House Sitting in Loop, 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
Which dates do you need?
What size are your dogs (lbs)?

Search Results

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Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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1.

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

After a seven night stay, we couldn’t be happier! The dogs seemed happy, we got photos / communication every day, and the house was even left clean. We would use again / recommend to anyone!

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Sitter Profile Image: Munder S.
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Sitter Profile Image: Munder S.
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2.

Munder S.

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

Munder is so very sweet with our Paxton! He played ball with him routinely and kept me up to date on how things were going. He was very respectful of our home and I’ll happily have him care for Paxton again!

Sitter Profile Image: Ann Marie M.
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Sitter Profile Image: Ann Marie M.
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3.

Ann Marie M.

In a bind? I’d love to help!
West Town, Chicago, IL, 60482
House Sitting, Drop-In Visits, Dog Walking
5.0
65 reviews
25 repeat clients
from
$85
per night

Ann Marie was such a gift to watch our dog Leo! Leo has separation anxiety & general nervousness. Ann Marie was so gentle, patient, and understanding. While watching Leo for one night she sent no less than 10+ pictures/videos, updates, took him on numerous walks, and to the dog park! He was spoiled for sure. Thank you for caring for Leo like he was your own!

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Sitter Profile Image: Lindsay J.
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Sitter Profile Image: Lindsay J.
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4.

Lindsay J.

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

Lindsay was so nice and eased our worries with using a dog sitter for the first time. She kept us updated on how our dog was doing multiple times a day and followed our instructions to a T! Thanks Lindsay!

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Sitter Profile Image: Hunter S.
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Sitter Profile Image: Hunter S.
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5.

Hunter S.

Attentive & Friendly Pet Care🐾
Lower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking
5.0
23 reviews
4 repeat clients
from
$50
per night

So grateful to have found Hunter. He was fantastic with my dog and did everything, feeding, walking, and cuddles. Definitely will be asking Hunter For help again!

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Sitter Profile Image: Madison L.
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Sitter Profile Image: Madison L.
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6.

Madison L.

Animal-Loving Med Student
Near North Side, Chicago, IL, 60611
House Sitting, Drop-In Visits, Dog Walking
5.0
46 reviews
14 repeat clients
from
$80
per night

Mango had a blast with Madison? She kept me updated the whole stay and I was not worried one bit.

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Sitter Profile Image: Candice B.
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Sitter Profile Image: Candice B.
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7.

Candice B.

Just waiting to play fetch!
Chicago, IL, 60611
House Sitting, Drop-In Visits, Dog Walking
5.0
44 reviews
16 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!

Sitter Profile Image: Ciera B.
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Sitter Profile Image: Ciera B.
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8.

Ciera B.

1 year of experience/ vet tech
Chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking
4.5
23 reviews
13 repeat clients
from
$27
per night

Absolutely the best!!! She took such wonderful care of my puppies while I was out of town and made my trip such a relief because I knew my little babies were in great hands. She sent videos, photos and updates thought out the day and was amazing! 10000/10 recommend ??

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Sitter Profile Image: Rebecca A.
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Sitter Profile Image: Rebecca A.
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9.

Rebecca A.

Rebecca from Jenny B. farm
Lincoln Park, Chicago, IL, 60614
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
52 reviews
17 repeat clients
from
$50
per night

Rebecca was great. Very reliable. Excellent communication. She sent lots of pictures and I could see she was taking very good care of my kitty. She has a very cute personality, too!

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Sitter Profile Image: Sarajane P.
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Sitter Profile Image: Sarajane P.
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10.

Sarajane P.

Loving your pets like my own
Lake View, Chicago, IL, 60657
House Sitting, Drop-In Visits, Dog Walking
5.0
20 reviews
9 repeat clients
from
$80
per night

Another great house sitting experience! Lots of pictures and updates every day. Sarajane takes great care of my dog and apartment while I’m away; would definitely recommend.

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Sitter Profile Image: Natalie N.
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Sitter Profile Image: Natalie N.
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11.

Natalie N.

