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.

1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

5 repeat clients

"Tina was wonderful with Brady! She is responsible and sweet and sent me the cutest pics of Brady! This was my first time using Rover and I'm so happy to have... (more)"

2. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Karolina stays in touch and shows that she truly cares for your pets - it helps so much when you are away! I get notes and photos constantly. I would highly ... (more)"

3. Dana

Mother of Dogs for Decades!

West Town, Chicago , IL, 60642

Drop-In Visits, Dog Walking

1 repeat client

"Dana was great! Lots of detailed updates and pics, which I love when I'm away. I definately recommend her! (more)"

4. Miki

Active dog lover!

Near West Side, Chicago, IL, 60661

House Sitting, Drop-In Visits, Dog Walking

About: I have been caring for my family dogs and have been pet sitting all my life! I currently have a 20 lb cockapoo Cooper who is very active as well. U... (more)

5. Nicole

!!PLS LET ME PLAY WITH YOUR PUP!!

Lower West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Dog Walking

"Nicole has walked and looked after my dog, Sophie, several times now and I have nothing but great things to say. She's extremely attentive, gentle and confid... (more)"

6. Brittany

Grad student dog lover

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

About: Hi I'm Brittany! I'm a Physical Therapy student and life long dog lover. I can come to you to play with your dog, care and feed, and take him/her o... (more)

Available this weekend
7. Caraline

Experienced & Certified Pet Sitter

Loop, Chicago, IL, 60606

Drop-In Visits, Dog Walking

3 repeat clients

"Caraline was great. She took great care of my kitties. She played with them and even brushed them. Now I can go on trips knowing my kitties are well take... (more)"

8. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

9. Nicole

The ultimate dog lover!

Near North Side, Chicago, IL, 60611

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

1 repeat client

"Nicole is a perfect fit for dog walking. Not only is she the most caring, considerate and loving person I know, she also adores dogs. Your dog would be in gr... (more)"

10. Ashley

Flexible schedule; long walks

Near North Side, Chicago, IL, 60654

Drop-In Visits, Dog Walking

1 repeat client

"Ashley was absolutely wonderful! She was very thorough in describing her visits with my dog & I almost felt like I was home with them. I returned home from m... (more)"

11. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

1 repeat client

"Alex took great care of my cat when I was traveling! She sent pics and kept me updated during my trip. I would recommend Alex to anyone who needs a responsib... (more)"

12. Margaret

Dog lover with vast experience!

Near West Side, Chicago, IL, 60661

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

1 repeat client

"The best (more)"

13. Lorin

Let me love your dog, like my own!

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Lorin is a great sitter/walker that truly does love puppies! She's great with dogs and actually owns two that she adores. When she met my super hyper puppy s... (more)"

14. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Our pups love Crystal and I can't imagine a better person to be part of our dog team. So grateful Crystal was able to help. (more)"

15. 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)"

16. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is always so wonderful with Scrappy and gives him tons of attention and affection. He always looks so happy in his pictures on the Rover Card. (more)"

17. Phoebe

Lots of availability - Lots of love

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Phoebe took excellent care of our Pomeranian while we spent our annual week at Disney World. It seemed like she and Moxie really bonded - we felt like we lef... (more)"

18. Braidy

Staycation for Fido

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits

5 repeat clients

About: I grew up with a dog, and haven't had the time to commit to a new little fluff ball since he had to be put down when he and I were both 17 years ol... (more)

19. Rebecca

Home full-time - Love being outside

Near South Side, Chicago, IL, 60616

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

"I have never met anyone that loves and cares for dogs as much as Rebecca does! I have had her walk/watch my dogs many times and she is so good with them. A... (more)"

20. Miranda

Needing a lovely walking companion

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I am 21 years old, I live in Chicago and have for 4 years now, and I have been raised around large and small dogs my whole life! I currently... (more)

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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: