To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed Labor Day Availability
1. Frank

Play date with the boys!

South Lawndale, Chicago, IL, 60608

"Frank did an awesome job with our dog Napolean! He communicated everyday through updates and wonderful pictures. He was very friendly and professional. T... (more)"

2. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

"This was my first time using Rover. Mags did an awesome job watching redd. She updated me with pictures through out his week stay. He looks comfortable and... (more)"

3. Katie

Two humans and a beagle

Near South Side, Chicago, IL, 60605

"Katie is fantastic with dogs! As a dog-lover myself, it's very important to me to know that anyone I have dog-sit will treat my dog as well as I do: that's K... (more)"

4. Janina

Dog Loving Home

Near West Side, Chicago, IL, 60612

"I absolutely love her! She sent me pictures throughout the visit! I also had to extend the visit and she made accommodations for us without an issue! Puff lo... (more)"

Confirmed Labor Day Availability
5. Gabriel

MedStudent Spoils Pups,NoStairs4Old

Near West Side, chicago, IL, 60612

"Gabriel was available for our last minute request. My little girl "Baby" was comfortable and I was happy. Thanks Gabriel! (more)"

6. Maria

Your Loved One's Second Home

Loop, Chicago, IL, 60605

"Maria asked great questions and was quite prepared for our meet and greet. She sent us wonderful photos and kept us up-to-date of how the pooch was doing. He... (more)"

7. Lor'Enyah

Chi-City Pet Co.

Lower West Side, Chicago, IL, 60608

"Lor'Enyah sent lots of pictures of Gracie having a good time and going on doggy play dates. It was pretty hot and she even took her for a dip in the doggy po... (more)"

8. Nicky

Pet Friendly home, loves dogs!

Near North Side, Chicago, IL, 60611

"Nicky was great with my little guy! She sent me pictures, videos, and updates all weekend! He had so much fun he was exhausted by the time i got him home! ... (more)"

9. Risa

Stay at home puppy mom - Dawg House

Near West Side, Chicago, IL, 60607

"This is our first try on and this experience with Risa was completely fantastic. Risa,Matt and Addison gave us a warm welcome and led us to their s... (more)"

10. Jennifer

Dog Sitter Extraordinaire

Bridgeport, Chicago, IL, 60608

"Jennifer was a fantastic sitter for our energetic Great Pyrenees! She was genuinely excited for Bauer's stay which made it easier to drop him off. She se... (more)"

Confirmed Labor Day Availability
11. Rohit

Reliable & Responsible

Near West Side, Chicago, IL, 60661

About: I've been around dogs all my life in one form or another and have a strong connection with them. As a real estate agent, my schedule is flexible a... (more)

12. Robert

Your dog may not want to go home!

Lower West Side, Chicago, IL, 60608

"Robert and his wife (and kids!) were absolutely great. My dog, Beau, is still a pup and can be a handful, but they took such great care of him. I got picture... (more)"

13. Ashlee

Dog Sitter in Spacious Condo

Near West Side, CHICAGO, IL, 60612

"Ashlee was great. Very flexible and sent us adorable pictures (more)"

Confirmed Labor Day Availability
14. Jenna

Playful Dog Lover

Bridgeport, Chicago, IL, 60608

"Jenna was great. I was in a bind and she was available to watch my collie/sheppard for 4 days at the last minute. Jenna was midnful of the fact that my dog ... (more)"

15. Corina

Dog Runner & Sitter

Loop, Chicago, IL, 60601

About: With over 8 years of volunteering at dog shelters & 3 years as a TEAM PAWS member I have developed special love for the furry guys. Your family me... (more)

16. Amanda

Fulton Market Animal Lover

Near West Side, Chicago, IL, 60661

"Amanda was wonderful with my Kaia! She was very welcoming, and flexible with my schedule. Took notes to make sure Kaia's needs were met, which made me feel m... (more)"

Confirmed Labor Day Availability
17. Kristina

a favorite aunt to you pet

Bridgeport, Chicago, IL, 60608

"Great experience! (more)"

