Doggy Day Care in Woodlawn, Chicago

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

1. Krystal

Krystal Loves the Pups

Kenwood, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"I have known Krystal for going on a decade and she has always been extremely ethical and compassionate. Krystal has always gone out of her way to help others... (more)"

Available this weekend
2. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

1 repeat client

"I can not say enough about Ebonee! She is totally amazing! She took such good care of Milo and sent pictures and videos of his stay with her. She is respons... (more)"

3. Rebecca

Home full-time - Love being outside

Near South Side, Chicago, IL, 60616

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

"I have left my dog with Rebecca several times and have been impressed every time! She creates a very comfortable environment for Milo to relax in and plays w... (more)"

4. Yvonne

Greyhound Mom: Loving Sitter/Walker

Lower West Side, Chicago, IL, 60608

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

"Yvonne was wonderful! I knew Watson was in good hands as, when I came to pick him up, he kept rushing back to Yvonne for another snuggle before we left. We'l... (more)"

5. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

37 repeat clients

"Kristal is fabulous. My puppy really enjoyed his time at her home. By the time I would pick up my puppy he would be so exhausted from all the fun he had with... (more)"

6. Ariel

Wags and Whiskers!

Lower West Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

22 repeat clients

"Ariel is a sweetheart and connects with your dog like it's her own! It was my first time leaving our 3mo puppy with someone for daycare, and I can't say enou... (more)"

7. Richa

Full-Time Dog Mom!! :)

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"We used Richa for dog day care and she was great! Our dogs got along great (Soni is a sweetheart!) and our dog always came home exhausted from play. Richa di... (more)"

8. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

6 repeat clients

"Madison and her family were great! I had a last minute request and they were flexible and ready to go. Lily really enjoyed her stay. (more)"

Available this weekend
9. Nathalia

Caring for your dog like family!

West Lawn, CHICAGO, IL, 60629

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

"My sister evelin is extremely passionate about caring for animals specially dogs! She has 5 years of experience caring for dogs and cats and always get amazi... (more)"

Available this weekend
10. Dakota

Pet Lover with Large Fenced Yard!

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting, Doggy Day Care

"Dakota is a dependable dog sitter, he has watched my dogs for over 2 years now. He comes over at set times to walk, exercise and feed them. I would highly ... (more)"

11. 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 was great! She was flexible with her schedule/specific arrangements, very responsive to my messages, took my pup running, and sent me updates throughou... (more)"

12. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"Jeannette M Tom has been a caregiver for our beagle, Boomer. He walked, talked and ran with him. I trust him with all my pets! (more)"

13. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

3 repeat clients

"Gail sat for my dog on many different occasions over the years and she always does an amazing job. She is extremely detailed oriented and makes sure she kno... (more)"

14. Iris

LG Fence yards, parks/beach,cuddles

South Side, Chicago , IL, 60617

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

About: Hello! I have grown up with animals my entire life. Starting out with cats, dogs, lizards and fish, I also took interest in exotic animals such a... (more)

Available this weekend
15. Brittany

My first brother was a Maltese...

Bridgeport, Chicago, IL, 60608

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

1 repeat client

"Brittany has a magical way with dogs, cats rats, snakes, and plants. She has watched all my pets and is very skilled, caring and patient. She's also excellen... (more)"

16. Keeshina

PETS ARE HUMANS IN DIFF.FORMS ❤THEM

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)

17. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

3 repeat clients

"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)"

Available this weekend
18. MICHAIAH

Ready for Your Rover!

Chatham, CHICAGO, IL, 60619

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

About: I love animals and they love me. I'm very loving and my space is pet friendly! Pit bulls are my favorite and I enjoy the company. I always wanted m... (more)

Available this weekend
19. Aaliyah

Dog Care Chicago

Grand Crossing, CHICAGO, IL, 60621

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

About: A true mommy dog lover.I have 2 small Maltese Poodles. Going away for the weekend or Holidays. Allow me to take care of your baby like my own. I ... (more)

20. Jennifer

I'll love to meet your furry family

Grand Boulevard, Chicago, IL, 60615

Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi !!! I'm Jen. I am a previous pet owner. King, our Pit/Boxer. He stood almost 3 feet and was a joy. We have him to loving family, that could pro... (more)

Experience exceptional service and a personalized match

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

Learn About Premier

In Woodlawn, Chicago, IL, dog lovers trust Rover.com for their doggy day care needs. Over 7,915 pet owners have reviewed day care sitters in Chicago, giving them an average rating of 4.9/5 stars. Booking doggy day care in Woodlawn can be incredibly affordable, no matter what price range you're looking for. Curious about what it might cost to book doggy day care in Chicago on Rover? Check out our average doggy day care rates to get an idea before reaching out and beginning a conversation with a sitter.

Don't let your 9-to-5 stop you from being a great pet parent. When you're heading to work, drop off your beloved pet with a loving dog sitter in Woodlawn, Chicago. Your dog will get the love and care they're used to at home, and you'll get photo updates and the peace of mind that comes from finding great care for your pet. We're proud to offer a wide range of pet care, including puppy day care and pet day care for all kinds of pets. We know you love your pets, but you can't always be there, which is where our loving sitters come in. Forget kennels, find a loving neighbor who will give your dog the one-on-one attention they deserve. That way, when you head to work, you know your dog's in good hands.

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: