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.

Available this weekend
1. Caroline

Caring and responsible dog lover

West Town, Chicago, IL, 60622

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

About: Hi there! My name is Caroline and I am a transplant from Philadelphia where my own family dog still lives. I started taking care of him when we got... (more)

2. Madelynn

Patient, Energic, Dog Caretaker

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Madelynn is dependable and trustworthy. She has walked dogs for me and several of my neighbors for three years and is great with pups of all sizes, ages and ... (more)"

3. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Ashleigh has been awesome and so flexible and accommodating to my last minute requests and crazy schedule. It's so great to have the same person be able to c... (more)"

4. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Grace is kind and patient with animals as she is with children. She has cared for my pets as well as several neighbors' over the years with dedication and th... (more)"

5. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Five out of Five Stars for Penelope! Our two kids/Italian Greyhounds have very different personalities. Penelope was patient and kind with our shy little gen... (more)"

6. Deepan

Compassionate care from experience.

Lower West Side, Chicago, IL, 60623

House Sitting, Drop-In Visits, Dog Walking

"Their calmness has impacted my dogs who ha e picked up on the unlimited qualities they have. My dog is usually slow to warm up to people, but with Deepan it ... (more)"

7. 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)"

8. Mia

Best Care for Your Best Friend

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

2 repeat clients

"Mia was so wonderful to work with. This was our first time using Rover and had to find someone very last minute. Mia was quick to respond and great at commun... (more)"

Available this weekend
9. Robert

All furry friends welcome!

Near North Side, Chicago , IL, 60654

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

10 repeat clients

"Robert was amazing, and at such short notice. Pudding was walked, fed and taken care of when I had to be out of town for a quick meeting at the last minute. ... (more)"

10. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"For as long as I've known her, Sidney has loved dogs, and can tell you anything and everything about them. She is kind, caring and empathic, and treats every... (more)"

11. 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)"

12. Vanessa

Fun caring dog lover.

Near North Side, Chicago, IL, 60654

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

7 repeat clients

"Vanessa was awesome. We will definitely be using her again. She and my dog got along really well and he seemed very happy when we came back from our trip. (more)"

13. 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)"

14. 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)"

15. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 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)"

16. Jing

Responsible, loving and patient!

Loop, Chicago, IL, 60601

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

About: Only take one customer's dog at a time. So your dog will be spoiled! I will send you many pictures during your dog's stay! I grow up with dogs a... (more)

17. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was great with a little doggie who is mostly afraid of people. Little Jax warmed up to her and she took great care of him. 5 Paws for Moesha (more)"

18. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Catherine has been an animal lover since I've known her. She volunteered at a dog rescue shelter while away at college and continues to volunteer with a Chic... (more)"

19. 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)

20. Ellen

Safe, Reliable and Loving Dog Care!

Near West Side, Chicago, IL, 60608

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

1 repeat client

"Ellen is a great dog walker and sitter. She has been with my dogs for six months now and knows exactly how to deal with their little nuances. I have a pup th... (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: