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.

1. Michelle

Dogs are my light of this world.

Near South Side, Chicago, IL, 60605

Drop-In Visits, Doggy Day Care, Dog Walking

"Layla Michelle cared for my dogs multiple times back in our hometown in Texas. She cared for my 3 year old poodle and my boxer, who back then was a puppy! Sh... (more)"

2. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Our dog Babs had emergency surgery over the Christmas holiday, and we needed someone last minute to look after her while at work and give her some medicine d... (more)"

3. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Five out of Five Stars for Penelope! Our two kids/Italian Greyhounds have very different personalities. Penelope was patient and kind with our shy little gen... (more)"

4. Abby

Experienced Sitter Loves All Pets!

Douglas, Chicago, IL, 60616

Drop-In Visits, Dog Walking

11 repeat clients

"Absolutely excellent! She was available same-day within the hour -- she is awesome. Highly recommended! (more)"

Confirmed Easter Weekend Availability
5. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I can attest to Sidney's abilities as a responsible and loving dog caregiver. Sidney has cared for my elderly dog, who had many health problems at the time. ... (more)"

6. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Breana was a great cat sitter. She sent daily rover cards and made sure my cats had fresh food and water. She also played with them a bit. Definitely will bo... (more)"

Confirmed Easter Weekend Availability
7. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin S. has loved dogs since he was a young boy. I have observed the close bond he has with his dog Joey, for over a decade. Collin also enjoys the neigh... (more)"

8. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 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)"

Confirmed Easter Weekend Availability
9. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

10. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

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

8 repeat clients

"Danielle is a lover of all animals. She is always taking pictures of dogs and cats, and is a great cat mommy. She really is so in love with her Zeus, it is a... (more)"

11. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

Dog Boarding, 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)"

12. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emma was incredibly accommodating; offered to come over for a meet and greet so I could show her around, and we could chat through the stay. She worked with ... (more)"

13. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

14. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jac looked after my sweet corgi, Oliver, while I went away for a weekend. She took amazing care of him! She even sent little pictures of them having fun toge... (more)"

Confirmed Easter Weekend Availability
15. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney was great with my cat, Cathy and she was available within short notice! She sent me photos every day and a video. Even though I've been working with... (more)"

16. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

" Emily has been in the dog-caretaking business for four years. There is nobody I'd recommend before her. Not only is she extremely trustworthy on all levels... (more)"

17. Christian

PAWS volunteer,rescuer, vet student

McKinley Park, Chicago, IL, 60609

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

18. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

4 repeat clients

"Brittany is great! Thanks for taking care of our pup ? (more)"

Confirmed Easter Weekend Availability
19. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I have 14 years experience with a variety of animals, including exotics. I have taken care of animals with special needs and medications. While i... (more)

20. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"My chocolate lab is like my baby, that being said I'm extremely picky with who I will allow to watch him. What I appreciate most about Paige is not just h... (more)"

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Learn About Premier

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: