Dog Boarding in Oakland, Chicago

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

1. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

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

"Elizabeth and her family took such wonderful care of our 10 month old pup, Bear, while we were away for 5 nights. This was the longest we had ever left him a... (more)"

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2. David Verified Enhanced Background Check

NOT JUST A PET BUT FAMILY

Lower West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Doggy Day Care

"It is such relief knowing your pet will be taken care of in the best hands by David. He kept me updated on how Sam is doing knowing he was a rescue Doberman... (more)"

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3. Matt Verified Enhanced Background CheckRover 101

4 parks within walking distance!

Armour Square, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Matt has been an incredibly loving, reliable and communicative sitter for our dog Dee. He has cared for Dee on multiple occasions and his place feels like a ... (more)"

Active and Accepting Requests (incl. from Essential Workers)
4. Dionne Verified Background CheckRover 101

Furry Friend Extraordinaire!

Woodlawn, CHICAGO, IL, 60637

Dog Boarding, Doggy Day Care

"Dionne is an excellent sitter! She was very thorough tailoring to my dog Penny's needs, professional and prompt in communication, easy and flexible when sche... (more)"

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5. Stanley Verified Background Check

My husky loves energetic friends!

Hyde Park, chicago, IL, 60637

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

About: I have been a dog lover since I could remember! I have had dogs ranging from a small chihuahua to a large cane corso. I currently have a Siberian H... (more)

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6. Kayla Verified Background Check

Dog enthusiast, trustworthy🐶

Near West Side, Chicago, IL, 60607

Dog Boarding, Doggy Day Care

"Kayla is a true professional. She took great care of Sunny. She is compassionate, patient and truly trust worthy, characteristics that make a perfect dog si... (more)"

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7. Andrea Verified Enhanced Background Check

Pet lover with park nearby!

Lower West Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

"Andrea watched my dog Cooper over Christmas. She sent photos of him every day and was great with him. She even picked him up and dropped him off and got him ... (more)"

8. Indy Verified Background Check

Let me love your dog!

Kenwood, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

"Indy was sooooo great with Baxter. She updated me with pictures and videos during my 5 day vacation. It was my first time ever using Rover and Indy walked me... (more)"

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9. Shaley & Melissa Verified Background Check

Friendly petcare by med student duo

Hyde Park, Chicago, IL, 60615

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

"Very communicative and easy to arrange drop off and pick up. Maggie was in good hands and Shaley sent me several picture updates throughout the weekend. Woul... (more)"

10. Janet Verified Background Check

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"Janet was amazing! So great with my dog (who can be difficult sometimes). Winston loves the toy she sent us home with. She was loving, caring and kept me upd... (more)"

Active and Accepting Requests (incl. from Essential Workers)
11. Jen Verified Background CheckRover 101

Home Full-Time - Large Fenced Yard!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"I know Snoop had a great time. Jennifer sent so many photos and messages that were definitely personalized to Snoop. She clearly loves doing this. For the fi... (more)"

12. Waverly Verified Background Check

Soon to be Dr. Wave!

Grand Boulevard, Chicago, IL, 60653

Dog Boarding

"We absolutely love Waverly, and so does our pup! We have used Waverly a few times now. She is responsive and professional. We highly recommend Waverly for yo... (more)"

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13. Victoria Verified Background Check

Especially Fur you!

Near West Side, Chicago, IL, 60606

Dog Boarding, Doggy Day Care

"I wanted to quickly reach out to say how much I really appreciate everything Victoria does for my little furry child. She’s so great with my dog, and I love ... (more)"

Active and Accepting Requests (incl. from Essential Workers)
14. Tamara Verified Background Check

Fun and friendly dog lover ❤️

Near West Side, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Doggy Day Care

"We felt very comfortable leaving our dog with Tammy and would do it again. We got great communication with photos and updates, and we felt completely at ease... (more)"

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15. Monica & Calvin Verified Enhanced Background Check

Dog loving couple in the South Loop

Near South Side, Chicago, IL, 60616

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

"Calvin and Monica took great care of Kali. They sent me lots of updates and photos which made me feel at ease during my trip. Kali looked very happy and had ... (more)"

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16. Michael Verified Enhanced Background CheckRover 101

Always at Home & Right by Dog Park!

Near South Side, Chicago, IL, 60616

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

"Michael was great! They kept in frequent contact and would send me updates of my dog. Will definitely be hiring him again! Highly recommend (: (more)"

17. Kathryn Verified Background Check

Responsible, Energetic Dog Lover

Near West Side, Chicago, IL, 60607

Dog Boarding, Doggy Day Care, Dog Walking

"Kathryn took great care of my pup! I’m especially grateful because he got sick during his stay and she kept me posted on his status throughout the day. (more)"

18. Brian Verified Background Check

5 Year Dog Walking/Sitting Veteran

Logan Square, Chicago, IL, 60647

Dog Boarding

"Brian took a very good care of my two years old husky. I can tell right away when I got back my dog. He is very happy and seems have a wonderful time with B... (more)"

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19. Christy Verified Background Check

My puppy loves playmates

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

"Christy is amazing and so friendly! This was my first time leaving Bailey for more than a weekend away, but I felt very confident she was in excellent hands ... (more)"

Active and Accepting Requests (incl. from Essential Workers)
20. Carol Verified Background Check

Let me spoil your pet(s)

Near North Side, Chicago, IL, 60654

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

"Carol has watch our dog a few times already. She is very helpful and willing to accommodate with your schedule. Our dog has a great time with her while we ar... (more)"

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: