Pet Setting & Drop Ins in Grand Boulevard, Chicago

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

Confirmed President's Day Availability
1. 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)"

2. 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)"

Confirmed President's Day Availability
3. Paul

I will run with you dog

Loop, Chicago, IL, 60601

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

18 repeat clients

"Paul is awesome. His updates were amazing and assured me that my dog was being taken care of. Will definitely refer him and continuing to use his services. ???? (more)"

4. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

17 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 President's Day Availability
5. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Britney loves all kinds of dogs. She enjoys their company as much as they enjoy hers. She would be a great asset to your company. (more)"

6. Jessica

Home full time-

Near South Side, Chicago, IL, 60616

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

"Jessica is amazing!! She is exactly what you dream a pet sitter could be - enthusiastic and genuinely loving towards your pets, while also being mature and r... (more)"

7. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

22 repeat clients

"This is the second time Payal cat sits for us! she is lovely with the kitties, communicative and very thoughtful. She checked in on them twice somedays and e... (more)"

8. Brenna

I'm PAW-sitive I'm the best match!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Brenna is very reliable and caring toward dogs. She has cared for her own pets, worked at a doggie daycare center, as well as babysat humans. Brenna is... (more)"

9. Christian

PAWS volunteer,rescuer

McKinley Park, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Christian was awesome and extremely accommodating with such short notice! He came to a meet and greet literally the night before we needed him. He was friend... (more)"

10. Vivian

Experienced walker + home full-time

Lower West Side, Chicago, IL, 60608

Drop-In Visits

About: Hi I'm Viv! I work from home as a freelance photographer in the Pilsen area. My schedule is very flexible and I can tend to your dog at any hour... (more)

11. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"We went away for a several week vacation, and Tom was amazing with our fearful dog. Our dog has a disability, is fearful of strangers in her home, and can re... (more)"

12. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Dog Walking

13 repeat clients

"Netiya was amazing!!! We had to book a cat sitter last minute and Netiya was both very responsive and flexible! She sent us photos of our cat while we were a... (more)"

13. 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)"

14. Nicole

We'll put a Woof over their head!

Near South Side, Chicago, IL, 60616

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

4 repeat clients

About: Why board your pet in a loud, cramped cage at a kennel when you can take them to a nice, comfy home where they can run free? While here, they'll re... (more)

15. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

16. Haley

Young Professional Works from Home

Bridgeport, CHICAGO, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"My wife works as a reporter for a famous news agency and was on a long term assignment in the middle east when she was captured and imprisoned by some local ... (more)"

17. Eva

Lifetime Dog Lover & Future Vet!

Kenwood, Chicago, IL, 60515

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I have known Eva for several of years, we are great friends and there is no other person I would recommend to watch my pet besides her. I would allow her to ... (more)"

Confirmed President's Day Availability
18. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

"I have come to know Craig as a good and caring person. I have witnessed him interacting with dogs on several occasions and he has displayed genuine concern f... (more)"

19. Lily

Diligent student with experience

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"If I would trust anyone with my pet, it would be Lily. She is so responsible and on top of things that I know she would give the utmost care to my dog. Also,... (more)"

20. Alejandra

College student w/ a love for pups!

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

2 repeat clients

"Alejandra is one of the most caring and gentle people I've had the pleasure of knowing, and it's a fact that she spreads her loving nature to fellow humans a... (more)"

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 owners have reviewed sitters in Grand Boulevard, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Grand Boulevard pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Grand Boulevard, Chicago who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Grand Boulevard, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including: