Dog Boarding in Oakland, Chicago

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

1. Jennifer Verified Background CheckRover 101

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Stella is super energetic and fun loving which can sometimes make her a handful. Despite that, Jennifer did a great job keeping Stella happy, engaged with to... (more)"

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2. Lisa Verified Enhanced Background Check

Dog walking and sitting!

Near South Side, Chicago, IL, 60605

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

"Lisa was amazing with Wynnie. Wynnie is a bit shy when people excitedly approach her. Lisa was so naturally calming, that Wynnie loved her right away. Seeing... (more)"

3. Jenny Verified Background Check

Dogs bring the best out of me!

Hyde Park, Chicago, IL, 60615

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

"Jenny and Kyle were amazing with my dog :) Leroy had a great time and I could tell he got a ton of extra attention. They were very good about following all o... (more)"

Confirmed availability
Memorial day
4. Matt Verified Enhanced Background CheckRover 101

4 parks within walking distance!

Armour Square, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Matt was great super responsive and send great pictures and updates every day. Also has a great location with a park right in from that our dog loved. Will d... (more)"

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5. Guli Verified Background Check

I love dogs as much as I do my girl

Bridgeport, Chicago, IL, 60616

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

"We had a great experience with Guli. I think she and her young daughter enjoyed having Charlie stay with them, and Charlie enjoyed all the attention he got.... (more)"

6. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Doggy Day Care

"Elizabeth and her family were such wonderful dog sitters. We have a senior dog with special needs, and they took very good care of him, giving him lots of a... (more)"

Confirmed availability
Memorial day
7. Janet Verified Background Check

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Janet was AMAZING with our 15 year old Fifi. Our dog is high maintenance and requires a lot of personal attention. Janet loved on her like she was her own.... (more)"

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8. Sarah Verified Enhanced Background Check

Fit and active dog lover!

Loop, Chicago, IL, 60605

Dog Boarding, Dog Walking

"Sarah was awesome! She was very communicative, polite and patient with Oomber. The pictures of Oomber I got were so adorable and made me feel more comfortabl... (more)"

Confirmed availability
Memorial day
9. Khala Verified Background Check

Always available! Always flexible!

Woodlawn, Chicago, IL, 60637

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

"Khala has been so fantastic. On our 2nd time with her I couldnt drop off Major, and she came to pick him up. He was beyond thrilled to see her!! We are so lu... (more)"

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10. Marga Verified Background Check

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Marga was excellent! She took great care of TJ, was quick to respond to messages, and sent me plenty of updates during his stay. TJ isn’t the friendliest dog... (more)"

11. Jill Verified Background Check

I'll run with your dog

Hyde Park, Chicago, IL, 60637

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

"Jill was great. She offers prompt and regular communication. She is flexible and accommodating to various schedules. She and her husband were kind and patien... (more)"

Confirmed availability
Memorial day
12. Laura Verified Background Check

Dogs are my therapy

Hyde Park, Chicago, IL, 60637

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

"Laura is an amazing person owner! She takes excellent care of her special needs dog, Dante. I've seen them together and he was so loved! (more)"

13. Craig Verified Background CheckRoverGORover 101

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

"We were in Chicago for just a couple of days and wanted our pup to have fun while we were off having fun and boy did he!! When we met Craig and his dogs, my ... (more)"

14. Frank Verified Background Check

They need a break from you anyways

Bridgeport, Chicago, IL, 60616

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

"Frank is a great dog dad. He would be willing to play and entertain your dog whenever you need him to. His strive to make sure a dog is happy is very high. H... (more)"

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15. Ashley Verified Background Check

Open heart and open home..

Kenwood, Chicago, IL, 60615

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

"Ashley was amazing with Betsy! We are so happy we found her last minute. (more)"

16. Shreya Verified Background Check

Pet-lover living in South Loop!

Near South Side, Chicago, IL, 60616

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

"Shreya has been our neighbor for over 6 months. We actually became friends through our dogs! Throughout our relationship with Shreya, she has been a wonderfu... (more)"

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17. Alicia Verified Background Check

Understanding pet’s needs

Washington Park, Chicago, IL, 60637

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

"10/10 would recommend. Alicia is a great sitter. She took such great care of my dog. She was very attentive and a has a great personality. We have been looki... (more)"

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18. Albert Verified Background Check

Missing my 2-y.o. puppy!

Hyde Park, Chicago, IL, 60637

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

"Hojung was perfect. He immediately had a great rapport with Beauregard who is relatively shy, so I had a good feeling right off the bat. He sent many updates... (more)"

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19. Cassidy Verified Background Check

I’ll run with your dog

Hyde Park, Chicago, IL, 60615

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

"Cassidy is a very responsible, attentive, and loving dog caregiver! She grew up with dogs and was their main caregiver - walking, feeding, playing, and taki... (more)"

Confirmed availability
Memorial day
20. Breanna Verified Enhanced Background Check

F/A saving dogs around the world!

Oakland, Chicago, IL, 60653

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

"Breanna was just amazing with our dogs! Sent us updates, pics and even a video. She was very accommodating, and took on two new clients (Sasha and Drexel) fo... (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: