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. Stacy

Only the Best for Your Furry Bffs

Loop, Chicago, IL, 60605

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

About: Hi, I'm a recent college grad living in South Loop with my goldendoodle. My schedule is completely flexible because I work at home most times. I ... (more)

2. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

4 repeat clients

"Gerda was so great with our sweet Belle! This was the first time I had to find a dog sitter and I would trust Belle with Gerda at any point in time again! Th... (more)"

3. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

29 repeat clients

"Kristal was very flexible and had responded to my text very quickly. We've had horrible expierences with sitters once we got King back, Acting funny or not ... (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. 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

"Kylie is so great with my dog. Her home and Miles provide a perfect place for play and entertainment. Kylie went out of her way to help us on a rainy day. ... (more)"

6. Chas

DOG'S BEST FRIEND -WEEK-DAY SITTING

Lincoln Park, Chicago, IL, 60614

Doggy Day Care

"Chas was really helpful and we enjoyed receiving pictures throughout the day. She seemed really happy after her day of fun. Will definitely re-book in the fu... (more)"

7. Nora

love friendly and derpy dogs

Loop, Chicago, IL, 60601

Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Nora was amazing! She was super flexible with my weird schedule, always friendly, and prompt to respond. Nora took great care of my Cali while I was away and... (more)"

8. 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)"

9. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

1 repeat client

"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)"

10. Rob

A Dog's Favorite Vacation Spot

Near West Side, Chicago, IL, 60606

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

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)"

11. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

12 repeat clients

"Another wonderful stay with Bradley! My puppy has so much fun and gets good socialization and exercise with Bradley. I appreciate his flexibility on drop o... (more)"

12. 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)"

13. 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)

14. 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)"

15. Robbie

animals may think I'm dr Doolittle

Kenwood, Chicago , IL, 60615

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I have experienced small and large dogs throughout my life and I'm in love with animals. I treat animals as if their my children. I hate to see any... (more)

16. Richa

Loving couple who love pets!!

Near South Side, Chicago, IL, 60605

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

About: My husband and I are home most of the time with our puppy if we are not at the dog park. Our little pup loves to play and would love to have a slum... (more)

17. Hailey

Join the puppy party!

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

"Hailey is a caring and compassionate person who loves pets She is a fantastic pet owner and I would highly recommend her! She will treat the pet as her ow... (more)"

18. Keeshina

PETS ARE HUMANS IN DIFF.FORMS ÔŁĄTHEM

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)

19. Ruth

Let's have a fun day!!

Near West Side, Chicago, IL, 60607

Doggy Day Care

About: Hi there! Are you looking for a fun friendly place where your love one can have a great time? You find it! Sprinkles and I will be your dog best fr... (more)

20. Dawn

Choose Dawn! I'm not JUST a soap..

Grand Boulevard, Chicago, IL, 60653

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

2 repeat clients

About: I believe about half of my heart is filled with my love for dogs, the other have is Johnny Depp and Mac and cheese! I've taken care of about 20 dog... (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: