House Sitting in Grand Crossing, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

1. 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)"

2. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

3. Megan

Pets are my life! I love them!

Chicago Lawn, Chicago, IL, 60629

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have owned dogs my whole life. I got my first dog as a Christmas present when I was in third grade. Ever since then, I have been taking care of m... (more)

4. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits

2 repeat clients

"Jac was great. She came over to meet our 2 big dogs and they got along swimmingly. She was communicative and easy to reach when I wanted to check in. I would... (more)"

5. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is an angel! She loves my sweet baby Ray like one of her own. Sarah has watched Ray on multiple occasions. During their time together she often takes h... (more)"

6. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

7. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

1 repeat client

"Brittany is a CHAMP. She's a savvy handler and trainer who communicated well, followed instructions perfectly, navigated both our dog's behavioral issues and... (more)"

8. Myk'La

Energetic, artsy, happy and caring

Chatham, Chicago, IL, 60619

House Sitting, Drop-In Visits, Dog Walking

"Myk'La is a awesome person and some one i'd highly recommended for the Dog Caregiver position.She posess a high spirit personality along with an outgoing and... (more)"

9. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

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

7 repeat clients

"Amazing, Hendrix seemed to love his vacay away from me as much as I enjoyed my vacation. Sent me updates and pictures while I was gone and when my flight got... (more)"

10. Jordan

Dog Lover and Rescuer

Calumet Heights, Chicago, IL, 60617

House Sitting, Drop-In Visits, Dog Walking

"Jordan is a kind, dedicated woman who gives her all to her passions. Her love of animals is enormous, as is her ability to care for them. She stands out by ... (more)"

11. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

"Paige is very caring and patient with dogs. She has rescue dogs of her own and one with behavioral problems. She has been very patient in caring in helping t... (more)"

12. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

1 repeat client

"Kimberly is the ultimate dog lover. She cared for her dog Kobe for over 17 years, taking him wherever she went! Kim is responsible, nurturing, and kind which... (more)"

13. Stephen

Walking, Bordering/Sitting Training

Beverly, Chicago, IL, 60643

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

7 repeat clients

"What a great service Stephen provided I don't think my dog even missed me much! A real dog lover who sincerely tried to help my big shelter dog with many issues (more)"

14. Kennedi

Love as if it's your own.

Calumet Heights, Chicago , IL, 60619

House Sitting, Drop-In Visits, Dog Walking

About: I was the fortunate ten year old girl, no siblings who grew up with the responsibility of several children ( dogs, frogs, snakes, cats, etc. lol). ... (more)

15. Yesenia

Dog Trainer/Handler

West Englewood, Chicago, IL, 60636

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

About: My name is Yesi and I've been working with animals (mainly dogs) professionally for 6 years now. I started off as an adoption counselor for an anim... (more)

16. 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

"The best dog sitter we ever had. She was very loving to all 3 of our babies, as if they were her own. Our newest addition, is a 100 pound lap dog (at least h... (more)"

17. Brittanie

Im friendly energetic and patient

Woodlawn, Chicago , IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"I have a poodle and Brittanie was reccomended to me by a friend I have been using her for up to three years now and she has done plenty of drop ins and walks... (more)"

18. Allena

Loving animals is my pleasure.

Englewood, Chicago, IL, 60621

House Sitting, Drop-In Visits, Dog Walking

"Allena is perfect if you want you dog in good hands. She watched my puppy for a week while I was out of town and even video chat me when I wanted to do a che... (more)"

19. Catalina

Catalina, Dog Lover

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Catalina has always had a special relationship with dogs. When she was growing up, at various times, she had labradors, neapolitan mastiffs, rottweilers and ... (more)"

20. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

3 repeat clients

"Thank you so much Marty for being available last minute and taking care of my pup! You are a life saver and Jessie really had a good time with you. He even c... (more)"

Experience exceptional service and a personalized match

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

Learn About Premier

Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover - it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy house sitters for your pets--and avoid the kennel.