18. Charisma

Chicago Dog lover, near dog park

Near West Side, Chicago, IL, 60607

"Charisma has been the most reliable dog-sitter I've had. For the past year, she has been watching my 4 year old German Shepard whenever I had to be out of to... (more)"

19. Ida

A home away from home

Bridgeport, Chicago, IL, 60609

"Ida was a great match for taking care of our Harlowe. She is friendly, professional, caring and great at communication. She was awesome at texting photos t... (more)"

20. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

"Bradley was awesome! He took very good care of Soni. She was sad to leave him which was a first we have seen from her outside of family. He kept us updated o... (more)"

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Dog Boarding In Chicago

The Dog Kennel Alternative

Dog owners love Rover's Chicago dog sitters. 1,724 owners have reviewed sitters in Chicago, giving them an average rating of 5/5.

Wondering how much you can expect to pay for a night on Check out our average dog sitting rates to get an idea before you start a conversation with a sitter.

Sit a Dog, Save a Life

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 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.

Animal Welfare League

The Animal Welfare League is committed to helping every pet find a good home. Their motto is "recovery is the answer, not euthanasia" for animals that come to us injured, neglected, or abused.

Everyday the Animal Welfare League saves animals lives and works to improve the way they are treated and regarded by society. In the Chicagoland area, they help all animals through their adoption programs, their low cost clinic services, their local cruelty investigations, and their public education programs. Locally they work to improve municipal, city and state laws and regulations regarding the treatment of animals and operate the state’s largest non-profit animal shelter program. They have made progress since our beginning in 1935, but much more work needs to be done.

Chicago Animal Advocates

Chicago Animal Advocates is a not for profit foster based rescue. They are 100% volunteer run. They rescue animals from high kill shelters in Illinois and Kentucky. They also take in owner relinquishments that otherwise would end up at a county shelter. All of their animals stay in the comfort of a loving foster home until they are adopted out. They believe in advocating the importance of spays and neuters and the general care of animals. Their goal is to set up fundraisers and help low income zip codes with the costs to fix their animals. Overpopulated shelters offer little time for animals to be rescued, and many do not get a second chance at life. Their number one goal is rescue and prevention.

Forever Friends Great Dane Rescue

Forever Friends Great Dane Rescue was founded by a small group of people dedicated to the Great Dane breed. Their goal is to help neglected, abandoned, and abused Great Danes find their forever homes while educating the public about the breed and responsible pet ownership. They believe that every animal deserves a forever family to love them unconditionally for the rest of their lives.

FFGDR is a foster based rescue. All of the dogs that come in to their care are placed in loving homes while awaiting adoption. They are given all medical treatment/visits that needs to be done as well as being taken in and loved as though they are part of that family. Their foster homes are able to observe the Foster Danes in a home environment with children, other dogs, other pets, and daily stresses and triggers. Their foster homes work with the Danes on any obedience or negative behaviors to start the training process for you. Their foster homes are never short on love, attention or patience to spread to the foster dogs while in their care.

Heartland Animal Shelter

Heartland Animal Shelter’s mission is to find permanent, loving homes for homeless animals and promote responsible pet ownership through education, community outreach and collaboration while maintaining respect and compassion for all creatures.

Heartland is a no-kill animal shelter and a non-profit, 501 c 3 organization. They provide food, shelter, medical treatment and loving care until homeless animals can find their forever home. Please help them save the lives of these wonderful animals by making a tax-deductible donation today.

More on Chicago

Home to the largest number of highways in the nation and second busiest airport in the world, Chicagoans are travelers as much as they are dog lovers. That's why, when preparing for a trip, Chicago dog owners want nothing but the most loving home for their dogs while they're away.

With, that gets a little easier. Scroll through our selection of loving sitters, click on a listing you like, and start a conversation. From Hyde Park to Wicker Park, sitters have access to the Windy City's only off-leash, dog-friendly areas, where dogs can play freely and recharge with special, dog-level drinking fountains and separate areas for shy pets to unwind.

You love your dog. We love your dog, too. How much? We'd love to show you. Book dog boarding, pet sitters, and dog walking in Chicago on, and stop by our blog to see what we're all about.

Useful Info on Dogs - Dog Boarding Community