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. Rebecca

Your dogs new pal and confidant

Lower West Side, Chicago, IL, 60608

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

"Rebecca is amazing with dogs, especially my nervous Jack Russell. She was able to instantly make friends with him and he loved to be around her. The pinnacle... (more)"

2. Krista

Flexible schedule, love dogs

Hyde Park, Chicago, IL, 60615

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

About: Other dog owners describe me as a caring, responsible, loving dog lover and pet sitter. I'm a current grad student so I have a flexible schedule to... (more)

3. Maria

Biggest cat and dog mom ever

South Lawndale, Chicago, IL, 60623

Drop-In Visits, Dog Walking

About: My experience with dogs include 3.5 years of volunteering with court case dogs with Safe Humane Chicago. It included interacting with dogs, facilit... (more)

4. Cosette

Forever dog-lover

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi there! I am a careful and attentive dog (and kid) sitter, with lots of love to give! I have owned and cared for dogs since a child and currently... (more)

5. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Karolina has sat and done walks for me 3 times. She is very responsive and sends followup messages to let me know how things are going. Will definitely wor... (more)"

6. Isabella

Summers off and energetic

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Isabella is the true definition of an animal lover. She truly appreciates animals, unlike anyone I have ever met. Whenever she sees a dog, she rushes over to... (more)"

7. Payal

West Town Pet Sitter

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Payal was a better dog-sitter than I could have hoped for. It was our first time leaving Zeke alone with a stranger and she was very caring and attentiveness... (more)"

8. Allison

Beloved pet care for your dog!

Near West Side, Chicago, IL, 60661

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

"Allison is a caring, dependable, compassionate professional whom I have known for 7 years. In the time I have gotten to know her, she has proven herself to b... (more)"

9. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

"Adriana is very efficient, caring and will take care of your pet as her own! Her flexibility and attention to detail is what makes her stand out, not to ment... (more)"

Available this weekend
10. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Hello, Rover! Simone has cared for my pup, Honey on several occasions & I have never come home to an unhappy pet! She is kind and where Honey is concerned... (more)"

11. KC

Loving Pet Sitter/Nursing Student

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"KC was great and sent pictures each day. I really appreciated her amazing communication before, during, and after the pet sitting! (more)"

12. Katy

Knowledgable & reliable caregiver!

Near North Side, Chicago, IL, 60654

Drop-In Visits, Dog Walking

2 repeat clients

"Katy is wonderful! She checked in on my cat while I was out of town for several days and I can tell they had a lot of fun together. Katy was very professiona... (more)"

13. 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)"

14. 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)

15. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

16. Madison

Pup Loving Student

Loop, Mount Pleasant, SC, 29466

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Madison was great! Very communicative and sent me photo updates of my cat each day which I appreciated immensely. I would use her services again! (more)"

17. Christian

PAWS volunteer,rescuer

McKinley Park, Chicago, IL, 60609

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

1 repeat client

"Christian was awesome and extremely accommodating with such short notice! He came to a meet and greet literally the night before we needed him. He was friend... (more)"

Available this weekend
18. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Netiya was amazing!!! We had to book a cat sitter last minute and Netiya was both very responsive and flexible! She sent us photos of our cat while we were a... (more)"

19. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

17 repeat clients

"Penelope is fantastic!! She took excellent care of our pets. Her communication was great and no reasonable request was denied. We strongly recommend her serv... (more)"

20. 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)"

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: