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. Damien

Home full-time with a fenced yard

Chicago Lawn, Chicago, IL, 60629

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

"Damien has an absolute love for all animals, especially dogs! He shows such a passion for every breed and size of dog. As a matter of fact, he loves to call... (more)"

2. Deepti

A fun & active home away from home

Near West Side, Chicago, IL, 60607

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

"Deepti is very nice and always willing to help me out in a pinch. She is amazing with my golden retriever, Stanley. He can be a bit fearful and needs lots of... (more)"

3. Jackie

Calm and friendly dog lover

Loop, Chicago , IL, 60601

Drop-In Visits, Dog Walking

"Jackie has been a life-long animal lover, helping to raise two Calico cats and three Labrador retrievers She has often expressed what a joy it is to come ho... (more)"

4. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

17 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)"

5. 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)"

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)"

7. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 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)"

8. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

5 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)"

9. Christian

PAWS volunteer,rescuer

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)"

10. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 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)"

11. Nikki

I am an animal lover to the end.

Woodlawn, Chicago , IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

About: I'm an owner of a playful energetic nine year old boxer. Whenever you see me, you're sure to see my dog Marley. I'm very active so dogs usually ti... (more)

12. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

5 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. 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)"

14. 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)

15. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"Courtney was great- she was able to come watch my cat over the holiday with short notice! She is extremely friendly and responsible. She sent me updates and ... (more)"

16. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"LeAnna was great with my dogs and kept me updated throughout the day. Thank you!! (more)"

17. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Hello, Rover! Simone has cared for my pup, Honey on several occasions & I have never come home to an unhappy pet! She is kind and where Honey is concerned... (more)"

18. Hayley

Flexible, reliable, and available!

Bridgeport, Chicago , IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Hayley cared for our dogs many times over the course of several years. She was frequently willing to do overnight stays when we needed. Hayley is fantastic ... (more)"

19. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Rebba is incredibly compassionate and loving with dogs. She genuinely cares for them and showed great kindness and care for my late dog. Your dog will be i... (more)"

20. Jenna

Caring Fur Mommy

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Jenna is a fantastic dogsitter who took excellent care of my akita, Sabriel, while I was at a work orientation for several days. Sabriel adores her, and Jenn... (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: