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.

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1. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jennifer was great to communicate with! We will be asking her to drop-in in the future. (more)"

Confirmed availability
Christmas and New Year
2. Michelle

I love to run and go on hikes

Loop, Chicago, IL, 60606

House Sitting, Drop-In Visits, Dog Walking

"Michelle is awesome. She communicates a lot and sends pics and updates of the dogs and when I come home later, the pups are super happy. I always feel at eas... (more)"

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3. Presley

lifelong pet owner; home full-time

Near South Side, Chicago, IL, 60605

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

"Presley took amazing care of Latika and kept us updated with videos and pictures, she had a great fit with Latika and we will look for Presley for future pet... (more)"

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4. Sanford

Accepting new dog and cat clients!

Near South Side, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Commmunicative and super helpful. Went above and beyond.Will be using his services again. (more)"

Confirmed availability
Christmas and New Year
5. Esther

South Loop, Full-Time Fun

Near South Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

About: Welcome, Rover friends. Consider leaving your friendly pup with me. I'm active and love the outdoors. Our home is clutter and stress-free. Calm wal... (more)

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6. Jonathan

I watch your pets so you can relax!

Loop, Chicago, IL, 60602

House Sitting, Drop-In Visits, Dog Walking

"We had a last minute crisis when some friends could no longer check in on our two kittens and Jonathan saved the day! We contacted him the night before we ne... (more)"

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7. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Though it was for a short period of time we felt very comfortable leaving her with our puppy. The pictures she sent reassured us that our baby was doing just... (more)"

8. Derek

Fun and Friendly Dog Lover

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"I have two cats - one who loves all people, and one who discriminates against men, but that isn't an issue with Derek. After meeting him just a couple of tim... (more)"

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9. Megan

Petsitter looking for new clients!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Megan was amazing! I had to book a few same-week visits, and we weren't able to squeeze in a meet & greet beforehand. I wrote out detailed instructions, and ... (more)"

10. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Karolina is the best! She house sitted for a long weekend and I'm pretty sure our pup was sad we were back and she had to leave. She walked him a LOT and sen... (more)"

11. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

"Eddie always does a great job with our dogs. He’s sensitive to their unique needs and any questions or concerns we have. (more)"

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12. Chelsea

Available all day all summer!

Lower West Side, Pilsen, IL, 60608

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

"Chelsea is the biggest dog lover I know. Since she doesn’t have a dog or her own, this job will give her the amazing opportunity to walk and take care of all... (more)"

13. Lu

Professional cat sitter in the loop

Loop, Chicago, IL, 60601

Dog Boarding, Drop-In Visits

"Lu is a fabulous pet sitter. My cats have special medical needs and Lu took care of everything without any problems. Impeccable communication, thoughtful res... (more)"

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14. Angelica

Home full-time, flexible schedule.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Angelica is a trustworthy person, as well as an incredible caregiver for dogs and humans alike. She responsible and always willing to help out. She has exper... (more)"

Confirmed availability
Christmas and New Year
15. Jacob

A fun, caring and creative person

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"When I went to Miami Jacob took good care of my miniature pincher called Marley Moe. Jacob never failed to follow Marley's daily scheduled activities which ... (more)"

Confirmed availability
Christmas and New Year
16. Robert

Home full-time, close to big parks!

Near West Side, Chicago, IL, 60607

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

About: I've had experience caring for all sorts of different dogs for most of my life. I grew up with a Miniature Schnauzer and English Springer Spaniel, ... (more)

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17. Chenika

Fun & Passionate Sitter!

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits

"Chenika took care of our two cats this past weekend. At our initial visit she was very friendly and made us feel very comfortable about leaving our cats in h... (more)"

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18. Bri

Student wanting all your dogs love

Loop, Chicago, IL, 60605

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

About: I used to go and walk dogs at a shelter. I also trained my 3 year old golden retriever. Him and I do everything we can together when I’m home in Oh... (more)

19. Katlyn

Consistent & Loving :)

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Excellent sitter for my two cats!! (more)"

20. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel is wonderful with my dog! I have a 70 pound pit mix that likes to pull and, while she looks tiny, she manages to control and hold onto Kobe quite easil... (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 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 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.