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.
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1. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

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

"Kat is very good dog sitter. My big boy Arrow looks very happy with her. She took him out for a long walk every day! I really want Arrow to continue stay wit... (more)"

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2. Dwight

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

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

"Dwight was an amazing host for our little buddy Arthur! He was communicative and flexible in drop-off and pick-up times, and sent some lovely photo and text ... (more)"

3. Adam

Adam and Caitlin's Pet Care

Near North Side, Chicago, IL, 60611

Dog Boarding

"Adam and his wife were beyond amazing and I would highly recommend their services to any doggie parents out there. Not only did they treat my pup like their ... (more)"

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4. Bridget

I'll love your dog like my own

Near West Side, Chicago, IL, 60661

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

"Bridget is a very attentive and professsional sitter sending regular updates and photos. We felt very comfortable that our Sophie was in very good hands for ... (more)"

5. Elizabeth

Love doggies :) flexible schedule

Lower West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"Without hesitation, we used Elizabeth's services again to take care of our Chihuahua. As expected, she looked after him as if he were her own. Thanks again E... (more)"

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6. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

"Bob took great care of our dog while we were out of town! He gave her a lot of exercise, sent us nice updates, and was very responsive and easy to coordinate... (more)"

Confirmed availability
4th of July
7. Jen & Dakota

Large Fenced Yard and House!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"The best experience for Corcho as always!!!!! Could not leave him with anyone else. Dogs have plenty of time to play and they take such good care of them!!! ... (more)"

Confirmed availability
4th of July
8. Britney

Cozy Home, Large Backyard & LOVE?

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

About: I am FOR SURE an Animal Lover. Growing up with a house full of cats and dogs (even had a ferret) my experience goes back far. I love taking care of... (more)

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9. Christie

Responsible dog handler

Near South Side, Chicago, IL, 60605

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

"Christie took an amazing care of my female goldendoodle, Tofu, while I was gone for 3 days! It was Tofu’s first time boarding with Christie after having gone... (more)"

10. 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)"

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11. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

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

"Alex did a great job boarding my very energetic dog, Gertie. He was flexible, responsive and sent a bunch of great photos. We got back very late so he brough... (more)"

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12. Amber

Downtown dog lover; home full time

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care

"Amber was amazing! Due to an emergency, she had to cancel our booking. That didn't stop her from taking in my pups and working with Rover to find a replaceme... (more)"

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13. Dianne

I can run with your dog!

Armour Square, Chicago, IL, 60616

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

"When it comes to our pups, nothing short of the best care is acceptable. I can assure you, Dianne is the best of them all. Dianne is compassionate, energetic... (more)"

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14. Evan

College student next to dog park!

Near South Side, Chicago, IL, 60605

Dog Boarding, Dog Walking

"Evan was fantastic! We met prior to him having my dog stay and was very responsive. He sent lots of updates and pictures, too. He dropped off my dog and when... (more)"

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15. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Marga did such a wonderful job with our pup! We were out of town for almost 5 days and she attentively cared for our dog and sent regular updates. Our dog, L... (more)"

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16. Susan

I love to run + chill with dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

"Susan is very sweet and accommodating. My older Staffordshire, Maximus, was well taken care of. I recommend Dudan and will definitely use her services again. (more)"

17. Jennifer

I will love your dog as my own.

Hyde Park, Chicago, IL, 60637

Dog Boarding, Doggy Day Care

"I was nervous leaving Lilly with someone I did not know instead of boarding her. When Lilly and I met Jennifer, she was so sweet, kind, and loving towards Li... (more)"

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18. Ekaterina

Home full-time - fenced yard

Bridgeport, CHICAGO, IL, 60608

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

"Ekaterina is amazing with dogs! She is loving and has a great energy that my pups adore. She helped me with occasional walks and extended boarding many times... (more)"

Confirmed availability
4th of July
19. Jenisa

pet lover who works from home

South Side, Chicago, IL, 60653

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

"Jenisa was amazing. Very communicative and kept me updated on how my baby was doing. I know my dog had a blast staying with her! Defiantly found a permanent ... (more)"

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20. Dena

Doggy Spoiler Alert

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Drop-In Visits

"We feel so lucky to have found Dena. Previously, we've boarded our dogs at a northside groomer and they were fine, but it always felt like they were just ho... (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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.