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. Madalyn

Graduate Student Who Loves Dogs

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Maddie had been a dog sitter for our dog Benny for the past 5 years. Benny is 14 years old and unable stay at kennels due to his anxiety. Maddie is patient w... (more)"

2. Karolina

Karo the Dog Whisperer™

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)"

3. Corbin

A happy dog, makes a happy world!

West Town, Chicago, IL, 60642

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

1 repeat client

"Corbin is a trustworthy and caring human that your pup will love! I'm so lucky to have him in my and my pup's life. He is my go-to whenever I need anyone to ... (more)"

4. Laura

Capable, Caring Dog Lover

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

4 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)"

5. Sara

Always home to tend to your doggy!

Lower West Side, Chicago IL, IL, 60608

Dog Boarding, Drop-In Visits, Dog Walking

"Sara is one of the most responsibly caretakers for dogs that I know, and her genuine love of dogs specifically makes her an excellent candidate as a dog sitt... (more)"

Confirmed Memorial day Availability
6. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

43 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)"

Confirmed Memorial day Availability
7. May

Always home cuddling :)

Near North Side, CHICAGO, IL, 60611

Dog Boarding, Drop-In Visits, Doggy Day Care

"May and Summer were great hosts. Benny enjoyed his time in Chicago. Summer is a very sweet and cute Shiba Inu and gets along with Benny so well. May is very ... (more)"

8. 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)"

Confirmed Memorial day Availability
9. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

21 repeat clients

"重磅推荐!Enoch真的是一个负责任又爱动物的cat sitter!I strongly recommend Enoch to everyone as a cat sitter. He loves animals. And he takes care of my cats very well. I am loo... (more)"

Confirmed Memorial day Availability
10. Ashley

You'll get ALL the puppy pics! :)

West Town, Chicago, IL, 60642

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

3 repeat clients

"Ashley went above and beyond while watching my cat while I was out of town. She sent me several pictures and updates on everything he was doing. I will defin... (more)"

11. 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)"

12. Irena

Dog-lover and calming, gentle force

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Irena has a terrific love of dogs and a great compassion for animals! I have and would recommend her to anyone looking for a kind, dedicated person to work w... (more)"

Confirmed Memorial day Availability
13. Jennifer

I brush my dogs teeth everyday!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Jennifer made me feel comfortable booking on Rover for the first time. We love her!! (more)"

Confirmed Memorial day Availability
14. Morgan

Puppy and dog loving PT student

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"If you're looking for a great dog sitter, look no further! Morgan is wonderful with dogs and will love your dog like her own. She has experience taking care ... (more)"

15. Christine

Evening & Weekend Dog Walker! :)

Near West Side, Chicago, IL, 60607

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

7 repeat clients

"Christine is a very responsible and loving dog walker with tons of energy and enthusiasm. Our dog loves when she comes by and has so much fun during their wa... (more)"

16. Flor

It will be an adventure with snacks

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I had the best experience with Flor, she took great care of my very feisty dog, haha, Lucy. They spent quite a few hours together and she constantly kept me ... (more)"

Confirmed Memorial day Availability
17. Sasha

Dogs are my best friends!

Near West Side, Chicago, IL, 60607

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

4 repeat clients

About: I can’t wait to meet your best friend. In college I was on a research team where we trained blind and deaf dogs to prove they are just as socialabl... (more)

Confirmed Memorial day Availability
18. Mariah

A walk a day keeps the vet away!

Lower West Side, Chicago, IL, 60608

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

1 repeat client

"Mariah Morris is an incredibly caring and reliable dog sitter. She loves dogs and gives much attention and time to them. Guaranteed you will receive the best... (more)"

Available this weekend
19. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Collin is always so wonderful with Scrappy and gives him tons of attention and affection. He always looks so happy in his pictures on the Rover Card. (more)"

20. Maria

I’ll play heavily with your pup

Near South Side, Chicago, IL, 60616

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

"As Maria's roommate, I see her as a very serious and passionate individual as a dog caregiver. She's a great dog companion, extremely loving, not to mention ... (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.