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

3 repeat clients

"Tim was a great sitter and I'll definitely be reaching out to them next time my pup Nala needs a sitter. He was quick to respond when I reached out last minu... (more)"

2. Meryl

Animal-loving young professional

Loop, Chicago, IL, 60605

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

1 repeat client

"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)"

3. Brandilyn

Dog Lovers With Fun Doodle

Loop, Chicago, IL, 60605

Dog Boarding, Doggy Day Care, Dog Walking

"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)"

4. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Drop-In Visits, Doggy Day Care

8 repeat clients

"I'm so thankful that we now have a reliable, flexible and caring dog sitter! Samantha and John were great from the first meet and greet and pictures througho... (more)"

5. Derick

Any dog is the best kind of dog

Near West Side, Chicago, IL, 60607

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

"Derick is a great guy that's very experienced and knowledgeable about dogs. I would trust and recommend him anytime in the future. Take a leap of faith and b... (more)"

6. 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)"

7. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney was an AMAZING dog sitter! She was very flexible and accommodating with her schedule and she stayed in constant contact with me keeping me up to dat... (more)"

8. Elizabeth

Dog-lovers in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

"Liz and her partner were so wonderful. They were incredibly accommodating and treated our puppy as if she was their very own. They have a wonderful dog thems... (more)"

9. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

3 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)"

10. Jenna

Dogs best interest always in mind

Loop, Chicago, IL, 60605

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

About: I've had a dog growing up and I'm now 22 years old. I'm looking for companionship in college! I don't work, so I have plenty of free time to snuggl... (more)

11. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

5 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)"

12. Nellie

Graduate student who loves dogs :)

Near South Side, Chicago, IL, 60616

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

"Nellie was great! She helped us out when we were in a pinch, and gave Rudy a great vacation while we were away. She gave frequent updates, and when our pup h... (more)"

13. 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)"

Available this weekend
14. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

"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)"

Available this weekend
15. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Breana is great! Our dog, Ginger, boarded with her for five days: Breana took the time to meet us and Ginger beforehand, she sent photos to update us through... (more)"

16. Linda

Clean, happy, fed, and pampered!

Loop, Chicago , IL, 60605

Dog Boarding, Doggy Day Care

"Linda is a wonderful dog sitter. She has raised our maltese terrier, Lucky, for the last 10 years since our family adopted him and she has the most fun with ... (more)"

17. 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)"

18. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

3 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)

19. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

3 repeat clients

"My dog Bella really enjoyed her stay with Martineja. She kept Bella over the weekend and even offered to pick her up since I live along her normal route home... (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)

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: