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. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jennifer was great! She met with riggins beforehand to make sure they were a good fit, and cared for him like he was her own. She was so sweet and sent me pi... (more)"

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2. Khala

Always available! Always flexible!

Woodlawn, Chicago, IL, 60637

Dog Boarding

"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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3. Janet

Lakefront, parks, beach & dog park

Hyde Park, Chicago, IL, 60615

Dog Boarding

"Janet has sat many times for my dog both in her home and in mine. Janet is responsible, trustworthy, and loves dogs. Most importantly, she provides loving ... (more)"

Confirmed availability
Christmas and New Year
4. Terry

I love dogs and Love to be outside

Near South Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Terry was quick to respond and was wonderful with our big, energetic boy. I couldn’t be more pleased with the whole stay. (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 with Harper! My dog has alot of energy and Ekaterina kept her busy and played with her. She sent several photos which put my mind at ease... (more)"

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6. Joanne

Dog Mom, Rescue Volunteer & Foster

Loop, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Doggy Day Care

"Joanne did a wonderful job taking care of Dominic while I was out of town! She provided plenty of pictures and updates, and went the extra mile to ensure he ... (more)"

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7. Catherine

I’ll nurture your furry best friend

Hyde Park, Chicago, IL, 60637

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

"Catherine was lovely to work with. She provided excellent care of Freddy, and even did a little training with him. She really tried to accommodate his indivi... (more)"

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8. Natalie

Long time owner first time walker

Loop, Chicago, IL, 60605

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

"Natalie likes dogs and has a nice, calm, confident manner that inspires trust. She is also responsible and dependable. I would trust her with my favorite fur... (more)"

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9. Presley

lifelong pet owner; home full-time

Near South Side, Chicago, IL, 60605

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

"I can not think Presley enough for taking care of my sweet Braxton. She went above and beyond to make sure he was comfortable in her home. She loved on him,... (more)"

Confirmed availability
Christmas and New Year
10. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

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

"Britney loves all kinds of dogs. She enjoys their company as much as they enjoy hers. She would be a great asset to your company. (more)"

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11. Saroja

Work from home; dog run in building

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

"Saroja was a great sitter for my pup! She was very easy to get in touch with, sent routine updates and pictures upon request, and most importantly made my d... (more)"

Confirmed availability
Christmas and New Year
12. Jen & Dakota

Large Fenced Yard, Home Full-Time!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

"Jen and Dakota were amazing with Melvin, he had tons of fun with the other pups and enjoyed his stay so much! We’ll definitely book them again, we’re so grat... (more)"

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13. Kirste

Fred Anderson Dog Park next door.

Near South Side, Chicago, IL, 60616

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

"Kirste is awesome! She totally got Beaubert and they bonded right away! She was very flexible in meeting us and sent updates throughout the weekend of how th... (more)"

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14. Jasmine

Plenty of long walks and treats!

Bridgeport, Chicago, IL, 60609

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

"My dog, Willow, seemed to enjoy staying with Jasmine, and everything seemed to go well. Jasmine sent photos during those few days we were gone. I would rec... (more)"

Confirmed availability
Christmas and New Year
15. Heather

Work from home - Dog Park in back!

Near South Side, Chicago, IL, 60616

Dog Boarding

"Heather was amazing! She sent lots of pictures and updates at least once a day, sometimes more. My puppy got along well with their dog Lucy, and actually c... (more)"

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16. Kiana

Wags While You're Away

Bridgeport, Chicago, IL, 60616

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

"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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17. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

"oli loved his stay. marga and kate were so wonderful and patient w oli. he looked so content and cozy in the pics we got. i would 100% recommend and rebook! (more)"

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18. Zak

Home all day - fenced yard

Douglas, Chicago, IL, 60616

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

"Zak did an amazing job with Golfo! He sent me a lot of pictures and always updated me on what they were up to! I’m sure golfo had a lot of fun and I would to... (more)"

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19. Irema

The most attentive doggo lover

Hyde Park, Chicago, IL, 60637

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

"I have known Irema since high school and she is an amazing dog owner and caregiver. She is always excited to help dogs feel special and loved. Irema board... (more)"

Confirmed availability
This weekend
20. Cassidy

I’ll run with your dog

Hyde Park, Chicago, IL, 60615

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

"Cassidy grew up on a dairy farm and has cared for a variety of animals - from millipedes to cows! She has always lived with dogs and cats and has an uncanny... (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: