Dog Boarding in Oakland, Chicago

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

1. 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)"

2. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

Dog Boarding

30 repeat clients

"Jessica took great care of Frankie, sent lots of pictures, and gave lots of cuddles. We will definitely be booking his futures stays with her! (more)"

3. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

9 repeat clients

"Cindy treats Armani like her own! She is incredibly sweet to him and sends pictures via text and email often. I feel very comfortable leaving my fur baby in... (more)"

4. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

10 repeat clients

"This was the first time leaving Ruby and I was a mess about it. They were WONDERFUL! We had 3 playdates beforehand meeting with Waffles. Sam and John sent ... (more)"

5. Elizabeth

Dog-lovers in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

"Elizabeth and her husband couldn't have been a more perfect find! We booked them last minute before a weekend trip and they had no problem taking Ollie right... (more)"

6. 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)"

7. 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

"Breana is great! Our dog, Ginger, boarded with her for five days: Breana took the time to meet us and Ginger beforehand, she sent photos to update us through... (more)"

8. Anushi

Home away from home for fur babies

Near North Side, Chicago, IL, 60611

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

1 repeat client

"Anushi was the best!!!!!!! Super friendly and her dog and my dog got along so well. They were best friends for sure. She made sure she understood what Mia ne... (more)"

9. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney was an AMAZING dog sitter! She was very flexible and accommodating with her schedule and she stayed in constant contact with me keeping me up to dat... (more)"

10. 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

"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)"

11. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

3 repeat clients

"Gail was so great with my dog, Oliver. I have a pretty clingy shih tzu and after trying two sitters for him, I thought we just couldn't leave him alone anymo... (more)"

12. Meryl

Animal-loving young professional

Loop, Chicago, IL, 60605

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

1 repeat client

"Mac had such a great time with Meryl! They spent a ton of time at the park and he came back very tired and very happy. And a tired dog is a good dog, so I ... (more)"

13. 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)"

14. Jenna

Dogs best interest always in mind

Loop, Chicago, IL, 60605

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

1 repeat client

"I think Butters made a new friend. Lots of picture updates and response time was fast! (more)"

15. Stacy

Only the Best for Your Furry Bffs

Loop, Chicago, IL, 60605

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

1 repeat client

About: Hi, I'm a recent grad living in South Loop with my goldendoodle. My schedule is somewhat flexible because I work from home a lot. I mostly provi... (more)

16. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

5 repeat clients

"Una had such a great time with Marga! I could tell from all of the much-appreciated photos I received that Una was relaxed, received many cuddles, and enjoye... (more)"

17. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

1 repeat client

"Thunder's stay with Madison was great! Madison and her husband were super hospitable. She sent me pictures every day and it seemed like a fun time all around. (more)"

18. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

2 repeat clients

"Martin watched my 2 large, rambunctious Hound dogs for about a week. He was very friendly, easy to work with, and great with the dogs! I would 110% recommend... (more)"

19. 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)"

20. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (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: