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. 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)"

2. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

6 repeat clients

"Gerda and her roommate is amazing. Their room is safe and beautiful and there is a nearby walking distance park that dogs can walk whenever. They are kind, u... (more)"

3. Chas

DOG'S BEST FRIEND -WEEK-DAY SITTING

Lincoln Park, Chicago, IL, 60614

Dog Boarding, Doggy Day Care, Dog Walking

4 repeat clients

"Chas is the best! He watches my dog, Cocoa Bella, often and she absolutely loves him. He is also super professional and always willing to work with Cocoa and... (more)"

4. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

3 repeat clients

"My puppy loved playing all day with Lauren and her dog. They became fast friends and she update me with adorable photos. I will definitely rebook with Lauren... (more)"

5. Rob

A Dog's Favorite Vacation Spot

Near West Side, Chicago, IL, 60606

Dog Boarding, House Sitting, Doggy Day Care

1 repeat client

"Rob is superb with my dog as I am sure he is with every dog he cares for. He seems to understand my dog's needs and wants. But at the same time, Rob doesn'... (more)"

6. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"We want you to know that Courtney S. absolutely will love on your precious fur babies just like she does with her Trixie. Do not hesitate for a minute when y... (more)"

7. Kylie

Flexible days/hours dog care

Near North Side, Chicago, IL, 60654

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

2 repeat clients

"Kyle is so accommodating and great and I have been nothing but pleased with my experience thus far and will continue to have her watch my puppy! She has also... (more)"

8. Derick

Any dog is the best kind of dog

Near West Side, Chicago, IL, 60607

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

About: From an early age I always had an intrest and love for ldogs, I constantly expanded my knowledge regarding dogs and how to properly raise them. On... (more)

9. Alex

Every Dog Has Its Day in RiverWest!

West Town, Chicago, IL, 60654

Dog Boarding, Doggy Day Care

1 repeat client

"Alex is one of the most organised and friendly people I know! He is a true animal lover and with a big heart, he is generous to everyone. I cannot recommend ... (more)"

10. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

About: Hi, I'm Lyn. I am a pet care professional and an animal lover. I have a passion for pet care and have been in the field 5+ years. With my passion, ... (more)

11. Katie

Doggy Heaven

Loop, Chicago, IL, 60601

Drop-In Visits, Doggy Day Care, Dog Walking

6 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)"

12. Sara

Puppy Fever in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

1 repeat client

"Sara has taken care of my 2 Maltese poodles several times. She has stopped in to feed and walk them when we are unable to get home from work on time as well... (more)"

13. Linda

Clean, happy, fed, and pampered!

Loop, Chicago , IL, 60605

Dog Boarding, Doggy Day Care

"Linda is absolutely great with my pup! He is always excited to see her. She is also very flexible when it comes to making arrangements. (more)"

14. Richa

Loving couple who love pets!!

Near South Side, Chicago, IL, 60605

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

"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)"

15. Jenna

Dogs best interest always in mind

Loop, Chicago, IL, 60605

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

About: I've had a dog growing up and I'm now 22 years old. I'm looking for companionship in college! I don't work, so I have plenty of free time to snuggl... (more)

16. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

1 repeat client
No Reviews Yet

About: I started my pet sitting career with 2 dogs name Eve and Jojo 5 years ago. As soon as I started I fell in love with these 2 babies. Thats when I kn... (more)

17. Vanessa

Fun caring dog lover.

Near North Side, Chicago, IL, 60654

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

6 repeat clients

About: We moved from Costa Rica last year and we love Chicago and its dog friendly parks. I've been a dog owner and lover since I can remember (I also lik... (more)

18. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

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

7 repeat clients

"Danielle stepped in at the last moment when another sitter had canceled on us, and she took great care of our dog Kaiser. She was especially accommodating ab... (more)"

19. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

12 repeat clients

"Bradley was awesome and my dog had a wonderful time in his care. He sent me videos and pictures throughout the day, he was having such a good time I wasn't s... (more)"

20. Dana

Hyde Park Animal Sitter for Hire!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

2 repeat clients

"Dana is a great dog sitter!! She loves animals and is very patient with them. She treats them like they are her children. She's a very responsible and lovin... (more)"

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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: