Doggy Day Care in Oakland, 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. Alex

Dog lover in downtown Chicago

Near North Side, Chicago, IL, 60611

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

1 repeat client

About: Howdy! My name is Alexander Pinkett, I’m 24 years old, I work as a freelance producer in advertising, I’m resident of Streeterville, and I am witho... (more)

6. Kaley

Home Full Time! I LOVE PETS!

Near North Side, chicago, IL, 60611

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

1 repeat client

"For all the people who know me , they know I don't just let anyone watch my German Shepard and my German Shepard DOES NOT like anyone but me !! Although when... (more)"

7. Kelly

Running through the summer!

Near North Side, Chicago, IL, 60611

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

3 repeat clients

"She is the best!!!! (more)"

8. 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)"

9. Cristina

Canine Caring by Cris-WFH!

Central, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

8 repeat clients

"Christina was great! She was extremely flexible, which made my life so much easier, as I was traveling for work and so much was out of my control. I felt com... (more)"

10. Nicole

The ultimate dog lover!

Near North Side, Chicago, IL, 60611

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

1 repeat client

"Nicole and I have had a dog together for about 8 months now. She is a great caretaker for our dog. We reschedule our pocket pit Cali from the south side of C... (more)"

11. Erin

experienced dog walker

Near North Side, chicago, IL, 60654

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

2 repeat clients

"Erin was the best doggy daycare we could ask for! She was very prompt in her responses to us, was flexible on times and also had a lot of dog items already i... (more)"

12. Hannah

Home full-time dog lover!

Loop, Chicago, IL, 60601

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

About: I am home all day Monday through Friday and my availability on the weekends is very flexible as well! I am also available for dog boarding Sunday-S... (more)

13. 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)"

14. 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)"

15. Katie

Doggy Heaven

Loop, Chicago, IL, 60601

Drop-In Visits, Doggy Day Care, Dog Walking

7 repeat clients

"We were going through Chicago on a road trip and wanted to spend some time in Chicago for the day. Katie took excellent care of our dog Daisy while we were ... (more)"

16. Alissa

quality care and a great price!

Near West Side, Chicago, IL, 60607

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

7 repeat clients

About: I am currently a student at the University of Illinois at Chicago. I grew up with dogs and I miss mine very much while I am away at school. I love ... (more)

Available this weekend
17. 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)"

18. 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)"

19. 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)"

20. 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)"

Experience exceptional service and a personalized match

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

Learn About Premier

Dog owners in Oakland, Chicago, IL turn to day care sitters on 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. Doggy day care can be affordable, no matter where you live or what your price range may be. Curious about how much doggy day care costs in Chicago with Rover.com? Check out our average doggy day care rates near you to get an idea before getting a conversation started with a day care sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

With Rover, you can find a trustworthy, loving pet sitter to take care of your dog while you're at work or have a day full or errands. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 60,000 sitters who've listed their services on Rover. That way, you're sure to find a doggy day care who's right for your needs. We're proud that 95% of our sitters have 100% 5-star reviews, and we think your dog will love them too. Search for a sitter who offers doggy day care, schedule a Meet & Greet, and book the stay if it seems like a good fit. No matter how often you need day care, you're sure to find a sitter who will treat your dog like family. And just like with overnight services booked on Rover, doggy day care is covered by premium insurance, at no extra charge to you.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Oakland, 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: