Dog Boarding in Armour Square, Chicago

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

1. Richard

Retired, Devoted Doggie Dad!

Loop, Chicago, IL, 60606

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

1 repeat client

"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)"

2. 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)"

3. Marga

We can cuddle and play all day!!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

3 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)"

4. Cindy

Lots of love

Near North Side, Chicago , IL, 60611

Dog Boarding, Doggy Day Care

5 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)"

5. Sara

Puppy Fever in the Loop!

Loop, Chicago, IL, 60601

Dog Boarding, Doggy Day Care

"Sara would give excellent care to any animal. Beginning at a young age, Sara has had pet dogs. She has given loving care for each animal that was in our home... (more)"

6. Megan

Dog-deprived consultant <3

Near North Side, Chicago, IL, 60610

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

1 repeat client

"Megan LOVES dogs. I have known Megan her whole life as I am her mom and I can positively state that Megan LOVES dogs. We recently lost our beloved dog of 1... (more)"

7. Betsey

I'm bubbly, outgoing, & pup loving

Near West Side, Chicago , IL, 60606

Dog Boarding

5 repeat clients

"Betsey is awesome. Our dog has stayed with her twice and her third stay is already booked!!!! Our dog loves staying with Betsey as made her feel right at ho... (more)"

Confirmed Thanksgiving Availability
8. Magdalena

Just like home

Lower West Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care

18 repeat clients

"Madga was fantastic with Jethro. She sent me daily updates and was very easy to work with regarding drop off and pick up. I totally recommend her! Jethro cam... (more)"

9. Samantha

My friends call me a Dog Whisperer.

Near West Side, Chicago, IL, 60607

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

1 repeat client

About: Ever since I was a child, I have had a passion for dogs and animals of all sorts. Growing up in the Philippines, my relatives found it strange to h... (more)

10. Samantha

Doggy Playtime in Loving Home

McKinley Park, Chicago, IL, 60609

Dog Boarding, Doggy Day Care

5 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)"

Confirmed Thanksgiving Availability
11. Lauren

Doodle love & playtime

Near North Side, Chicago, IL, 60611

Dog Boarding, Doggy Day Care

3 repeat clients

"Beau stayed at Lauren for 5ish days and had a blast! He was soooo tired after playing with Bentley and slept like a baby for multiple days afterwards! Lauren... (more)"

12. Alyssa

Flexible, Active Dog Lovers!

West Town, Chicago, IL, 60642

Dog Boarding

11 repeat clients

"I wish I could give Alyssa more stars! You will not go wrong by having her and her husband watch your dog. From the moment we had our "meet and greet" you co... (more)"

13. Brittany

Dogs are our family

Near West Side, CHICAGO, IL, 60607

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

6 repeat clients

"Louie had a great time with Brittany and his new buddy Arro! Brittany was always quick to respond and sent lots of picture updates during Louie's stay. They ... (more)"

14. Mireya

I'm very active & love to rockclimb

Near West Side, Chicago, IL, 60607

Dog Boarding

"She did an excellent job. She gave updates whenever asked with no hesitation and was very friendly and helpful from the start. Ralph seemed to have a very go... (more)"

15. Christi

Dog Lovers in the Loop

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"I cannot rave enough about Christi and her husband! They were a fantastic duo that made sure Miley was well taken care of during her stay in their home. It c... (more)"

16. Martin

Reliable dog-experienced guy

Bridgeport, chicago, IL, 60608

Dog Boarding

"Martin watched my 2 large, rambunctious Hound dogs for about a week. He was very friendly, easy to work with, and great with the dogs! I would 110% recommend... (more)"

Confirmed Thanksgiving Availability
17. Bradley

Good times to be had.

Near West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

12 repeat clients

"I HIGHLY recommend Bradley to sit for your best buddy! He was incredibly attentive to my Bichonpoo THOR. His dogs Bolt&Apollo are very sweet and gentle. I wi... (more)"

18. Andrew

A Dog-Loving New Lawyer

Loop, Chicago, IL, 60604

Dog Boarding, Drop-In Visits, Dog Walking

4 repeat clients

"Andrew was responsive, friendly, and prompt. Our goldendoodle Bear had a great stay and came home very happy! Would definitely recommend him! (more)"

19. 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)"

20. Elesha

Boutique, individual care

Loop, Chicago , IL, 60605

Dog Boarding, Drop-In Visits, Dog Walking

17 repeat clients

"My family and I were visiting Portland and needed a day off to explore indoor areas sans our little buddy. Our dog was very happy to spend the day with Elesh... (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: