Pet Sitting & 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.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

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Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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1.

Crystal R.

My home is where your pet is.
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
37 reviews
12 repeat clients
from
$20
per visit

I highly recommend Crystal. She took care of my two highly active puppies for five days. It was the best feeling to know that my pups were being taking care of in the middle of the day. Crystal follows my notes exactly and always responsive.

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Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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2.

David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
47 reviews
18 repeat clients
from
$20
per visit

Highly recommend David for your pet sitting needs! He visited our two cats while we were away and did a phenomenal job. He was a great communicator and very professional.

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Sitter Profile Image: Danning X.
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Sitter Profile Image: Danning X.
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3.

Danning X.

✨WFH, caring pet sitter✨
Near South Side, Chicago, IL, 60605
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
5 reviews
1 repeat client
from
$18
per visit

Danning is a devoted pet owner! She is always reliable and caring for furry companions. She exceeds all my expectations and provides unparalleled care for pets.

Sitter Profile Image: Shimmy G.
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Sitter Profile Image: Shimmy G.
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4.

Shimmy G.

I love my pups & I’ll love yours!
Near South Side, Chicago, IL, 60605
Drop-In Visits, Dog Walking
5.0
49 reviews
13 repeat clients
from
$20
per visit

Shimmy is such an asset to the pet community - she is such a kind and loving person, and treats animals like royalty. She is raisibg two of the goodest boys and it translates so well into caring for others babies. Without hesitation, I would highly recommend Shimmy!

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Sitter Profile Image: Tucker P.
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Sitter Profile Image: Tucker P.
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5.

Tucker P.

Your dog is my dawg!
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$17
per visit

I’ve known Tucker Privette for a very long time. He is incredibly responsible, organized, and loving. Whenever my family and I have needed pet care, Tucker has always been our first choice. For as long as I’ve known Tucker, he has always been a big animal lover, and the animals always love him. My dog always gets so excited when Tucker walks through the door. You couldn’t ask for a better pet sitter.

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Sitter Profile Image: Mia M.
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Sitter Profile Image: Mia M.
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6.

Mia M.

I love all animals big and small
Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking
5.0
1 review
1 repeat client
from
$20
per visit

About: I have had the privilege of growing up with and caring for two wonderful dogs. Bella, my Great Pyrenees German Shepherd mix, has been a part of my family since 2015, in which I love taking on long walk and car rides. Additionally, I have Max, a Shih Tzu Maltese, who has been a beloved member of our family since 2011, who loves being brushed and relaxing in the sun. I truly emphasize with the challenges of juggling a hectic schedule while ensuring that our furry companions receive the utmost care and attention they deserve As a college student in Chicago, I have available time after classes during the week and on weekends, making it easy to incorporate pet care into my weekly routine I’m exceptionally attentive to pet care. For walks, I maintain keen awareness of my surroundings. When checking in on dogs, I ensure they have ample food and water at the beginning and end of each visit whilst following and analyzing care instructions to be carried out. Furthermore, I’m more than willing to engage with energetic puppies and dogs to help them expend their energy through play and walks. Your pets’ well-being and happiness are my top priorities.

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Sitter Profile Image: Luis G.
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Sitter Profile Image: Luis G.
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7.

Luis G.

Here to make DOGS feel like DAWGS!
Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$20
per visit

Luis has a great love for animals! He is exceptionally knowledgeable about proper care and training for dogs as well as cats. His work raising his own dog shows his dedication and nurturing nature that a pet needs to be happy.

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Sitter Profile Image: Josie S.
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Sitter Profile Image: Josie S.
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8.

Josie S.

Animal Whispering Weirdo
Chicago, IL, 60608
Drop-In Visits
5.0
4 reviews
from
$20
per visit

Josie was a great sitter and very knowledgeable about cat care. She is considerate, communicative, and punctual; exactly what we want in a pet sitter.

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Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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9.

Coretta S.

Loves to accommodate furry friends
South Shore, Chicago, IL, 60649
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
10 reviews
7 repeat clients
from
$17
per visit

Coretta was an amazing caretaker. She was consistent, on time, gave me thorough updates, and provided great care for my pets. 15 out of 10 would recommend!

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Sitter Profile Image: Max C.
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Sitter Profile Image: Max C.
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10.

Max C.

Pawsitive Trainer & Walker
Chicago, IL, 60608
Drop-In Visits, Dog Walking
5.0
28 reviews
15 repeat clients
from
$26
per visit

Max was very friendly and very aware of my dogs wants and needs. I will continue to use max for our future dog watching services.

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Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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11.

Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
159 reviews
70 repeat clients
from
$24
per visit

Dalila was great with my cat Shelby! She went out of her way to make my cat (who is afraid of strangers) feel at ease, and she even warmed up to her sooner than I expected. I’d definitely hire her again!

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Sitter Profile Image: Emily O.
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Sitter Profile Image: Emily O.
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12.

Emily O.

Emily O- pet lover forever!
Loop, Chicago, IL, 60605
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
18 reviews
3 repeat clients
from
$26
per visit

Emily helped by coming by each day to clean my kitties litter boxes while I was away and she did a phenomenal job! Super communicative and very clearly an animal lover that prioritizes our pets like her own while she cares for them!

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Sitter Profile Image: Taiyo N.
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Sitter Profile Image: Taiyo N.
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13.

Taiyo N.

Ready to Care for Your Beloved Pet!
Near West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
from
$22
per visit

Taiyo is a very polite, punctual and helpful young man. He looked after our dog very well and I would highly recommend him!

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Sitter Profile Image: Chi O.
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Sitter Profile Image: Chi O.
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14.

Chi O.

Fun Loving Dog Enthusiast
Grand Boulevard, Chicago, IL, 60653
Drop-In Visits
6 years of experience
from
$18
per visit

About: I love dogs! I always have, and have my own puppy best friend at home with me. I’m so excited to love on your furry friends just as much as I do mine. I love long walks with lots of pauses for sniffing and exploring, and plenty of indoor playtime with my dog Mini. I’m also big on healthy treats and snacks. Aside from my dog, I’ve also had plenty of fun dog-sitting for other dogs of small to medium size. Choose me to give your pup an exciting, dynamic vacation while you’re gone! I’m currently a student at Booth which means that most of my time is free (class on average only 3 hours a day) and I’m close by to check on pups! I am big on walks, pets, and enrichment interactions to keep pups mind as occupied as their body. That being said, I know you know best and I’ll follow your instructions on treats and playtime to disrupt your dogs routine as little as possible.

Sitter Profile Image: Logan T.
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Sitter Profile Image: Logan T.
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15.

Logan T.

Its a dog thing and we understand
Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$20
per visit

I'm usually pretty nervous about leaving my dog with new caretakers while I'm away on trips or stuck in office but I lucked out finding someone as reliable and awesome as Logan! My 5 year old pup absolutely adores him and the attention/care he receives when Logan comes to visit. I love the communication and consistent updates that I get from Logan when he's overnight sitting for me or just taking my fur child for walks around the neighborhood. You can tell how much he loves dogs by how patient he is with not only the doggos but their anxious parents as well. It's a relief to know I can leave my fur child with someone I can trust when I have to be away. I honestly don't know what I would do without him!

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Sitter Profile Image: Hunter S.
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Sitter Profile Image: Hunter S.
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16.

Hunter S.

Attentive & Friendly Pet Care🐾
Lower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking
5.0
23 reviews
3 repeat clients
from
$25
per visit

Hunter is one of the most considerate dog walkers I’ve used yet and I am unbelievably grateful for his help each week. My dog and my home have been wonderfully cared for by this individual and I recommend him highly.

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Sitter Profile Image: Kathryn F.
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Sitter Profile Image: Kathryn F.
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17.

Kathryn F.

A fun, reliable human for every 🐶
Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
1 repeat client
from
$15
per visit

Kathryn was excellent in her care of Finn. She was a great communicator, giving me detailed reports of her check ins and how he was doing. He’s got a lot of quirks and I felt confident in her abilities to handle them. Definitely recommend her service. Will be booking her again for future travel.

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Sitter Profile Image: Lucy S.
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Sitter Profile Image: Lucy S.
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18.

Lucy S.

Rover 101
24/7 loving pet sitter WFH
Chicago, IL, 60601
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
10 reviews
from
$35
per visit

Lucy is a great sitter. She is responsible and took good care of my cats. She sent me pictures and messages during visits just to make sure my cats got what they need. I’d definitely recommend her and use her service again if needed!

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Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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19.

Otis B.

Dog's Best Friend
Near West Side, Chicago, IL, 60612
House Sitting, Drop-In Visits, Dog Walking
5.0
35 reviews
17 repeat clients
from
$25
per visit

Otis was able to take a last minute request which helped me in a huge way from me cancelling an important trip. He took care of my pets incredibly well during his visits and offered to house sit as well for no additional! He was communicative everyday and sent me great status reports. Would recommend Otis 5/5!

Sitter Profile Image: Erik W.
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Sitter Profile Image: Erik W.
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20.

Erik W.

Flexible schedule for cats and dogs
Chicago, IL, 60608
Drop-In Visits
5.0
14 reviews
1 repeat client
from
$17
per visit

Erik was great! He took care of Ghost like she was one of his own. Tons of photos and updates which is great. Ghost doesn’t like being alone for too long so it was perfect having Erik to check in on her and make sure she gets some love each day.

Search Map

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:

Drop-In Visits