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. Alissa

quality care and a great price!

Near West Side, Chicago, IL, 60607

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

3 repeat clients

"Alissa was great! Lots of video and photo updates during the day - she even took Murphy to the park! He had a blast with her. Thanks again! (more)"

Available this weekend
2. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

5 repeat clients

"Great communication and response to every question I had. Very accommodating. (more)"

3. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care, Dog Walking

8 repeat clients

"Beau had a great time at Lauren's for daycare! He came home exhausted after a day of pestering Bentley so I think he had a great time. He had multiple walks ... (more)"

4. Ariel

Wags and Whiskers!

Lower West Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

21 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)"

5. Anushi

Home away from home for fur babies

Near North Side, Chicago, IL, 60611

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

5 repeat clients

"Our little puppy Theo regularly stays with Anushi. She is so flexible with pick up and drop off times. Theo seems to have so much fun playing at her place. S... (more)"

Available this weekend
6. Priyanka

Priyanka's pooch palace!!

Near North Side, Chicago, IL, 60610

Dog Boarding, Doggy Day Care, Dog Walking

"Hi Priyanka's care of my dog was perfect. She sent pictures and updates unprompted. Definitely would recommend!! I will use her again. (more)"

7. Michelle

Animals are my BFFs

Near South Side, Chicago, IL, 60605

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

1 repeat client

"Michelle was great with Andy! She took excellent care of him and communicating that care to me! (more)"

8. Deepti

A fun & active home away from home

Near West Side, Chicago, IL, 60607

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

3 repeat clients

About: Hi! I'm Deepti, a dog enthusiast, and loving pet sitter :) If your dog likes to play ball, go for long walks, and get lots of rubs and pets, th... (more)

9. Jon

My home is a great place for dogs.

Loop, Chicago, IL, 60601

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

1 repeat client

"Jon would be an amazing Rover sitter! He is responsible, loving, and compassionate in everything that he does. Jon's dedication to animals and their well-bei... (more)"

10. Cristina

Canine Caring by Cris-WFH!

Central, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

6 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)"

11. Richa

Full-Time Dog Mom!! :)

Near South Side, Chicago, IL, 60605

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

1 repeat client

"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)"

12. 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)

13. Lillian

Loves Dogs!

Loop, Chicago, IL, 60607

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

"Lillian is the best! She is responsible and gentle with Pumba. Pumba absolutely loves her. We were not worried at all while we were away and we will not go w... (more)"

14. 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)"

15. Cheryl

full time pet care

Near West Side, Chicago, IL, 60607

Dog Boarding, Doggy Day Care

About: I am home during the day and live next door to a park and a dog park within the park. I am so loving with your dog so they will feel comfortable an... (more)

16. Chornodub

home full time and love animals

Douglas, Chicago, IL, 60616

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

About: Hello, my name is Tia. Why I love animals? 1. They are soooo cute!!! 2. They love you as much as you love them. 3. They are a friend. 4. Anim... (more)

Available this weekend
17. Elizabeth

Home full time, flexible schedule

Lower West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

1 repeat client

"I've never known anyone who's more inlove with animals wellcare than Eli. Honestly, she loves her own dogs and pretty much every dog she sees on the streets,... (more)"

18. Robb

Probably a dog in a past life :-)

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

1 repeat client

"Robb did great with Piper!! He was very easy to communicate with, very flexible, and made my time in Chicago extremely stress free. I would 100% book him aga... (more)"

Available this weekend
19. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

About: My goal as your local pet-sitter/ dog- walker is to raise extra income within my household along with doing something I absolutely love! I'm also l... (more)

20. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"I was traveling out of town for two weeks in January and needed a pet sitter. Rebba was an amazing dog sitter to my beloved Mr. Jinx. She sent me daily photo... (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: