Dog Boarding in Kenwood, Chicago

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

1. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

10 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)"

2. 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)"

3. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

10 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)"

4. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

2 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)"

Confirmed Easter Weekend Availability
5. 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)"

6. 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 did a great job watching Mini overnight. Our dogs got along great and Derick was very flexible with his schedule and coordinating drop off and pick up... (more)"

7. 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

"I would recommend Breana to anyone!! Our 2 year old puppy suffers from separation anxiety. Breanna did everything to make her feel comfortable including feed... (more)"

8. Samantha

Your dogs vacation spot!

Gage Park, Chicago , IL, 60632

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

2 repeat clients

"Samantha was awesome! She watched my two pups over the holiday break and she did an incredible job. She met the dogs in advance and asked about any special... (more)"

9. 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)"

10. 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)"

11. Jenna

Dogs best interest always in mind

Loop, Chicago, IL, 60605

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

1 repeat client

"I think Butters made a new friend. Lots of picture updates and response time was fast! (more)"

12. Meryl

Animal-loving young professional

Loop, Chicago, IL, 60605

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

1 repeat client

"Mac had such a great time with Meryl! They spent a ton of time at the park and he came back very tired and very happy. And a tired dog is a good dog, so I ... (more)"

13. 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)"

Confirmed Easter Weekend Availability
14. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

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

1 repeat client

"Thunder's stay with Madison was great! Madison and her husband were super hospitable. She sent me pictures every day and it seemed like a fun time all around. (more)"

Confirmed Easter Weekend Availability
15. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

2 repeat clients

"5 stars for Martin! Martin took great care of my dog Guthrie over an extended 8-day overnight boarding stay. From the time we spent together I was convince... (more)"

16. 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)

17. Hannah

Dog Sitting in Chicago/West suburbs

Hyde Park, Chicago, IL, 60615

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

"Hannah is great with dogs and loves to be around them. She is an active person so she would be a great person to hire if you want your dogs to be walked and ... (more)"

18. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

"Mindy was amazing!!! By the looks of the pictures, our dog enjoyed his stay! She sent updates about twice a day which was great! I was glad I left him in the... (more)"

19. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

"Lynettra was very kind and my dog Butters was happy with her! :) (more)"

20. Mikayla

Energetic dog-lover

Woodlawn, Chicago, IL, 60637

Dog Boarding, House Sitting, Dog Walking

"Mikayla loves animals, especially dogs. Her fun and cheerful nature attracts dogs to her, and they form an inseparable bond. I couldn't think of a better job... (more)"

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Learn About Premier

Dog lovers in Kenwood, Chicago, IL love dog sitters on Rover.com. Over 7,915 pet owners have reviewed dog sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable dog boarding in Chicago can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you.

Rover.com is the simple, savvy way to find and book Kenwood dog boarding. It's easy to find the perfect dog sitter. Many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book dog boarding on Rover, your dog will enjoy a loving staycation in their sitter's home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter in Kenwood, Chicago, IL has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 75,000 sitters who've listed their services on Rover. When you book Kenwood dog boarding on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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 Kenwood, 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: