Dog Boarding in Woodlawn, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Megan

Super South Loop Sitters

Near South Side, Chicago, IL, 60605

Dog Boarding

1 repeat client

"I would highly recommend Megan. We met before our stay to ensure that our dogs would get along. Megan sent lots of updates during Mini's stay, which was re... (more)"

2. Monique

Conscientious dog lover

Woodlawn, Chicago, IL, 60637

Dog Boarding, Drop-In Visits

About: I am a life long dog owner and lover. Your pup will be cared for, played with and have all of it's needs met while you are away. I am the owner o... (more)

3. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

1 repeat client

"Gail was so great with my dog, Oliver. I have a pretty clingy shih tzu and after trying two sitters for him, I thought we just couldn't leave him alone anymo... (more)"

4. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

5 repeat clients

"Marga took care of both my dogs Max and Nala during last weekend. I am 100% happy with her. She was extremely attentive to the instructions I gave (I am a bi... (more)"

Confirmed Holiday Availability
5. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

1 repeat client

"very professional, gentle with our pet (more)"

Confirmed Holiday Availability
6. Saran

Pampering Pooches with a smile!

Washington Heights, Chicago, IL, 60620

Dog Boarding, Drop-In Visits

"Saran C. is Amazing with our little babies, Tiffany and JoJo! My husband and I have 2 mini Yorkies and they are our world. We have such busy schedules, as of... (more)"

7. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

1 repeat client
No Reviews Yet

About: If you need a home away from home for your furry family member contact me today. My family is loving, kind, experienced with animals, and loves dog... (more)

Confirmed Holiday Availability
8. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

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

2 repeat clients

About: Dogs & I: Over the course of my life I have raised several different dog breeds and currently still take care of my 11 year old peek-a-poo, Isabel... (more)

Confirmed Holiday Availability
9. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

29 repeat clients

"Kristal was exactly what I was looking for when my husband & I took an extended vacation! I loved that she was around her home most of the time and had a la... (more)"

10. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

11. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

"Awesome!! Expert dog handler!! Will use again for sure!! (more)"

12. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

"Mindy was amazing!!! By the looks of the pictures, our dog enjoyed his stay! She sent updates about twice a day which was great! I was glad I left him in the... (more)"

13. Dana

Hyde Park Animal Sitter for Hire!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

2 repeat clients

About: Hello! My name is Dana and I've lived with animals since I was born. I've had 2 dogs, 2 cats, and a rabbit, each needing some type of medication or... (more)

14. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"LeAnna is passionate about animals and loves pups of all shapes and sizes. She routinely stops and asks dog owners if she can pet their dogs, always engagin... (more)"

15. Kathryne

Responsible and caring dog owner!

Grand Boulevard, Chicago , IL, 60653

Dog Boarding, House Sitting

"Great sitter.Her dog and my dog got alone well and dream has never been around another dog overnight or let alone over 30 mins.Her home is fantastic.He had ... (more)"

16. Dawn

Choose Dawn! I'm not JUST a soap..

Grand Boulevard, Chicago, IL, 60653

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

2 repeat clients

About: I believe about half of my heart is filled with my love for dogs, the other have is Johnny Depp and Mac and cheese! I've taken care of about 20 dog... (more)

Confirmed Holiday Availability
17. Brandy

Exp. & Resp. Ph.D. animal lover!

Hyde Park, Chicago, IL, 60637

Dog Boarding

"Brandy welcomed my two boxers into her home with open arms. I received pictures and updates everyday and my dogs had a blast with her! I would highly recomme... (more)"

Confirmed Christmas Availability
18. Robbie

animals may think I'm dr Doolittle

Kenwood, Chicago , IL, 60615

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I have experienced small and large dogs throughout my life and I'm in love with animals. I treat animals as if their my children. I hate to see any... (more)

19. Keeshina

PETS ARE HUMANS IN DIFF.FORMS ÔŁĄTHEM

Grand Crossing, Chicago, IL, 60619

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

About: Hi , My name is Keeshina As a kid Me & my sisters Loves any pet we come in contact with!! My sis has 2 pits 2 cats ...my other a Lil tea cup! I ha... (more)

20. Shellie

Love dogs, owned them for years

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care

"My Pooch was so spoiled during his stay with Shellie...he was so well-taken care of. He's a fiery minpin so I was a little nervous about how he would be wit... (more)"

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Learn About Premier

Dog lovers in Woodlawn, Chicago, IL love dog sitters on Rover.com. Over 7,915 pet owners have reviewed dog sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable dog boarding in Chicago can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Woodlawn dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Woodlawn, Chicago, IL, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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 Woodlawn, 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: