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.

Calendar Recently Updated
1. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"She was very timely and sent me pictures of the dog which eased my mind while I was gone! I will definitely rebook Ivana! (more)"

Calendar Recently Updated
2. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

14 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)"

3. Holly

Grad Student Home Full Time

Near North Side, Chicago, IL, 60610

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

8 repeat clients

"Holly took the time to meet Monty and I before his walk and she was great! She sent me updates and a Rover card. I really appreciate her thoughtful care and ... (more)"

Confirmed availability
Memorial day
4. Jacob

Full time dog lover

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Jacob is awesome! I left my dog with a friend, who informed me last minute that they would be home some hours later than expected and wanted to know if I cou... (more)"

Confirmed availability
Memorial day
5. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

47 repeat clients

"Megan was quick to respond and left great notes and photos on the check-in card. My cat was well cared for while I was away for a long weekend. (more)"

Calendar Recently Updated
6. Kelsey

Cat and dog lover!

West Town, Chicago, IL, 60622

Drop-In Visits, Dog Walking

1 repeat client

"My parents are veterinarians, I have one cat who is my WORLD, and there’s no reason to look at any more pet sitter profiles—choose Kelsey! She did a PERFECT... (more)"

Calendar Recently Updated
7. Stephanie

Teacher w/ Flexible Summer Hours

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

"Me and my Frenchie LOVE Stephanie! She is our #1 go-to. She is so sweet, reliable, knowledgeable, and takes the best care of fur babies! She sends constant u... (more)"

Calendar Recently Updated
8. Addie

22, responsible, good communicator

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Addie really pulled through when I needed a last-minute sitter for my cat! She is responsible and kept me updated throughout her her visit. Your pet will be ... (more)"

Calendar Recently Updated
9. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

23 repeat clients

"Payal was great with our kitties! she was attentive and made sure that one of our cats was properly hydrated (he only drinks water from the tap). She took gr... (more)"

Calendar Recently Updated
10. Britney

Cozy Home, Large Backyard & LOVE?

Bridgeport, Chicago, IL, 60608

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

About: I am FOR SURE an Animal Lover. Growing up with a house full of cats and dogs (even had a ferret) my experience goes back far. I love taking care of... (more)

Calendar Recently Updated
11. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Tina did a great job taking care of our two cats while we were out of town for a long weekend! She was very responsive to our requests and was readily availa... (more)"

Calendar Recently Updated
12. Kristin

Long walks and lots of love!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

About: My family was always a huge fan of dogs of all sizes, from German Sheppards to Bull Terriers, and even the stray Bichon Frise! I have been raised a... (more)

Calendar Recently Updated
13. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

3 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)"

Calendar Recently Updated
14. Ashley

Home during Day-Will love your baby

Near West Side, Chicago, IL, 60607

Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"You won't be disappointed if you hire Ashley to walk your dog, very trust worthy and she loves dogs. Highly recommend her for dog walking! (more)"

Confirmed availability
Memorial day
15. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

23 repeat clients

"Enoch is a very professional cat sitter. He knows a lot about how to communicate and play with cats. I feel very comfortable to leave my cats with him. He fe... (more)"

Calendar Recently Updated
16. Brendan

Lifetime experience of spoiling!

Near West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Dog Walking

About: Born and raised Chicagoan, have had a dog everyday of my life (volunteered to get my fix in college). Very sensitive and understanding to needs suc... (more)

Confirmed availability
Memorial day
17. Tara

Care for your dog like my own

Bridgeport, Chicago, IL, 60616

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

"Tara took care of my dog Mindy and cat Gonzo over the weekends I was away for work. She sent updates and pictures which I really loved to keep in touch with ... (more)"

Confirmed availability
Memorial day
18. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

5 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)"

Calendar Recently Updated
19. Megan

Reliable, Respectful, Responsive

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

22 repeat clients

"I think the visit went great, I got great pics and a great report. My baby was healthy, happy and safe. Megan asked a lot of great ?s at meet and greet which... (more)"

Calendar Recently Updated
20. Ekaterina

Home full-time - fenced yard

Bridgeport, CHICAGO, IL, 60608

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

"Ekaterina is amazing with dogs! She is loving and has a great energy that my pups adore. She helped me with occasional walks and extended boarding many times... (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.