Pet Sitting & 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.

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1. Jennifer Verified Background CheckRover 101

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jen is awesome, she’s so real and down to earth. She actually cares about my pets (sent me pictures, was willing to work with me when she couldn’t get ahold ... (more)"

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2. Angelica Verified Background Check

Flexible schedule, love all pets!

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Angelica was fantastic helping us out during a busy week. She took tremendous care of our 11 week old golden retriever puppy, attending to his needs as they ... (more)"

3. Andrea Verified Background CheckRover 101

Fun times waiting to be had!

Washington Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Andy did a fantastic job befriending my demanding rescue kitty who doesn’t automatically understand people are his friends. Yet while I was away, Andy patien... (more)"

4. Alicia Verified Background Check

Understanding pet’s needs

Washington Park, Chicago, IL, 60637

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

"Alicia was great! Our dog is very high energy and is a bit difficult to walk but Alicia handled him great! Would definitely book with her again! (more)"

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5. Cassidy Verified Enhanced Background Check

I'll treat your fur baby as my own.

Douglas, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Cassidy is an excellent and caring pet sitter. She really made my vacation more enjoyable and stress-free knowing that my cat was being taken care of by a de... (more)"

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6. Tenley Verified Background CheckRover 101

Experienced Dog Owner & Care Giver

Douglas, chicago, IL, 60616

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

"Tenley is a wonderful and caring pet owner and caregiver. She has had many pets throughout her life. She recognizes the love and patience it takes to properl... (more)"

7. Crystal Verified Background Check

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"I am so happy I found Crystal. It is my second time hiring her to check in on my bunny when I was out of town and she does an exceptional job and I definitel... (more)"

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8. Cameron Verified Enhanced Background Check

Your Pet’s Favorite Auntie

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Cameron helped us out on really short notice. She was helpful and communicative. I’d definitely (more)"

9. Jamie Verified Background Check

Bridgeport trekkers unite!

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Doggy Day Care, Dog Walking

"Jamie is one of the most conscientious dog owners I've met and she has a magical way of training them. My dog is not the most obedient in the world but over ... (more)"

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10. Minhyo Verified Background Check

Flexible, caring, and active!

Hyde Park, Chicago, IL, 60637

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

"Minhyo would make a great walker/sitter for your pet. She's not only an animal-loving person, but she's responsible, compassionate, and trustworthy. You woul... (more)"

11. Arielle Verified Background Check

Student who needs a dog in her life

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Arielle was friendly, punctual and communicative during her drop in visits with my cat. She provided lots of updates and pictures while I was gone for a long... (more)"

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12. Lilia Verified Background Check

Experienced dog lover!

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Lilia was great!! She took the cutest photos of my cat while I was out of town and took the time to play with her :’) great communication on her end. (more)"

13. Ariadne Verified Background Check

An assiduous, punctual dog-lover!

Hyde Park, Chicago, IL, 60615

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

"My dog Sammie and I absolutely love Ariadne! She is always kind and caring, very energetic, and always reliable. Nothing but positive experiences every time ... (more)"

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14. Annie Verified Enhanced Background CheckRover 101

Your Pet's Loving Companion <3

Armour Square, Chicago, IL, 60616

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

"She’s always nice and warm. Think of stokes(my cat) as hers. Now she is stokes’s one of favorite aunt! Haha (more)"

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15. Iuma Verified Enhanced Background CheckRover 101

Short notice? No problem! I ❤️ pets

Armour Square, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Iuma was great with my dogs. She was attentive and excellent with follow up photos and communication. I will highly recommend Iuma to anybody and will defini... (more)"

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16. Marisa Verified Background Check

Animal lover w/ lots of experience

Hyde Park, Chicago, IL, 60615

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

"I've known Marisa as a dog walker for years and she is great with all sizes and types of dogs. She has also taken care of my dog Pug on multiple occasions. S... (more)"

17. Ryan Verified Enhanced Background Check

Reiki Healer and Dog Lover

Douglas, Chicago, IL, 60653

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

"Ryan is punctual, responsible, and loving. As a housemate, he loves to cook meals for the house and is dedicated to having us all partner to make it a clean ... (more)"

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18. Juani Verified Background Check

Your dog’s favorite nanny.

Woodlawn, Chicago, IL, 60637

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

"Juanita is wonderful with pets! She is sensitive, careful, and loving. She loves to cuddle and play with them as well. I can easily recommend her for pet sit... (more)"

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19. Alexander Verified Background Check

Graduate Student and Animal Lover

Hyde Park, Chicago, IL, 60615

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

"Alex is very responsible when dealing with dogs and cats. He has always liked them and is kind and gentle. He is a very honest person and is trustworthy. He... (more)"

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20. Kathleen Verified Background Check

Some of the best people I know...

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Doggy Day Care

"Kathleen G is, seriously, the biggest pet lover I have ever known. She had a wonderful, beautiful dog who passed away last year at age 15. Kathleen cared and... (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: