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. Ewelina

Your dog will never feel lonely

Near West Side, Chicago, IL, 60661

Dog Boarding

3 repeat clients

"Ewelina was the perfect sitter for our dog while we were away on a long weekend vacation! She is very friendly and seems to have a true passion for caring fo... (more)"

2. Maribel

M & B Doggy B & B

Chicago, IL, 60632

Dog Boarding

7 repeat clients

"Maribel and Bryan were amazing hosts for Donnie! From the minute we met them, we knew they would take care of him as if he was their own. They were extremely... (more)"

3. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

2 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)"

4. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

10 repeat clients

"Betsey is awesome. Our dog has stayed with her twice and her third stay is already booked!!!! Our dog loves staying with Betsey as made her feel right at ho... (more)"

5. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

4 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)"

6. Amy

Energetic, dog-loving + outdoorsy

Loop, Chicago, IL, 60601

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"She's the best temporary mommy a puppy/dog could ask for. My puppy had the most amazing time with her and her family. She keeps you up to date by sending yo... (more)"

7. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

25 repeat clients

"Samantha was a pleasure from my initial outreach to the time I picked up my dog. I was late dropping her off, but Sam was completely understanding (phew). He... (more)"

8. Deepti

A fun & active home away from home

Near West Side, Chicago, IL, 60607

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

3 repeat clients

"Deepti is a professional and reliable pet care provider. She understood my instructions and had no problems following them. She was always reachable and sent... (more)"

9. Nikki

I am an animal lover to the end.

Woodlawn, Chicago , IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Nikki took great care of my very energetic and sometimes hardheaded puppy Zane. She took him on long walks, which he loves. I'm sure Zane had a great time wi... (more)"

10. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

"Adriana is one of the most responsible people I know. She has taken care of my pets in the past and every time she does I know that I can trust her. She is l... (more)"

11. 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)"

12. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

5 repeat clients

About: I started my pet sitting career with 2 dogs name Eve and Jojo 5 years ago. As soon as I started I fell in love with these 2 babies. Thats when I kn... (more)

13. Brandilyn

Dog Lovers With Fun Doodle

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care, Dog Walking

2 repeat clients

"Brandi and Andy took great care of Mini over a weekend stay. Mini and their dog Winston got along great, and Mini came home happy and tired. :) Brandi sent... (more)"

14. Michelle

Animals are my BFFs

Near South Side, Chicago, IL, 60605

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

1 repeat client

"Michelle was absolutely wonderful! We left Suri with Michelle while we were out of town and she was great about giving us updates throughout the weekend. We... (more)"

15. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

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

"Blaize did a fantastic job with our pups. She watched them for a whole week, and did everything she could to put us and our dogs at ease during that time. We... (more)"

16. Katie

Caring South Loop Dog Lovers

Near South Side, Chicago, IL, 60605

Dog Boarding

"Katie and her husband were super accommodating and friendly. They live in a great area for dog sitting and Izzy seemed to have a great time. Highly recommend. (more)"

17. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

7 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)"

18. Lily

Eager to watch new furry friends!

Bridgeport, Chicago, IL, 60608

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

"Very professional service! Thanks a bunch (more)"

19. 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)"

20. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"Paige watched Portia while we were away for a long weekend. We came back to a happy dog who clearly had enjoyed her time with Paige! Paige sent lots of photo... (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: