Dog Boarding in Oakland, Chicago

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

1. Kaley

Home Full Time! I LOVE PETS!

Near North Side, chicago, IL, 60611

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

5 repeat clients

"Charlie had a great time with kaley and her dog and I would definitely trust her with my dog again! She was very flexible about drop off/pick up/meeting time... (more)"

2. Adam

Adam and Caitlin's Pet Care

Near North Side, Chicago, IL, 60611

Dog Boarding

3 repeat clients

"Adam and Caitlin are AMAZING!! Milo was very spoiled and they sent the cutest pictures and updates. Milo is counting down the seconds until he gets to go ba... (more)"

3. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

11 repeat clients

"Betsey has watched our beagle twice now and she takes such good care of her! She sends us pictures while we are out of town and her schedule allows her to c... (more)"

4. Ryan

Lots of attention and playtime

Loop, Chicago, IL, 60605

Dog Boarding

2 repeat clients

"Ryan was a phenomenal dog sitter! I got photos and updates of Rizzo every day. It also helped that his dog, Butters got along wonderfully with Rizzo. 10/10 r... (more)"

5. Amanda

I'm a student and I love dogs!

Hyde Park, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

"We were very pleased with Amanda's care of our Chihuahua. She was enthusiastic and reliable. We plan to have her watch him again in the future. (more)"

6. Francesca

Fun and Reliable Animal Lover

Loop, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

"Couldn't ask for a better sitter. Truly, personal care attention for Indiana every step of the way. To say that my schedule is difficult, would be putting it... (more)"

7. Elizabeth

Love doggies :) flexible schedule

Lower West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

4 repeat clients

"Outstanding! This is how I would qualify the care our Chihuahua received from Elizabeth. Her love for animals truly shows! Not only Elizabeth provided the ca... (more)"

8. Ray

Less than a block from the park!

Near West Side, Chicago, IL, 60607

Dog Boarding, Doggy Day Care, Dog Walking

About: I have had a dog since I was five years old. It all started with a min pin that I begged for, so I do have experience with small dogs. I have also ... (more)

9. Stacey

South Loop Paw Pad

Near South Side, Chicago, IL, 60605

Dog Boarding

11 repeat clients

"What a great sitter for the South Loop! They clearly take excellent care of their own adorable dog (which says a lot about sitters/people), have a lovely ho... (more)"

10. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding

2 repeat clients

"I was thoroughly please with Ebonee' s skills as a dog sitter, because she went beyond my expectations. Having her as my pet's sitter allowed me to enjoy m... (more)"

11. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

4 repeat clients

"Rebba was awesome!! I received pics and videos of my fur baby throughout the weekend (allowing me to relax and enjoy myself) and when I picked him up, it too... (more)"

12. Alison

Your dog needs a walking partner

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

"Alison was great! Super easy to work with and was so good with my senior dog! (more)"

13. Anquin

Young Dog Friendly Professional

Hyde Park, Chicago, IL, 60637

Dog Boarding

1 repeat client

"Bella enjoyed her stay and really liked playing with Aria. (more)"

14. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

8 repeat clients

"Bob went above and beyond to make sure that our dog was comfortable and happy. He spent a lot of time with her, taking her on more walks than we asked and ev... (more)"

15. Elsa

Dogs are a WOman's best friend.

Lower West Side, Chicago, IL, 60608

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

About: I've had experience with dog walking for about a year and half to two years. I'm currently a student and have a part time job. Whenever I'm not at ... (more)

16. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

8 repeat clients

"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)"

17. Emily

I'll run with your dog!

Hyde Park, Chicago, IL, 60615

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

"Emily did a great job with Clover! She sent some very cute pictures which is a definite plus. (more)"

Available this weekend
18. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

9 repeat clients

"Enoch did a great job watching our English bulldog for the weekend. He was open and flexible on drop off and pick up! And very communicative the entire weeke... (more)"

19. Krystal

Krystal Loves the Pups

Kenwood, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

1 repeat client

"Working with Krystal was an excellent experience. She took great care of our dog and was easy to communicate with before and during the stay. Would definitel... (more)"

20. Hanna

I will give your dog/s lots of hugs

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"I have known Hanna her entire life and what I have observed is what a loving and compassionate person she has grown up to be. She loves animals and is patien... (more)"

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Learn About Premier

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: