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. Adam

Adam and Caitlin's Pet Care

Near North Side, Chicago, IL, 60611

Dog Boarding

1 repeat client

"Adam and Caitlin did an amazing job taking care of our puppy for the weekend! They sent awesome photo updates throughout the stay and made sure he got plenty... (more)"

2. Tali

Lemon Beagle Mom

Loop, Chicago, IL, 60606

Dog Boarding, Drop-In Visits, Doggy Day Care

"Tali did a great job taking care of Toby. Everything was easy, Toby and I were able to meet her before he stayed by himself, and he was able to get comforta... (more)"

3. Madison

I love to run with dogs!

Near North Side, Chicago, IL, 60654

Dog Boarding, House Sitting, Dog Walking

"Madison was reliable, trustworthy, flexible- and most importantly- so great with our dog who has health needs. Will definitely use her sitter services again (more)"

4. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"Great job and kept me up to date with pictures. She deserves a great, but of course it would be more self serving not to, since people will find what I've fo... (more)"

5. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

10 repeat clients

"Betsey did an amazing job taking care of Vesper for me! She made me feel comfortable and at ease throughout the whole process. I could not ask for a more pos... (more)"

6. Michael

Dog Lover in Loop Neighborhood

Loop, Chicago, IL, 60601

Dog Boarding

"My Pomeranian loves Michael! He has watched her a few times and she immediately lights up and gets very playful when she sees him. Michael is a great dog sit... (more)"

7. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

7 repeat clients

"It goes without say that I would recommend Bob to anyone looking for a caring, knowledgeable, reliable dog sitter. Bob was flexable to my changing schedule, ... (more)"

8. Kaley

Home Full Time! I LOVE PETS!

Near North Side, chicago, IL, 60611

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

1 repeat client

"Where would Sasha and I be without our favorite pet sitter Kaley?! My Siberian husky Sasha is very high maintenance (just like her momma!). When I first adop... (more)"

9. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

3 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)"

10. 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)"

11. Gabrielle

Dog friendly home

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

About: As a student with a dog of my own, I've gone through numerous rounds of various kind of training! From potty training, to simple basic obedience tr... (more)

12. Rebecca

Home full-time - Love being outside

Near South Side, Chicago, IL, 60616

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

"I have never met anyone that loves and cares for dogs as much as Rebecca does! I have had her walk/watch my dogs many times and she is so good with them. A... (more)"

13. Ewelina

Your dog will never feel lonely

Near West Side, Chicago, IL, 60661

Dog Boarding

6 repeat clients

"Ewelina and her boyfriend were excellent carers for our dog, Lola when we left her for a couple of days so we could explore Chicago. Ewelina sent us quite a ... (more)"

14. Taiga

Downtown Apartment w/ Dog Run!

Loop, Chicago, IL, 60601

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

1 repeat client

"Taiga was very accommodating as I had 2 last minute requests to watch my dog. She responds very quickly and is very nice. She sent lots of pics and video... (more)"

15. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

"Our dog received the best care imaginable. We received photo updates and it seems the dog's vacation was enjoyed as much as our own. Five stars! (more)"

16. Dakota

Pet Lover with Large Fenced Yard!

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting

"Dakota and Jen were great with our two small dogs, Teddy and Mojo. They came to our house to meet the dogs and get special instructions for Mojo's diet befo... (more)"

Confirmed available next weekend (Aug 24 - Aug 27)
17. Ebonee

12 + years of Vet-Tech experience!

Hyde Park, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

1 repeat client

"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)"

18. Brittany

My first brother was a Maltese...

Bridgeport, Chicago, IL, 60608

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

"Brittany was very responsive in her communication and took excellent care of our dog. We will definitely be contacting her first if we need care in the future. (more)"

19. Robb

Probably a dog in a past life :-)

Near South Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

1 repeat client

"Robb is the best! He is flexible, wonderful to Rocco I know this because on the 2nd time on our way to Robb's Rocco was a maniac trying to get in his buildin... (more)"

20. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

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

"My dog had a great time. She Looked happy and Blaize sent many photos to show me how comfortable the dog was at her house. I will use her whenever I go out o... (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: