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

House Sitting, Drop-In Visits, Dog Walking

8 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. Maria

I'm a professional dog whisperer :)

South Lawndale, Chicago, IL, 60623

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Maria is a phenomenal dog sitter. She specializes in presumably big dogs, always keeping her composure no matter what the situation. Dogs always feel a certa... (more)"

3. Patrick

Experienced sitter w/ huge yard

West Town, Chicago, IL, 60642

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

4 repeat clients

"I cannot think of a better dog caregiver than Patrick. Not only has he been an avid dog lover his entire life, he is also incredibly responsible, punctual an... (more)"

4. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 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)"

5. Brittany

Volunteer, Active & Professional

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Brittany was great! We needed someone to check in with our three cats to feed them and take care of the litter boxes. Our often aloof cats were well taken ca... (more)"

Confirmed Holiday Availability
6. Natalie

Loop Living and Pup Loving!

Loop, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Natalie is a lifesaver and apparently somewhat of a dog whisperer! She was early and responsible and we are lucky to have found her! (more)"

7. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

15 repeat clients

"Enoch was very friendly and personable with both me AND my cats! He was excellent with prompt communication about how much (or little) the cats were eating, ... (more)"

8. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

1 repeat client

"Britney did an excellent job with Thor. He takes a lot of patience and she had it to give. She was also very good at sending us updates regularly. I highly r... (more)"

9. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

2 repeat clients

"Adriana did a great job when watching my two dogs last week when I was out of town for work. She was reliable, followed all directions, and was very good wi... (more)"

10. Alexandria

Pup Adventures with Alex

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Alex was great! She took my reservation at the last minute for Thanksgiving weekend to take care of my cat Bean. She stopped by daily to feed Bean and play w... (more)"

11. Chelsea

Animal Trainer who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"This is the first time for us using Rover.com and I have to be honest with you, Chelsea has really set the bar high she is amazing with animals. She made su... (more)"

12. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

20 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)"

Confirmed Holiday Availability
13. Jessica

Home full time-

Near South Side, Chicago, IL, 60616

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

"Jessica is the best when it comes to reliability and dog care. She has had dogs her whole life and I have never met anyone that loves and cares for dogs and... (more)"

14. Sara

UIC area dog lover, reliable & fun

Near West Side, Chicago, IL, 60607

Drop-In Visits, Dog Walking

"Not only is Sara a super sweet person she also is great with animals. So much so that she helps me with my own dog, Zeus, all the time. And he is always so h... (more)"

Available this weekend
15. Caraline

Experienced & Certified Pet Sitter

Loop, Chicago, IL, 60606

Drop-In Visits, Dog Walking

4 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)"

16. 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)"

17. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

2 repeat clients

"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)"

Confirmed Holiday Availability
18. Simone

Professional Pet Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"From start to finish, Simone did an incredible job looking after our cats! When she came to meet them, she had already read over the information I provided a... (more)"

19. Richa

Full-Time Dog Mom!! :)

Near South Side, Chicago, IL, 60605

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

4 repeat clients

About: Hello!! I am a stay at home dog mom :). In the past year, I have been dog sitting full-time since my husband has been busy with finishing his gradu... (more)

20. Vivian

Experienced walker + home full-time

Lower West Side, Chicago, IL, 60608

Drop-In Visits

About: Hi I'm Viv! I work from home as a freelance photographer in the Pilsen area. My schedule is very flexible and I can tend to your dog at any hour... (more)

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: