Pet Setting & Drop Ins in Armour Square, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Mark

Bark Voyage!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits

About: Being away from you is stressful for your dog, so why make it even more stressful by making your furry friend leave home? I am a 26 year old Chic... (more)

2. 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)

3. Abby

Experienced Sitter Loves All Pets!

Douglas, Chicago, IL, 60616

Drop-In Visits, Dog Walking

11 repeat clients

"Absolutely excellent! She was available same-day within the hour -- she is awesome. Highly recommended! (more)"

4. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"To whom it may concern, Hailey is a very positive and optimistic person. She is caring and very thoughtful and the positive energy she brings makes her a ... (more)"

Confirmed New Years Availability
5. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Perfect pet-sitter! We highly recommend her. (more)"

Confirmed Holiday Availability
6. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

Available this weekend
7. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emma was incredibly accommodating; offered to come over for a meet and greet so I could show her around, and we could chat through the stay. She worked with ... (more)"

8. Stefani

Dog lover-looking to love your pet

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Stefani is awesome and did a great job! (more)"

9. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

5 repeat clients

"Tina did a great job taking care of our two cats while we were out of town for a long weekend! She was very responsive to our requests and was readily availa... (more)"

10. Bernadine

Professional & Caring Dog Sitter

Near North Side, Chicago , IL, 60611

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

About: Hello! My name is Bernadine and I love dogs!! I have always loved animals and grew up with both cats and dogs. I have over 15 years of caring for a... (more)

11. Sam

Improving lives, one dog at a time

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"She's amazing. She had no trouble with my kitten. He isn't used to people but he had no trouble warming up to Sam. She even brought packages inside and manag... (more)"

Confirmed Holiday Availability
12. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Netiya watched my cat, Harvey, while I was away on an extended weekend. She updated me with photos and messages! Would definitely use Netiya and her services... (more)"

13. Kellin

Responsible, caring, lover of dogs!

Near North Side, Chicago, IL, 60654

House Sitting, Drop-In Visits, Dog Walking

"Kellin did a great job taking care of our pup for the night and sent us picture updates on his walk. Thanks again! (more)"

14. Rory

I love and appreciate all pups

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was great! She was able to stop in at 3am on two nights. (more)"

15. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

" Emily has been in the dog-caretaking business for four years. There is nobody I'd recommend before her. Not only is she extremely trustworthy on all levels... (more)"

Confirmed Holiday Availability
16. Alexis

Law Student and Dog Lover

Loop, Chicago, IL, 60605

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

2 repeat clients

"Alexis was great and she always kept us updated! (more)"

17. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sabrina is a very loving, caring, responsible dog caregiver. She took care of our Doberman Max from puppy-hood until his last day on Earth. She also took c... (more)"

Confirmed Holiday Availability
18. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

About: I moved to Chicago from Gainesville, FL to get a fresh perspective and a change of pace. I'm an artist who spends most of my time making comics and... (more)

19. Maddie

I absolutely love all animals!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Maddie was great! She sent me Rover cards with pictures of Coco. When we returned home Coco was very happy! We definitely recommend Maddie and we'll be using... (more)"

20. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Hello! My name is silvia. I was an animal caregiver at PAWS Chicago for 2 years. PAWS is a nationally known no-kill shelter with a hospital located... (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 in Armour Square, Chicago, IL love dog sitters on Rover.com. 7,915 owners have reviewed sitters in Chicago, giving them an average rating of 4.9/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Armour Square pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Armour Square, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Armour Square pet sitters and avoid the kennel.

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 Armour Square, 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: