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.

Available this weekend
1. Maya

Full time availability

Grand Crossing, Chicago, IL, 60619

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

"Maya is a wry patient and caring person. She's grown up with pets her entire life and has a loving Yorkshire terrier that's she's had since a young teenager... (more)"

2. Yvonne

Greyhound Mom: Loving Sitter/Walker

Lower West Side, Chicago, IL, 60608

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

"Yvonne is a very loving caregiver for dogs and pets in general. She is very responsible and doesnt take any situation for granted. I would highly recommend her. (more)"

3. KC

Loving Pet Sitter/Nursing Student

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"KC was great and sent pictures each day. I really appreciated her amazing communication before, during, and after the pet sitting! (more)"

4. 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)"

5. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 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)"

6. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Our pups love Crystal and I can't imagine a better person to be part of our dog team. So grateful Crystal was able to help. (more)"

7. 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)

8. Madison

Pup Loving Student

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Madison was great! Very communicative and sent me photo updates of my cat each day which I appreciated immensely. I would use her services again! (more)"

9. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

9 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)"

10. 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)"

11. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Netiya watched my cat, Harvey, while I was away on an extended weekend. She updated me with photos and messages! Would definitely use Netiya and her services... (more)"

12. Anne

Grad Student Ready to Love Your Pup

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

2 repeat clients

"Anne took very good care of my cats and sent me updates while I was away. (more)"

13. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Simone did an incredible job watching my dog and cat while I was out of town! I have a very large dog (150 lbs) who is fairly high maintenance (on meds, has ... (more)"

14. 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)"

15. Phoebe

Lots of availability - Lots of love

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Phoebe took excellent care of our Pomeranian while we spent our annual week at Disney World. It seemed like she and Moxie really bonded - we felt like we lef... (more)"

16. Florence

Animals are my friends!

Hyde Park, Chicago, IL, 60637

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

"Flo is the best! I would trust her with my dog any day. She is reliable, conscientious, and great with all kinds of animals! Definitely pick Flo to take car... (more)"

17. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"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)"

18. 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)"

19. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor cares for all living things with unparalleled empathy. She is kind to and patient with animals. My roommate's cats hate me but they love Eleanor. (more)"

20. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

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

"Blaize is an excellent petsitter. She's a kind, reliable, and thoughtful person--and a pet-owner herself. You'll have peace of mind when you're away from to ... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: