dog Walking

"Sara is extremely careful and caring and will be the perfect caregiver for your dog! She did a great job watching over my retriever while I was on vacation, ... (more)"

17. Ashley

Flexible schedule; long walks

Near North Side, Chicago, IL, 60654

Drop-In Visits, Dog Walking

1 repeat client

"Ashley was absolutely wonderful! She was very thorough in describing her visits with my dog & I almost felt like I was home with them. I returned home from m... (more)"

Confirmed Holiday Availability
18. Paul

I will run with you dog

Loop, Chicago, IL, 60601

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

15 repeat clients

"Paul was wonderful! He kept us updated on how our kittens were doing with tons of pictures and videos. We definitely plan to use him in the future. Thanks Paul! (more)"

19. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

1 repeat client

"Alex took great care of my cat when I was traveling! She sent pics and kept me updated during my trip. I would recommend Alex to anyone who needs a responsib... (more)"

20. Lorin

Let me love your dog, like my own!

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Lorin was great! Our kitties seemed to love her by the pictures she took. She was consistent with her drop in visits. We came back from vacation to a clean h... (more)"


Rover.com is the simple, savvy way to find and book Rogers Park, 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 Rogers Park 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 premium pet insurance, 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 65,000 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 Rogers Park, Chicago, IL house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.