Dog Boarding in Oakland, Chicago

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

1. Tim

Love dogs and the Loop

Loop, Chicago, IL, 60601

Dog Boarding

2 repeat clients

"Absolutely wonderful sitters! Our dog is generally very shy and hesitant with new people, but she got along just great with Tim and his wife! They seemed ver... (more)"

2. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

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

1 repeat client

"Excellent sitter! Samantha is prompt, responsible, and committed. I am very satisfied. She is always welcome to look after my dog. (more)"

3. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

2 repeat clients

"Great stay! Quickly responded to any questions or messages, very accommodating for drop off and pick up times, I got lots of updates and can tell my pup had ... (more)"

4. Grace

Peace. Love. Dog Treats.

Loop, Chicago, IL, 60605

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

1 repeat client

"Grace was super nice and very understanding - we were leaving our Stormy in the late evening with her plus with a very short notice. I will definitely contac... (more)"

5. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

2 repeat clients

"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)"

6. Jessica

Experienced Dog Caregivers & Lovers

Near West Side, Chicago, IL, 60607

Dog Boarding

29 repeat clients

"Jessica and David are amazing! I have three dogs all with unique needs and she was very accommodating. She's a great communicator and sends updates and pictu... (more)"

7. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

7 repeat clients

"Cindy treats Armani like her own! She is incredibly sweet to him and sends pictures via text and email often. I feel very comfortable leaving my fur baby in... (more)"

8. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney watched my 3 year old Yorkie-Dachshund mix and was great! She was flexible and patient with my frequent change of travel plans and made me feel comf... (more)"

9. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

6 repeat clients

"Great stay for Tio. He had plenty of walks and fun with doggie day care visitors. Nice location near a park. Back yard available for scratching his back wi... (more)"

10. Meryl

Animal-loving young professional

Loop, Chicago, IL, 60605

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

"Meryl was the perfect sitter for our dog who suffers from separation anxiety. I am so thankful that I found her and will certainly use her again. (more)"

11. Tatiana

Graduate student who loves dogs!

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"Tatiana was great with my dog Lucy. She was accommodating to our travel situation, concerned when Lucy was not eating because of some anxiety she experienced... (more)"

12. 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)"

13. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

6 repeat clients

"So friendly and flexible with details! She took amazing care of my pup! Would recommend her to anybody and will for sure use Betsey in the future!! (more)"

14. 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)"

15. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

4 repeat clients

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)

16. Stacy

Only the Best for Your Furry Bffs

Loop, Chicago, IL, 60605

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

1 repeat client

About: Hi, I'm a recent grad living in South Loop with my goldendoodle. My schedule is completely flexible because I work at home most times. I can sit ... (more)

17. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits

19 repeat clients

"Buttercup had a fantastic time with Elesha and Troy and we loved getting photo updates while we were away! When we picked her up they had even washed her dog... (more)"

18. Hannah

Professional at loving dogs

Loop, Chicago, IL, 60605

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

"Hannah is a genuine lover of dogs. She is very responsible, caring and just the perfect candidate to watch your pooch. I don't doubt it that Hannah would giv... (more)"

19. 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 matter if you need a dog walker or a dog sitter Martineja is the way to go! I was extremely happy with her fast response and she came with treats and toys... (more)"

20. 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)

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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: