Dog Boarding in West Englewood, Chicago

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

1. Megan

Super South Loop Sitters

Near South Side, Chicago, IL, 60605

Dog Boarding

"My dog Rizzo is my child and I wouldn't trust her with anyone else besides Megan. As an avid dog mom herself, Megan doesn't just puppy-sit, she extends her h... (more)"

2. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

3 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)"

3. Liz

Tails are wagging here!

Beverly, Chicago, IL, 60655

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

8 repeat clients

"Liz was AWESOME with being so accommodating for my dog Daisy when I had a conference to go to. She has a little dog, and the two dogs had a blast together. S... (more)"

4. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

5 repeat clients

"Great stay for Tio. He had plenty of walks and fun with doggie day care visitors. Nice location near a park. Back yard available for scratching his back wi... (more)"

5. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 repeat clients

"Magdalena was extremely responsive throughout my dog's stay. I truly appreciate how attentive she was to my pup, and how understanding she was for often I li... (more)"

Confirmed Thanksgiving Availability
6. Samantha

Weekend doggy oasis

Gage Park, Chicago , IL, 60632

Dog Boarding, House Sitting

"Samantha was great! She's very patient. I've been trying to find Chloe a dog sitter who can deal with her personality for a long time and I've finally found ... (more)"

7. Abi

Our home is your dog's home!

Kenwood, Chicago, IL, 60615

Dog Boarding, Doggy Day Care, Dog Walking

About: My husband and I love dogs! We've both grown up babysitting and loving dogs but never having one of our own. We think they're great pals for advent... (more)

8. Noreen

Loving and fun dog sitter!!

Beverly, Chicago, IL, 60643

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

12 repeat clients

"Greta was very well cared for by all host family members. Noreen worked with Greta to make her feel more comfortable in strange surroundings. Greta was wip... (more)"

9. Keeshina


Grand Crossing, Chicago, IL, 60619

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

About: Hi , My name is Keeshina As a kid Me & my sisters Loves any pet we come in contact with!! My sis has 2 pits 2 cats other a Lil tea cup! I ha... (more)

10. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

"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)"

Confirmed Thanksgiving Availability
11. Tanisha

Taking care of your best friend!

Ashburn, CHICAGO, IL, 60652

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

1 repeat client

"I am very pleased to say that our Zeus's stay with Tanisha was grea! Tanisha sent picture updates on a regular basis as well as provided videos of our pup du... (more)"

12. Manpriya

Lots of Love to go around

Ashburn, Chicago, IL, 60629

Dog Boarding

2 repeat clients

"Super flexible, easy to work with and great communicator. Would definitely recommend and rebook in the future! Thanks for everything Manpriya! (more)"

13. Dawn

Choose Dawn! I'm not JUST a soap..

Grand Boulevard, Chicago, IL, 60653

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

2 repeat clients

About: I believe about half of my heart is filled with my love for dogs, the other have is Johnny Depp and Mac and cheese! I've taken care of about 20 dog... (more)

14. Megan

Dogs are family!

Gage Park, Chicago , IL, 60632

Dog Boarding, Doggy Day Care

1 repeat client

"Megan was great! I felt very comfortable leaving my baby with her and when I picked him up he seemed relaxed and happy. I would definitely recommend her to a... (more)"

15. Gail

Work from home sitter available!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

About: In our house, pets are a part of the family. People with busy schedules should still be able to enjoy the love and companionship of a dog. I have... (more)

Confirmed Thanksgiving Availability
16. Renee


Ashburn, Chicago, IL, 60652

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

4 repeat clients

"We left Onyx for week in Renee's care. She was thoughtful enough to send pictures and updates of our baby's progress. They treated our puppy like one of t... (more)"

17. Hilda

Family environment - Just like Home

Brighton Park, Chicago, IL, 60632

Dog Boarding, Doggy Day Care, Dog Walking

4 repeat clients

"My dog Deacon had a great time with Hilda this past weekend. He is a larger dog, but enough used to apartment living that I knew a small space would work for... (more)"

18. Randi

Loved animals all my life.

West Englewood, Chicago, IL, 60636

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

About: Hi everyone my name is Randi I am a 22 year old college student and I enjoy animals especially dogs and cats. I think its because they show you how... (more)


Little Paws Home

Chicago Lawn, CHICAGO, IL, 60629

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

2 repeat clients

"It was my first time leaving my sweet Toby and using Rover and I would highly recommend and trust Armando to watch over my my Silly Toby anytime. I left Toby... (more)"

20. Maritere

My spirit animal is a mama dog!

Gage Park, Chicago, IL, 60632

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

About: I am a diligent, caring, and loving dog sitter. Dogs have always loved to be around me and I around them. I love to take care of cute pets and dogs... (more)

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Learn About Premier

Dog owners love Rover's Chicago dog sitters. 9,532 owners have reviewed sitters in the Chicago metro area, giving them an average rating of 5/5. Browse profiles, read reviews, and check us out on Yelp.

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.

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.

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 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 nonprofits across the U.S., including: