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. Ray

Less than a block from the park!

Near West Side, Chicago, IL, 60607

Dog Boarding, Doggy Day Care, Dog Walking

3 repeat clients

"Ray was kind and accommodating. He kept me up to date with Sterling and replied promptly to messages. I would definitely recommend him and would book with hi... (more)"

Confirmed Holiday Availability
2. David

NOT JUST A PET BUT FAMILY

Lower West Side, Chicago, IL, 60608

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

9 repeat clients

About: Hello and thank you for your consideration, my wife (Jennifer N.) and I are both cleared by Rover to provide you our services, when we set up a me... (more)

Confirmed Holiday Availability
3. Somer

Home full-time - live next to a par

Loop, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I am happily married to my best friend. We recently moved to Chicago from Southern California since my husband was transfered for work. We currentl... (more)

4. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

15 repeat clients

"Enoch is energetic, always on his toes when there is a task at hand and is very respectful of other people. He seems to love animals, and often times would e... (more)"

Confirmed Holiday Availability
5. Jessica

Home full time-

Near South Side, Chicago, IL, 60616

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

"Jessica is the best when it comes to reliability and dog care. She has had dogs her whole life and I have never met anyone that loves and cares for dogs and... (more)"

6. Kelly

Doggie care is my life & career!

Near West Side, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Doggy Day Care

"Kelly isn’t just a dog sitter who loves dogs... she is a professional! Studying behavioral issues, working with puppies to get them off on the best foot and... (more)"

Confirmed Holiday Availability
7. Kara

Work from home, love dogs!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

3 repeat clients

"Great experience! Kara sent numerous updates and Hennessy (our dog) had a fantastic time. Would absolutely recommend! (more)"

8. Elizabeth

Love doggies :) flexible schedule

Lower West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

5 repeat clients

"Elizabeth is amazing! She is incredibly responsive and super accommodating. Elizabeth sends pictures throughout the day and takes him on walks and runs! Love... (more)"

9. Rebecca

Home full-time - Love being outside

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

3 repeat clients

"Rebecca is so kind and caring. My dog was in the best mood and slept like an angel after. She got exercise and was very well cared for. My dog requires a l... (more)"

10. Tana

Quiet home with lots of cuddles

Loop, Chicago, IL, 60601

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

6 repeat clients

"Tana is an excellent caregiver, really attentive to my dog's needs and in tune with handling a dog in the city. She has watched my pup for a few daycare sess... (more)"

11. Devon

Active Couple Trying to Fill Void

Loop, Chicago, IL, 60601

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

5 repeat clients

About: Hello! We're Lucas and Devon (pictured; with our friend's dog, Finn!). We are a young (27), active couple that loves dogs of all ages, breeds, and... (more)

12. Ariel

Wags and Whiskers!

Lower West Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

22 repeat clients

"Ariel was great! This was our 4 month old pup's first time away from us and she had a great time. We felt comfortable leaving her with Ariel and look forward... (more)"

Confirmed Holiday Availability
13. Dakota

Large Fenced Yard, Home Full-Time!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

20 repeat clients

"Snickers had such an amazing time! I first felt a little uncomfortable with the whole concept, but they definitely made me feel like I was making a real good... (more)"

Confirmed Holiday Availability
14. Julia

LOVING mom to watch your dog!

Loop, Chicago, IL, 60605

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

5 repeat clients

About: My daughter and I have a 7 year old Shorkie that we have had since she was a puppy. I grew up with dogs and am an animal lover and advocate. I be... (more)

Available this weekend
15. James

Home full-time & love being active!

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care

"Jimmy is the absolute BEST! He took care of my chihuahua, Loquita, for over 10 years and treated her like a princess! I love that he made the effort to vis... (more)"

16. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"Tom would be awesome with your pets! He has had cats and dogs his whole life and could be trusted to take care of them. His pets are happy when he takes them... (more)"

17. Emily

Downtown dog sitter.

Loop, Chicago, IL, 60605

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

1 repeat client

"Great communication! (more)"

Confirmed Holiday Availability
18. Christal

I’m @ home full time

Kenwood, Chicago, IL, 60615

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

About: I love dogs and they love me I have been doing this off and on for years I also had a dog who recently passed away I walked him three times a day a... (more)

19. Richa

Full-Time Dog Mom!! :)

Near South Side, Chicago, IL, 60605

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

4 repeat clients

"This was our first time trying out Rover and we couldn't have been luckier to have Richa take care of our dog over the Thanksgiving holiday. She was incredi... (more)"

20. Yasmine

Ill take runs with your dog

Bridgeport, Chicago, IL, 60608

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

About: Im a dog owner. I like taking care of dogs and i know their needs. Your animal will not miss attenrion. I am a reliable person who appreciates to t... (more)

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: