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. Elizabeth

Home full time, med fenced yard

North Lawndale, Chicago, IL, 60623

Dog Boarding, Doggy Day Care

"Liz is fantastic! She has watched my dog in the past and took such great care of him. I have an greyhound with a ton of energy and she did such a great jo... (more)"

2. Anushi

Home away from home for fur babies

Near North Side, Chicago, IL, 60611

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

3 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)"

3. Joe

Lover of all dogs! Allergic to cats

West Town, Chicago, IL, 60622

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

3 repeat clients

"Joe was amazing with my dog. I'd never left him with anyone other than my parents before. Joe watched him for several nights and was a natural. His love for ... (more)"

Available this weekend
4. Robert

All furry friends welcome!

Near North Side, Chicago , IL, 60654

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

10 repeat clients

"Robert was great with my pup! We met beforehand and he answered all of my questions. He was very flexible when traffic impacted the pick up time. My pup came... (more)"

5. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

3 repeat clients

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

6. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

5 repeat clients

"Lauren was awesome! Riley was super happy when I picked her up and lauren updated me all day and sent the most adorable pics. We will definitely be booking h... (more)"

7. Dominique

Love given, Love needed, Love dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

"Dominique Higgins loves dogs and would make a great sitter. She is a very cheerful person with alot of energy and patience which makes her the perfect pet s... (more)"

8. 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)"

9. Michelle

Dogs are my light of this world.

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)"

10. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

7 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)"

11. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

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

About: I am very easy to talk to and communicate with. I would say that I am quite nice and easily approachable. I will watch dogs and cats as well as oth... (more)

12. Ellen

Safe, Reliable and Loving Dog Care!

Near West Side, Chicago, IL, 60608

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

1 repeat client

"Ellen is extremely kind, energetic, and responsible. She is a natural with dogs (and animals in general); she shows our animal friends an abundance of love ... (more)"

13. Stephanie

I can't wait to meet your pup!

Near North Side, Chicago , IL, 60654

Dog Boarding, Doggy Day Care

"Experience with Stephanie could not have been better; she was very responsive to messages, sent updates about Lincoln's stay, and Linc had a blast playing wi... (more)"

14. Hilda

Loving & caring family environment.

Brighton Park, Chicago, IL, 60632

Dog Boarding, Doggy Day Care, Dog Walking

5 repeat clients

"I have known Hilda for over 5 years and it doesn't surprise me when she is walking down the street and she stops to say something nice to a dog. She says thi... (more)"

15. 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)"

16. Richa

Loving couple who love pets!!

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)"

17. Amy

Energetic, dog-loving + outdoorsy

Loop, Chicago, IL, 60601

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

"Amy loves "fur" friends. I highly recommend Amy as a great care giver for your 4-legged family members. She has a huge respect and a deep understanding of ... (more)"

18. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"Jeannette M Tom has been a caregiver for our beagle, Boomer. He walked, talked and ran with him. I trust him with all my pets! (more)"

19. Cortney

Work-From-Home Gal with Pekingese

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care

About: My name is Porter, and my mommy, Cortney, works from home when she is not traveling. I'm a 7 year old male Pekingese and I love having doggie visi... (more)

20. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

"Rebba is incredibly compassionate and loving with dogs. She genuinely cares for them and showed great kindness and care for my late dog. Your dog will be i... (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: