House Sitting in Douglas, Chicago

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Search Results

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Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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1.

Jasmine P.

Rover 101
Beloved dog whisperer, is me!
Chicago, IL, 60604
House Sitting, Drop-In Visits, Dog Walking
5.0
35 reviews
12 repeat clients
from
$75
per night

Jasmine is an amazing sitter and did a great job taking care of our dog over a five-day period. She gave us plenty of tips for handling/training our reactive puppy, provided lots of updates, and made us feel very at-ease having a sitter take care of our dog, who can sometimes be scared/anxious around strangers. She also took great care of our apartment and everything was neat and tidy when we came back. Highly recommended!

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Sitter Profile Image: Annie B.
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Sitter Profile Image: Annie B.
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2.

Annie B.

Large or Small - I Love 'em All!
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
42 reviews
20 repeat clients
from
$100
per night

Our kitty was so well taken care of by Annie! We were able to fully enjoy our short trip knowing that she was keeping our cat fed and happy. Annie’s photos of our kitty were adorable!

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Sitter Profile Image: Alysia G.
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Sitter Profile Image: Alysia G.
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3.

Alysia G.

Reliable, non-smoking pet lover
Chicago, IL, 60616
House Sitting, Dog Walking
5.0
11 reviews
7 repeat clients
from
$60
per night

Always a pleasure to have Alysia pet sit/house sit for us.

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Sitter Profile Image: Pablo V.
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Sitter Profile Image: Pablo V.
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4.

Pablo V.

Rover 101
Fun walks
Near West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking
5.0
211 reviews
90 repeat clients
from
$59
per night

We left our pup with Pablo for another long weekend and once again we are so happy with Pablo. Ajax just adores him and our house is kept in such great condition when he’s out. We get plenty of updates with pictures throughout the day and Ajax is plenty tired when we see him! We’ll definitely be calling Pablo on our next trip.

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Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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5.

Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
152 reviews
68 repeat clients
from
$60
per night

Dalila took such great care of my fur baby. This was my first time having someone watch my dog while housesitting! She sent me pictures daily, updated me constantly and left the house super clean and my dog super happy ? I will def rebook again!!

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Sitter Profile Image: Molly S.
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Sitter Profile Image: Molly S.
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6.

Molly S.

Openly Available Animal Caretaker
Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
2 repeat clients
from
$45
per night

Molly was wonderful with my pup Otto and I came home to a very happy dog. Molly was also great with watching my home while sitting for Otto. Highly recommend!

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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7.

Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
80 reviews
24 repeat clients
from
$50
per night

This was our first time having Emily watch our fur babies and we couldn't be happier! She was fantastic!! Just came home to find 3 very happy pups and she also left the house and plants in amazing shape. We were gone for 10 days and received lots of great updates and pictures. We felt super comfortable leaving the pack in her care and will definitely request her again in the future. Thanks so much Emily!!

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Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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8.

Crystal R.

My home is where your pet is.
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
37 reviews
11 repeat clients
from
$65
per night

Crystal is the most thoughtful and caring dogsitter we’ve had! Arthur immediately connected with her and she sent us updates and pictures while we were away. She also took such great care of our home! I would highly recommend Crystal as she is very responsible, kind and trust worthy!

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Sitter Profile Image: Candice B.
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Sitter Profile Image: Candice B.
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9.

Candice B.

Just waiting to play fetch!
Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
39 reviews
14 repeat clients
from
$80
per night

Candice was great watching my 2 spunky pups! She sent great pics and updates and even taught them a new trick. They are active and she took them on longer walks to some of their favorite places. She was great and will definitely book her again!

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Sitter Profile Image: Janette V.
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Sitter Profile Image: Janette V.
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10.

Janette V.

People call me Snow White lol
Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
3 repeat clients
from
$75
per night

Janette is awesome! She spoiled my senior girl Lana during a quick outing I had planned. Janette took her for a pup-accino and back to her house so she could sunbathe and people watch. And Janette always provided updates. Lana was happily exhausted when I got home that day!

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Sitter Profile Image: Leah R.
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Sitter Profile Image: Leah R.
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11.

Leah R.

Playing with puppies is my passion!
Near North Side, chicago, IL, 60611
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
6 reviews
from
$45
per night

Leah is amazing I think my dog likes her more than he likes me now!

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Sitter Profile Image: Riss B.
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Sitter Profile Image: Riss B.
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12.

Riss B.

Attentive and enthusiastic care
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
55 reviews
17 repeat clients
from
$50
per night

Riss was extremely caring, communicative, and a terrific sitter for our cats. We felt extremely comfortable leaving our cats for multiple days, and consistently received updates and photos. Riss was flexible and was great about working with our cats routine and over-excitement around feeding time. They had a great time, and would definitely have Riss sit for us again.

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Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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13.

Allison J.

Previous Veterinary Technician
Near West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking
5.0
40 reviews
20 repeat clients
from
$80
per night

Allison was great! She was very accommodating and communicative before the stay, and continued to be awesome throughout the stay. She sent pictures and updates throughout the weekend, which I really appreciated. We came home to a super happy pup and a very clean home! I will definitely be using Allison again and can’t recommend her enough! Thank you so much Allison!!

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Sitter Profile Image: Lindsay J.
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Sitter Profile Image: Lindsay J.
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14.

Lindsay J.

Cat mom and animal lover
Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking
5.0
19 reviews
6 repeat clients
from
$65
per night

Lindsay is great! I travel regularly for work and she is always willing and able to accommodate the early departures and late arrival. She’s very respectful of my place and sends constant updates. My dog loves her and I book her regularly.

Sitter Profile Image: Ye S.
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Sitter Profile Image: Ye S.
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15.

Ye S.

Cats are family!
Bridgeport, Chicago, IL, 60608
Boarding, House Sitting
1 review
1 repeat client
from
$250
per night

Hi, It’s Evelyn here! It’s my pleasure to have an opportunity to recommend Ye to everyone who loves cat! He is super considerate and I have never seen a cat that does not like him, if only you could hear the purring of my cat on his lap, that’s how lovely he is in the cat’s eyes!

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Sitter Profile Image: Munder S.
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Sitter Profile Image: Munder S.
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16.

Munder S.

Your pet needs some me time too
West Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking
5.0
86 reviews
34 repeat clients
from
$60
per night

Munder is great! We’ve booked him several times for our German shepherd puppy who is definitely a handful! Our house is always how we left it and he watches her closely so nothing in our house gets damaged. He does an amazing job with her!

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Sitter Profile Image: Quinn H.
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Sitter Profile Image: Quinn H.
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17.

Quinn H.

Graduate Student missing my animals
Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
1 repeat client
from
$50
per night

Quinn was absolutely great! Prompt, responsive, and responsible! Jackson was well taken care of under her watch, which is no easy task. He’s a 115 pound sass pup but she managed him flawlessly! Followed the care instructions to a T and I came home to a cleaner has then I left! I definitely recommend and will be using her again in the future! Thanks again for your help this weekend!

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Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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18.

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
$55
per night

This was our second time booking Otis, the first time was from my partner’s account. Otis is reliable, responsive, and always keeps us up to date with pictures. We hired him again for a long day of house sitting because I had a long day at the office. He arrived bright and early at 7:30 and stayed until 6pm! When I had warned him that Reese was in heat, he was very kind and accepting that it was just nature. That helped reassure me that this wasn’t going to be an even more stressful situation. Otis is extremely reliable and cares deeply for the pups. He’s been able to handle our puppy and dog at the same time. Happy to continuously book him. He’s a great rover.

Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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19.

Belicia K.

Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
12 reviews
6 repeat clients
from
$50
per night

My cat sitter cancelled on me at the last minute. But as it turns out I was meant to find Belicia. She took excellent care of my girl Zuri. Belicia was communicative, kind, and followed all instructions. She sent me messages and photos to absolve any worry and it didn't take long for my anti-social kitty to take to her. Having her care for Zuri was such a peace of mind. When I came back home, I realize that everything worked out as it should have. This is the beginning, as I will be scheduling with Belicia again.

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Sitter Profile Image: Sharett B.
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Sitter Profile Image: Sharett B.
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20.

Sharett B.

Your dog's new best friend.
Chicago, IL, 60605
House Sitting
5.0
59 reviews
24 repeat clients
from
$70
per night

Sharett took great care of Atticus, provided updates, and was good with giving him his medication. She left my home exactly how it appeared when she arrived :). Would definitely recommend her for dog sitting in your home!

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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.

House Sitting