Nursing Student and Animal Lover
Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking
5.0
17 reviews
5 repeat clients
from
$125
per night

Natalie was so wonderful with our elderly diabetic pup. We felt so at ease leaving him with her for the weekend and she took such great care of him. Her communication and updates were lovely! Can’t wait to have her back!

Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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12.

Emily N.

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

Emily was amazing! She was very accommodating with my weird flight schedule and my dogs were so happy to be with her. She also kept my home nice and tidy!

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Sitter Profile Image: Melanie R.
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Sitter Profile Image: Melanie R.
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13.

Melanie R.

Trustworthy petsitter, cats & dogs!
Chicago, IL, 60647
House Sitting, Drop-In Visits, Dog Walking
5.0
95 reviews
32 repeat clients
from
$45
per night

Melanie has been awesome, house sitting for us several times, taking excellent care of our pup, and leaving our house perfect for our return home. She's been very thoughtful, with great communication, and sharing photos. We highly recommend her.

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Sitter Profile Image: Caren A.
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Sitter Profile Image: Caren A.
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14.

Caren A.

Affected By Recent Layoffs 💻🥲
Chicago, IL, 60610
House Sitting
5.0
51 reviews
26 repeat clients
from
$70
per night

Caren was so kind and easy to work with. She was extremely communicative throughout and truly seemed to enjoy watching our two cats. She left our house exactly as we had left it. We would 100% love to have Caren house sit again!

Sitter Profile Image: Samantha H.
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Sitter Profile Image: Samantha H.
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15.

Samantha H.

Musician and Dog Lover
Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
32 reviews
12 repeat clients
from
$60
per night

Samantha watched my 1 year Golden Retriever for 3 days while I was out of town for a wedding and I couldn't have asked for a better experience! She sent me updates (including adorable pictures) and made me feel assured that my pup was getting the best care! She kept my space clean and even ran the dishwasher for me before she left! 10/10 recommend Samantha! I will certainly be booking again!

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Sitter Profile Image: Cheryl L.
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Sitter Profile Image: Cheryl L.
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16.

Cheryl L.

Fun-loving music teacher loves pets
West Town, Chicago, IL, 60622
House Sitting, Drop-In Visits, Dog Walking
5.0
31 reviews
11 repeat clients
from
$65
per night

Cheryl was great. She took wonderful care of our pup, was easy to communicate with and flexible to our schedule. I’d absolutely recommend her for any dog-sitting needs in the future.

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Sitter Profile Image: Tamara S.
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Sitter Profile Image: Tamara S.
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17.

Tamara S.

Available daily.Geniune care.Active
Chicago, IL, 60610
House Sitting, Drop-In Visits, Dog Walking
5.0
25 reviews
7 repeat clients
from
$75
per night

Tamara was great with my dog and cat! She sent lots of pictures and kept me updated how they were in my absence. I would recommend her to any pet parent.

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Sitter Profile Image: Federico C.
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Sitter Profile Image: Federico C.
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18.

Federico C.

"Pawfect Dog Walks Guaranteed!"
Chicago, IL, 60647
House Sitting, Drop-In Visits, Dog Walking
5.0
9 reviews
3 repeat clients
from
$120
per night

Federico was amazing when watching my (very large) dog Duke for a long weekend! He was super communicative, sent lots of pictures and videos, and made sure Duke got plenty of walks and playtime throughout my whole trip. I would definitely recommend Federico!

Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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19.

Jasmine P.

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

Jasmine was amazing yet again with my dobie, Storm. I had some last minute emergency changes to my trip and her flexibility and understanding really put me at ease during a stressful time, I'm so grateful for her support! Super communicative, Jasmine took great care of my girl and my place too. Also, Storm is reactive to other dogs and I trust Jasmine to know how to deal with that. Highly recommend.

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Sitter Profile Image: Sophie R.
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Sitter Profile Image: Sophie R.
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20.

Sophie R.

South Loop Based Pet Lover!
Chicago, IL, 60605
Boarding, House Sitting, Drop-In Visits
5.0
35 reviews
11 repeat clients
from
$50
per night

Sophie was wonderful with our girls! She was very attentive to their specific needs and was very communicative and reliable. We recommend her to anyone looking for a cat sitter, thanks Sophie!

Search Map


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