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. Laura

Capable, Caring Dog Lover

West Town, Chicago, IL, 60622

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

2 repeat clients

"Laura is friendly, kind and very experienced with dogs. She is so thoughtful around making each individual dog feel comfortable and happy. We met her a few w... (more)"

2. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"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)"

3. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

34 repeat clients

"One of my cats is extremely shy, and Megan was able to befriend him easily! I was amazed to see pictures of him being friendly and social after just a coupl... (more)"

4. Madalyn

Graduate Student Who Loves Dogs

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Maddie has cat sat for me several times in the past and has always been super helpful/flexible. She gave me updates, sent pics, and followed my cats normal r... (more)"

5. Caraline

Experienced & Certified Pet Sitter

Loop, Chicago, IL, 60606

Drop-In Visits, Dog Walking

5 repeat clients

"Caraline is the ultimate professional and takes such good care of your pet. Kofi loves her to pieces. She is trained in many different pet care skills and is... (more)"

6. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

22 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)"

7. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

2 repeat clients

"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)"

Available this weekend
8. Natalie

Dog lover in the south loop

Loop, Chicago, IL, 60605

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

"Natalie is my go to person when I need some to watch Nova! Nova has the best time getting cuddles and playing with her dog Roscoe. Nova is so excited every ... (more)"

9. Zac P. and Mugi

We make those tails wag!

Loop, Chicago, IL, 60605

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

2 repeat clients

"Zac has watched our dogs and cat on and off for several years and he has done a great job! He is reliable, on time and flexible to meet our needs as a family... (more)"

10. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60601

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I cannot think of anyone to recommend more heartily than Ivana to care for dogs. Not only is she one of the biggest dog-lovers I know, she is one of the bes... (more)"

11. Lorin

Let me love your dog, like my own!

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

3 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)"

12. Stacey

I Love Animals and Animals Love Me

Douglas, Chicago, IL, 60616

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

1 repeat client

"Every pet I've ever had Stacey took care of for me. I would honestly get jealous because my pets loved her more then me. She would tell what they wanted. She... (more)"

Available this weekend
13. Kj

Let's take a walk in the South Loop

Near South Side, Chicago, IL, 60616

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

"Our dog Grizz is somewhat intimating - he’s big, black and has a ferocious bark - yet Katie was able to connect with him. He loves and listens to her. He als... (more)"

14. Jean

Very friendly and active dog lover!

Lower West Side, Chicago, IL, 60608

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

"Jean is the best! She is great with dogs and mine absolutely love her. She is responsible, kind and the most loving caregiver. I'd recommend her to anyone! (more)"

15. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Tina was wonderful with Brady! She is responsible and sweet and sent me the cutest pics of Brady! This was my first time using Rover and I'm so happy to have... (more)"

16. Stetson

Your dog is in good hands!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Stetson is such a responsible and caring young man. He took care of our dog and cats while we were gone and we were able to enjoy our trip knowing he was the... (more)"

17. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Crystal is the ideal cat sitter, she loves animals and I had no doubt my cat was in caring hands while I was out of town. (more)"

18. Emily

~ Prices Vary, Name your Price ~

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emily watched my dogs many times while I was away on business trips and I always feel bad leaving them but she always cheers them up. She also has really aff... (more)"

19. Daric

I love all shapes and sizes of dogs

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Daric is an extremely loving and highly experienced animal caretaker. He has had dogs as pets his whole life and is the go-to person whenever anyone has an a... (more)"

20. 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)"


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.