Dog Boarding in Oakland, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

1. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

12 repeat clients

"Samantha & her husband did a fantastic job watching my pet! During the meet & greet she asked all the right questions and made it clear they're familiar with... (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

"My puppy Finch had a wonderful time staying with Anushi! I was nervous at first leaving him for 5 nights, because we hadn't spent any time apart - but Anushi... (more)"

3. 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 was so wonderful to my Bailey! She took Bailey for long walks and sent me many pictures while I was away. Ellen was very accommodating, extending the s... (more)"

4. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

2 repeat clients

"Richard was awesome with Cassie and took very good care of her. He updated me regularly and was open when my flight was late in returning. He sent pictures a... (more)"

5. Andrew

River North Pooch Pros!

Near North Side, Chicago, IL, 60654

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Andrew went above and beyond in watching my little guy Rufio. He took great care of him and I got daily updates about their trips to the dog park and endless... (more)"

6. Brandilyn

Dog Lovers With Fun Doodle

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care, Dog Walking

"Love Brandi. Hated being away from my pooch so she sent me a lot of pictures of him looking a little too happy in her home :) I ended up in the hospital and ... (more)"

7. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"Courtney watched my 3 year old Yorkie-Dachshund mix and was great! She was flexible and patient with my frequent change of travel plans and made me feel comf... (more)"

8. Samantha

My friends call me a Dog Whisperer.

Near West Side, Chicago, IL, 60607

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Samantha was great! She was super responsive to messages and sent daily pictures of my dog while I was away. She was also very flexible with pick-up and drop... (more)"

9. 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

1 repeat client

"Derick did a great job watching Mini overnight. Our dogs got along great and Derick was very flexible with his schedule and coordinating drop off and pick up... (more)"

10. 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)

11. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

8 repeat clients

"Toby had a great time with Betsey and I could enjoy my vacations knowing that my puppy was good. I got a lot of pictures and messages everyday. I will recomm... (more)"

12. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

6 repeat clients

"Marga took care of both my dogs Max and Nala during last weekend. I am 100% happy with her. She was extremely attentive to the instructions I gave (I am a bi... (more)"

13. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

"Rebba was awesome!! I received pics and videos of my fur baby throughout the weekend (allowing me to relax and enjoy myself) and when I picked him up, it too... (more)"

14. Meryl

Animal-loving young professional

Loop, Chicago, IL, 60605

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Meryl was an excellent sitter for my pooch, Jax! Her excellent communication and response times made me feel at ease. She took him to the park often to play... (more)"

15. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

3 repeat clients

"Madison and her family were wonderful hosts to my dog! (more)"

16. 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

About: I love dogs, I have been taking care of other people's dogs for years. Whether it is a close friend of family member, taking care of dogs is not ju... (more)

17. Harrison

Responsible dog-loving professional

Near South Side, Chicago, IL, 60605

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Harrison was great. Such a nice guy and really took time to understand what my dogs needs were and my dog was clearly comfortable with him. He took photos... (more)"

18. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"I would recommend Breana to anyone!! Our 2 year old puppy suffers from separation anxiety. Breanna did everything to make her feel comfortable including feed... (more)"

19. Lily

Eager to watch new furry friends!

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Very professional service! Thanks a bunch (more)"

20. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Paige watched Portia while we were away for a long weekend. We came back to a happy dog who clearly had enjoyed her time with Paige! Paige sent lots of photo... (more)"

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Learn About Premier

Pet parents turn to sitters on Rover.com when they're looking for overnight boarding for their dog. 7,915 owners have reviewed sitters in Oakland, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect dog sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average dog boarding rates to get an idea before you start a conversation with a dog sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Oakland dog sitter in seconds on Rover.com. If you're looking for dog boarding while you're away, whether it's for one night or a whole month, you can find a dog sitter in Oakland, Chicago, IL who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks and community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers for hire, and that includes offering pet boarding in Oakland.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. 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: