House Sitting in Armour Square, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

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Pablo V.
1.
Fun walksNear West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Pablo was absolutely amazing! Our dogs are a bit aggressive outside with other dogs and we felt at ease knowing that Pablo could handle whatever they would enco… (more)

from
$48
per night
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Crystal H.
Loves all animalsBridgeport, chicago, IL, 60609
House Sitting, Drop-In Visits

Crystal is the best pet momma I can imagine! Our very finicky dog jumped into her lap on her first visit with him. You know that dogs know a good person and I h… (more)

from
$45
per night
Anthony H.
Pilsen Dog Walker/Cat Sitter!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting

Anthony was so sweet, communicative and caring while watching our senior pup. He sent many pictures and videos which really helped to put us at ease while being… (more)

from
$40
per night
Maeve P.
4.
Flexible schedule, big fenced yard!Hyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Mauve was so sweet and accommodating. Not only was she timely and responsive, she was also flexible when I told her I would be late coming home. My dog seemed… (more)

from
$55
per night
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Emma B.
5.
Amazing Animal CaregiverLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Emma is a very close friend of mine and she is a great pet owner! She has watched my dog and cats before and I’ve always been more than satisfied with her servi… (more)

from
$50
per night
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6.
Trustworthy, respectful, and fun!Near South Side, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Nikki was a great sitter for my pup. She was very communicative throughout, sent photos of her with my dog playing in the park, and left the house in better sha… (more)

from
$40
per night
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7.
Home Full Time-Big Fenced in SpaceBridgeport, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Randi is an expert in pet care. She puts so much love into the animals she works with. I would trust her with my pets anytime. On top of that, she makes the mos… (more)

from
$70
per night
Passionate Pet Care ProviderLoop, Chicago, IL, 60604
House Sitting, Drop-In Visits, Dog Walking

He did a great job taking care of our 2 dogs again. I think it’s the third time he’s stayed at the house to watch them. He does a great job of communicating and… (more)

from
$50
per night
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9.
Certified Dog Lover🤍 🐶 🐕Loop, Chicago, IL, 60601
Dog Boarding, House Sitting, Dog Walking

Maddie was great! Our pup has had trouble crate training and we needed someone to be at our house for a while while we were gone. Maddie was professional and we… (more)

from
$40
per night
Happy pup happy life!Douglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Wow Brittany was amazing!! I was gone all day because of work, she was very communicative and kept me updated on how my dogs were doing. Definitely recommend!! (more)

from
$30
per night
11.
There’s no place like home!❤️❤️❤️Lower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Erica was fantastic with Faith! She houses sat for me and took care of my cat like it was her own. Faith was happy when I got back, it is the best I have seen h… (more)

from
$30
per night
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12.
Flexible schedule, adore dogs!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

There are only a handful of people out there that I wholeheartedly trust with my pup - and Angie is one of them. She and I trade off with another friend of our… (more)

from
$40
per night
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A house is not a home without a dogNear West Side, Chicago, IL, 60661
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi, My name is Mark I've lived with dogs and cats most of my life my. I'm 19 and like pets and being around them. My family is a dog family. . Me an… (more)

from
$35
per night
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Our sweet dog loves friends!Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Caroline has a small dog of her own that she takes wonderful care of! I have also left my own boston terrier with Caroline on many occasions, and she has taken … (more)

from
$50
per night
15.
I treat your pet like my ownNear West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

Mike was amazing. I am hoping my dogs were well behaved enough he'll want to stay again, ha! He sent updates and pictures throughout the stay. He checked in wit… (more)

from
$60
per night
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16.
Trustworthy Dog Care!Loop, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

She did a great job taking care of all 3 of our dogs. Very reliable on timing and caring for our dogs. I would highly recommend! (more)

from
$50
per night
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17.
Great with Dogs!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Tylor is the best! He is super communicative and takes the BEST pictures. I always feel comfortable going away when i know hes watching my pup! (more)

from
$40
per night
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Care your baby like my ownNear South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Chanakarn was great! Super responsive and left me with no concerns while she was watching my pets. I came back to them happy and content. I’d definitely use he… (more)

from
$50
per night
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19.
Your friendly & helpful neighborLoop, Chicago, IL, 60607
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Hi, my name is Anna. I’m so glad you came across my profile. 🙂 I’m a marketing professional who’s working from home fully remote. I have been sur… (more)

from
$39
per night
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20.
I love playing & caring for animalsBridgeport, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hey, I’m Rachel and I’ve owned pets my whole life. I have one dog of my own at my family home and a cat that I’ve had almost my entire life (16 and s… (more)

from
$30
per night

Rover also offers House Sitting in:


The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving 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 house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. 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 house sitters for your pets--and avoid the kennel.

Want to learn more? Check out reviews from pet owners who have used Rover.