Dog Boarding in Oakland, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
1. Adam

Adam and Caitlin's Pet Care

Near North Side, Chicago, IL, 60611

Dog Boarding

"Adam and Caitlin did an amazing job taking care of our puppy for the weekend! They sent awesome photo updates throughout the stay and made sure he got plenty... (more)"

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2. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jennifer made us extremely comfortable with leaving our baby behind while we traveled. She sent daily pictures of her am and pm walks along with others that ... (more)"

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3. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

"Craig was great! He really cared to make Princess stay nice. He sent a picture while we were away. Princess was so happy when we picked her up. She really en... (more)"

4. Derryk

Hyde Park Puppy & Dog Sitter

Hyde Park, Chicago, IL, 60615

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

"Excellent sitter for my little one. Very accommodating on pick up and drop off time! (more)"

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5. Ekaterina

Home full-time - small fenced yard

Bridgeport, CHICAGO, IL, 60608

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

"Ekaterina was great! She sent lots of pics of Dolly throughout the stay and was great communicating the drop off / pickup! Dolly really enjoyed the cuddles a... (more)"

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6. Alice

Home full time for your dog(s) solo

Near South Side, Chicago, IL, 60616

Dog Boarding, House Sitting, Doggy Day Care

"Alice and Lee are absolutely fantastic! My poodles have stayed with them twice, and I could tell they were sad to leave both times. They send regular updat... (more)"

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7. Laken

dog lover in downtown Chicago

Loop, Chicago, IL, 60601

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

"Laken took a great care of my 7 year-old golden doodle, Tofu, for three days while I was away on a business trip. She did a wonderful job and kept me posted ... (more)"

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8. David

Caring for other's dogs since 1990

Bridgeport, CHICAGO, IL, 60608

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

"Excellent dog sitter for a last-minute week away! Great with helping to administer meds and providing frequent text updates! Definitely recommend David! (more)"

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9. Jen & Dakota

Large Fenced Yard and House!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"Just picked up Huck yesterday after his first stay with Dakota and am so happy with the service. I got updates and pics every day and Huck seemed very happy ... (more)"

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10. Dwight

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

Dog Boarding, Doggy Day Care, Dog Walking

"Dwight was amazing. He was super friendly and responsive. He took such good care of Gamma and sent us photos that let us know she was having fun in his house... (more)"

11. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

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

"Kat was a fantastic sitter. My dog isn’t always a people person but she cared for him wonderfully. Highly recommend. She updates you with photos every day/ni... (more)"

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12. MK

Former Vet Tech

Hyde Park, CHICAGO, IL, 60615

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

About: I have been involved with many aspects of dog care my entire life. Have a personal affinity for big dogs and absolutely crazy about water dogs. :)... (more)

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13. Lana

Fun and active dog care giver.

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

"Lana did an amazing job with taking care of Simba! I would refer her to anyone as she was very thorough and took the time to ask me particular questions abou... (more)"

14. Kiana

Wags While You're Away

Bridgeport, Chicago, IL, 60616

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

"Kiana is a wonderful and attentive doggy whisperer!! My pups love her and they have so much fun hanging at her place! She takes them on cool adventures and k... (more)"

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15. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

"Bob was awesome! He was easy to communicate with and after the meet & greet I knew my dog, Sebastian, would be comfortable with him. Sebastian spent a week w... (more)"

16. Lisa

Home full-time - lives by dog park

Near South Side, Chicago, IL, 60616

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

"Lisa was a great dog sitter! Very responsive and accommodating, she helped me out last minute during a holiday week. Bok Choy had such a good time with her. ... (more)"

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17. Keziah

Always a fun time!

Near South Side, Chicago, IL, 60616

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

"She is so caring and loves anaimals. She was willing to meet me before I dropped pixie off to let me see where pixie will be staying. Throughout the weekend ... (more)"

18. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

Dog Boarding, Dog Walking

"Alex is great. I have a very shy, timid dog and he extremely patient with him. He kept me updated on how my dog was settling in and let me know once he was ... (more)"

19. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Marga and her roommate took wonderful care of our dog—she sent me daily updates, and they even took him on a mini-hike. We're very grateful to have someone s... (more)"

20. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

"Enoch was just amazing. He was so flexible and accommodating about drop-off/pick-up times. He took wonderful care of my Folly and I could tell she adored him... (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: