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.

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1. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jennifer was great to communicate with! We will be asking her to drop-in in the future. (more)"

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2. Presley

lifelong pet owner; home full-time

Near South Side, Chicago, IL, 60605

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

"Presley took amazing care of Latika and kept us updated with videos and pictures, she had a great fit with Latika and we will look for Presley for future pet... (more)"

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3. Sanford

Accepting new dog and cat clients!

Near South Side, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Commmunicative and super helpful. Went above and beyond.Will be using his services again. (more)"

Confirmed availability
Christmas and New Year
4. Esther

South Loop, Full-Time Fun

Near South Side, Chicago, IL, 60616

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

About: Welcome, Rover friends. Consider leaving your friendly pup with me. I'm active and love the outdoors. Our home is clutter and stress-free. Calm wal... (more)

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5. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Ivana is amazing with my two cats! I completely trust her taking care of them when I am away. She always sends pictures of Duffy playing and manages to find ... (more)"

6. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"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)"

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7. Chelsea

Available all day all summer!

Lower West Side, Pilsen, IL, 60608

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

"Chelsea is the biggest dog lover I know. Since she doesn’t have a dog or her own, this job will give her the amazing opportunity to walk and take care of all... (more)"

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8. Jonathan

I watch your pets so you can relax!

Loop, Chicago, IL, 60602

House Sitting, Drop-In Visits, Dog Walking

"We had a last minute crisis when some friends could no longer check in on our two kittens and Jonathan saved the day! We contacted him the night before we ne... (more)"

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9. Angelica

Home full-time, flexible schedule.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Angelica is my go to person for anything dog related. She’s knowledgeable about what a dog may need/want and has had ample experience looking after and carin... (more)"

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10. Zak

Home all day - fenced yard

Douglas, Chicago, IL, 60616

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

About: I am a very active person, can handle any dog. I have experience with big and small breeds of dogs. Taken positive reinforcement dog training class... (more)

Confirmed availability
Christmas and New Year
11. Chenika

Fun & Passionate Sitter!

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits

"Chenika was very accommodating with a last minute booking. I returned home to very happy well-fed cats, and clean litter boxes. Many thanks and I would highl... (more)"

12. Katlyn

Consistent & Loving :)

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Excellent sitter for my two cats!! (more)"

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13. Natalie

Long time owner first time walker

Loop, Chicago, IL, 60605

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

"Natalie is a reliable, dog-loving person who would make sure to take the best care of your best friend! She has had experience with dogs her whole life and i... (more)"

Confirmed availability
Christmas and New Year
14. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

"Enoch went above and beyond our expectations for watching our cats. Not only did Enoch take really good care of them and keep us updated about their well bei... (more)"

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15. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel is wonderful with my dog! I have a 70 pound pit mix that likes to pull and, while she looks tiny, she manages to control and hold onto Kobe quite easil... (more)"

16. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Tina is *excellent.* She was wonderful with my 2 large dogs during my first weekend away from home. Her care is extremely reliable, conscientious, and kind.... (more)"

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17. Sharon

Home all day! large dog park!

Near South Side, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Doggy Day Care

"Sharon is our first choice when it comes to caring for our dog Jack. She is always reliable, trustworthy and professional. We have used her Sevices on severa... (more)"

Confirmed availability
This weekend
18. Fabienne

:) Snuggled Up, Happy & Healthy !

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"My cat and I were very happy with Fabienne! She sent many updates and photos, and let me know if she was going to be late. She was so patient with Vic and sp... (more)"

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19. Katie

Long walks and warm cuddles

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"My experience with Katie was great. My partner and I were traveling out of town for a funeral the following day when I contacted Katie to watch our Yorkshire... (more)"

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20. Megan

Last minute bookings available!

Armour Square, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Megan was fantastic. She was reliable and responsive to our questions. She sent great updates with photos and the kitten's seemed to love her. We would highl... (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: