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. Kristal

Your pup's home away from home!

South Deering, Chicago, IL, 60617

Dog Boarding, Doggy Day Care

34 repeat clients

"She's the best. And super flexible with times of drop off and pick up. I'm pretty sure my dog is more excited to see her than she is when she sees me. Great ... (more)"

2. 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)"

3. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

3 repeat clients

"Ruby had such a fun time with Lauren and Bentley! She sent multiple updates throughout the day letting us know how she was doing, which was much appreciated. (more)"

4. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

5 repeat clients

"Gerda was great! My dog has seperation anxiety, so we choose carefully who we leave him with. Gerda made sure to keep me updated throughout the day and our d... (more)"

5. Chas

DOG'S BEST FRIEND -WEEK-DAY SITTING

Lincoln Park, Chicago, IL, 60614

Doggy Day Care, Dog Walking

2 repeat clients

"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)"

6. Rob

A Dog's Favorite Vacation Spot

Near West Side, Chicago, IL, 60606

Dog Boarding, House Sitting, Doggy Day Care

1 repeat client

"Rob and Katie are wonderful pet sitters! They are great with my cats and I trust them anytime I leave town. I just hope that they don't get so popular that t... (more)"

7. 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)

8. Julia

LOVING mom to watch your dog!

Near West Side, Chicago, IL, 60612

Dog Boarding, Doggy Day Care, Dog Walking

About: My daughter and I have a 6 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)

9. 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)"

10. 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)"

11. Nora

love friendly and derpy dogs

Loop, Chicago, IL, 60601

Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Nora was absolutely fantastic with Atticus. They played, went for a long run, played some more - Atticus came home a happy pup. He's in love - Nora is friend... (more)"

12. 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)

13. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney would be an excellent dog sitter. She is a very compassionate person and loves animals. She has watched my dog before, and treated him as if he were... (more)"

14. 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)"

15. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

12 repeat clients

"Bradley did GREAT with Gracie. She came home tired and happy! We're glad she got to socialize with Bradley's pups, and we got constant updates throughout the... (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. Krenare

Your dog will be loved and very well taken care of

Near North Side, Chicago, IL, 60611

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

2 repeat clients

"Linda N. February 26 Keka (Krenare T. ) took excellent care of my little Yorkie Holly. Her apartment is clean, safe, and homey and across from a park. ... (more)"

18. 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)"

19. 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)

20. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

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

5 repeat clients

"I've known Penelope for about a year now, and I consider her a very good friend. She is incredibly caring and kind to everyone around her and that includes a... (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: