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. Kaley

Home Full Time! I LOVE PETS!

Near North Side, chicago, IL, 60611

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

7 repeat clients

"Kaley took wonderful care of my nervous dog! I appreciate her patience with him and all the updates and pictures of him enjoying his visit with her. (more)"

2. Elizabeth

Love doggies :) flexible schedule

Lower West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

5 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)"

3. 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)"

4. Jill

Flexible sitting in the SLoop!

Near South Side, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"Jill was great with my dog, Sophie! She was always very responsive and kept me pupdated. We had a meet and greet right away, and two days later she was watc... (more)"

5. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

2 repeat clients

"Alex is an extremely responsible and caring person with great affection for all types of pets. She has taken care of my Westies multiple times over the year... (more)"

6. Laura

Great rates (tail wags included!)

Lower West Side, Chicago, IL, 60608

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

2 repeat clients

"Excellent experience with Laura! I would definitely book her again. (more)"

Confirmed Holiday Availability
7. Dakota

Large Fenced Yard, Home Full-Time!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

20 repeat clients

"Quincy had a fantastic stay with Dakota! We received lots of updates and wonderful pictures throughout his stay. Quincy came home happy and, most importantly... (more)"

8. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding

9 repeat clients

"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)"

9. 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)"

Confirmed Holiday Availability
10. Jessica

Home full time-

Near South Side, Chicago, IL, 60616

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

"Jessica is the best when it comes to reliability and dog care. She has had dogs her whole life and I have never met anyone that loves and cares for dogs and... (more)"

11. Brooke

Brooke's South Loop Services

Near South Side, Chicago, IL, 60616

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

1 repeat client

"Brooke was amazing! My dog loved staying with her and came back very happy. She gave me regular updates and was responsive and accommodating when my flight w... (more)"

12. Rebecca

Home full-time - Love being outside

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

3 repeat clients

"Rebecca took wonderful care of our dog while we were out of town for the weekend. She sent regular updates and pictures, and was very easy to communicate wit... (more)"

13. 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)"

14. Sean

"A dog's best friend"

Hyde Park, Chicago, IL, 60615

Dog Boarding, Dog Walking

"Sean is a very responsible, impersonal and pet-friendly guy who loves animals! He's had a lot of experience with walking and taking care of dogs since we fre... (more)"

15. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

9 repeat clients

"Madison was very responsive and sent lots of great pictures! She is very laid back, easy going, and flexible! Will definitely recommend and use again!! Plus,... (more)"

Available this weekend
16. Henry

Fun, active, friendly grad student!

Hyde Park, Chicago, IL, 60615

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

"Henry was great! He stayed in our house with our energetic standard poodle and both poodle and house were cared for beautifully. Totally recommended. Than... (more)"

17. Dena

Doggy Spoiler Alert

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Drop-In Visits

18 repeat clients

"My dog Simon had a good time with Dena and Sophie. Dena sent nice updates and photos. I was very comfortable leaving Simon with her and would do it again. (more)"

18. Susan

I love to run + chill with dogs!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care

2 repeat clients

"Susan did a great job taking care of my Cohiba! I would definitely book w/her again. She gave me daily updates and sent me pics to assure me he was doing wel... (more)"

19. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

15 repeat clients

"If we could give Enoch six stars we would. There was a last minute scramble to find a sitter and he saved the day. He was very flexible, was willing to stay ... (more)"

20. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

"Kimberlie was a great host for our dog Nola! She sent pics and updates on how Nola was doing and I can tell that she really loves dogs. Kimberlie make the pr... (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: