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. Erica

Wags While You're Away!

West Town, Chicago, IL, 60642

Dog Boarding, Drop-In Visits

75 repeat clients

"Erica is very literally a dream come true as a dogsitter. She genuinely cares for each and every dog that she agrees to sit. She never takes too many. She pa... (more)"

2. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

"Rebba was awesome!! I received pics and videos of my fur baby throughout the weekend (allowing me to relax and enjoy myself) and when I picked him up, it too... (more)"

3. Mandi

Love Pups!

Central, Chicago, IL, 60654

Dog Boarding

6 repeat clients

About: Hi! I am an active young professional who loves dogs! I grew up with our family dog who lived for 18 years and definitely miss having a furry frie... (more)

4. Kameron

Stay & Play in the Loop with a View

Chicago Loop, Chicago, IL, 60601

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

1 repeat client

About: **About me** Hi! I'm Kameron and would love to hang out with your dog in the Loop! I love the location I live in because I am extremely close to Mi... (more)

5. Natasha

Your Puppy's Home Away from Home!

Near North Side, Chicago, IL, 60611

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

15 repeat clients

About: Hey there, We're two super responsible medical students with a love for animals! We currently have a lot of time on our hands, as we're mostly a... (more)

6. Amy

Energetic, dog-loving + outdoorsy

Loop, Chicago, IL, 60601

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

"Amy was an incredible dog sitter for my pup Mila! I received pictures every few hours, and Amy would take them on long walks multiple times through out the d... (more)"

7. Brandilyn

Dog Lovers With Fun Doodle

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care, Dog Walking

1 repeat client

"Brandi and Andy were fantastic hosts to our dog Timon, and get our highest recommendation. Timon was very happy when we picked him up after a weekend full of... (more)"

8. Ewelina

Your dog will never feel lonely

Near West Side, Chicago, IL, 60661

Dog Boarding, House Sitting, Doggy Day Care

1 repeat client

About: **About me** I've been around dogs mostly my whole life. Growing up in Poland I had all sorts of animals around me. My dog, Stanley is very frien... (more)

9. Robert

All furry friends welcome!

Loop, Chicago , IL, 60601

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

12 repeat clients

"Robert was a lifesaver! It was such a last minute booking for dog boarding and out of a bunch of sitters, I found him. He is very accomodating and genuinely ... (more)"

10. 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)"

11. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, 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)"

12. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

1 repeat client

About: A lifetime of experience with multiple dogs and friendly felines, I love both and am here to provide loving care and attention to your furry pet wh... (more)

13. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Drop-In Visits, Doggy Day Care

24 repeat clients

"Samantha was great to work with, and her own dog, Waffles, is very cute and friendly. Samantha took careful notes about our pup's schedule, habits, and medic... (more)"

14. 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)"

15. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

7 repeat clients

"Marga took care of both my dogs Max and Nala during last weekend. I am 100% happy with her. She was extremely attentive to the instructions I gave (I am a bi... (more)"

16. Stacey

South Loop Paw Pad

Near South Side, Chicago, IL, 60605

Dog Boarding

10 repeat clients

"Stacey has a way with dogs that is almost magical, certainly worthy of admiration. I trust her completely with my babies, one of which is a very senior dog. ... (more)"

17. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

3 repeat clients

"Madison and her family were wonderful hosts to my dog! (more)"

18. kimberlie

Hyde Park Pawadise!

Hyde Park, Chicago, IL, 60615

Dog Boarding

17 repeat clients

About: Hi all, my name is Kimberlie and I have grown-up with dogs & truly just love all different sizes & personalities!! Life is better with a pooch :) W... (more)

19. 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)"

20. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"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: