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.
Dismiss
1. Gerda

Professional pet spoiler

Near North Side, Chicago, IL, 60610

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

4 repeat clients

"Belle's first overnight stay. Gerdas was great with her as always. (more)"

2. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

Dog Boarding

28 repeat clients

"Jessica was definitely a find. She was great to work with, punctual, and organized. We received photos and updates every day we were away and Jessica always ... (more)"

3. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

6 repeat clients

"This was our first Rover.com experience, and Cindy's pic message updates were reassuring. We are so glad to find a caring place so close to home! (more)"

4. Megan

Super South Loop Sitters

Near South Side, Chicago, IL, 60605

Dog Boarding

1 repeat client

"I would highly recommend Megan. We met before our stay to ensure that our dogs would get along. Megan sent lots of updates during Mini's stay, which was re... (more)"

5. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

2 repeat clients

"Richard was awesome with Cassie and took very good care of her. He updated me regularly and was open when my flight was late in returning. He sent pictures a... (more)"

6. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

1 repeat client

"Gail was so great with my dog, Oliver. I have a pretty clingy shih tzu and after trying two sitters for him, I thought we just couldn't leave him alone anymo... (more)"

7. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

5 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)"

Confirmed Holiday Availability
8. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

19 repeat clients

"Magdalena was truly a wonderful pet-sitter. From sending us daily pics and updates, to being almost angelically accommodating when our flight was delayed to ... (more)"

9. Sara

Puppy Fever in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

1 repeat client

"Sara did a great job with Sasha and was very flexible in dropping her off. Sasha came home a happy pup! (more)"

10. Andrew

A Dog-Loving New Lawyer

Loop, Chicago, IL, 60604

Dog Boarding, Drop-In Visits, Dog Walking

7 repeat clients

"Andrew did a great job with Cody while I was on an international trip. Before the trip he was extremely responsive in any questions I had and making sure a ... (more)"

11. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

1 repeat client
No Reviews Yet

About: If you need a home away from home for your furry family member contact me today. My family is loving, kind, experienced with animals, and loves dog... (more)

12. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

About: I have owned a dog walking company in LA for over 10 years and we are still going strong. I am looking forward to walking in dogs in my home town. ... (more)

13. Reem

Animal Lover :D :D :D

Loop, Chicago, IL, 60601

Dog Boarding

About: I have two kitties that are basically my children! I am godmother to my sisters dog and spoil her like crazy. Animals are my life and I would love ... (more)

14. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

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

"Samantha is a responsible, caring, genuine person with a big love for dogs. I know Samantha would show love and affection to any animal that she comes across... (more)"

15. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

18 repeat clients

"Elesha was a great sitter for Wyatt and super amenable to our last minute booking. Our dog requires medication twice daily and she was very conscientious abo... (more)"

16. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

17. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

"Mindy was amazing!!! By the looks of the pictures, our dog enjoyed his stay! She sent updates about twice a day which was great! I was glad I left him in the... (more)"

18. Dawn

Choose Dawn! I'm not JUST a soap..

Grand Boulevard, Chicago, IL, 60653

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

2 repeat clients

About: I believe about half of my heart is filled with my love for dogs, the other have is Johnny Depp and Mac and cheese! I've taken care of about 20 dog... (more)

Confirmed Holiday Availability
19. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

"Awesome!! Expert dog handler!! Will use again for sure!! (more)"

20. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"My dogs love and adore LeAnna! As soon as they see her, they jump, slobber and stick to her like glue. She babysat my pups for a week, I totally trusted he... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: