House Sitting in 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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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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1. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
118 reviews
36 repeat clients
from
$55
per night
Profile image

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!!

Sitter Profile Image: Kaitie G.
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Sitter Profile Image: Kaitie G.
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2. Kaitie G.

Star Sitter
Miss Rachel for pets 🐾 she/her(s)
West Town, Chicago, IL, 60622
4.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
9 repeat clients
from
$75
per night
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Katie is fantastic!! Very friendly and communicative, and as a bonus, takes awesome photos of your pet! We loved having her house-sit and take care of our very extroverted cat. Highly recommend!

Sitter Profile Image: Lindsay J.
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Sitter Profile Image: Lindsay J.
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3. Lindsay J.

Star Sitter
Cat mom and animal lover
Chicago, IL, 60642
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
45 reviews
10 repeat clients
from
$64
per night
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Lindsey is wonderful! She took great care of a cats and our place while we were traveling. She was great at keeping us in the loop and making us aware of any issues. She'll be our go to cat sitter!

Sitter Profile Image: Megan W.
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Sitter Profile Image: Megan W.
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4. Megan W.

Star Sitter
Megan W. Of Chicago area
West Town, Chicago, IL, 60622
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
61 reviews
17 repeat clients
from
$65
per night
Profile image

Highly, highly recommend Megan! Megan cared for our dog, like he was her own for the last week. She sent tons of pictures along the way, so we could see he was happy! She took him on adventures (which we said was great to do), walks, and lots of cuddles. She also helped with a shipment of frozen dog food that was supposed to arrive before we left. Our dog was sad to see her leave. We’ll definitely use Megan again!

Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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5. Otis B.

Dog's Best Friend
Near West Side, Chicago, IL, 60612
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
25 repeat clients
from
$65
per night
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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!

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

Star Sitter
In a bind? I’d love to help!
West Town, Chicago, IL, 60482
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
78 reviews
30 repeat clients
from
$90
per night
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Ann was great with my dog Lucy! She kept me updated via photos throughout the day and little fun comments. Ann was attentive and connected very well with my dog.

Sitter Profile Image: Eduardo N.
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Sitter Profile Image: Eduardo N.
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7. Eduardo N.

Loving Care When You’re Not There
Chicago, IL, 60654
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
4 repeat clients
from
$45
per night
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Eduardo did a wonderful job watching Obi! Our neighbors commented that it seemed like Obi seemed to be out often with him and they seemed to have fun adventures together. When we came home, he had left the place just as clean as we left it, including washing our sheets for us.

Sitter Profile Image: Munder S.
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Sitter Profile Image: Munder S.
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8. Munder S.

Star Sitter
Your pet needs some me time too
West Town, Chicago, IL, 60642
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
130 reviews
47 repeat clients
from
$66
per night
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Munder kept us updated with cute photos and was so great. Our vacation was better because we had no worries about our pets with Munder taking care of them!

Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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9. Saniah I.

Star Sitter
Saniah: Your pets, my love!
Chicago, IL, 60605
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$50
per night
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Saniah is great! She was on time and clearly showed that she cares for animals, asking about our dog’s favorite toys and treats. I felt entirely comfortable leaving our dog with her in our home and we will be using her again!

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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10. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60616
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$65
per night
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Crystal responded to my cat sitting request quickly, asked great questions, followed all directions, and my kittens loved her. I will definitely try to book with her in the future!

Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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11. Allison J.

Star Sitter
Previous Veterinary Technician
Near West Side, Chicago, IL, 60608
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
24 repeat clients
from
$80
per night
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Allison did a great job watching Penelope. Kept me in the loop with her care, responded in a timely fashion & left my house cleaner then when I left. Will for sure be using her in the future!

Sitter Profile Image: Taylor M.
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Sitter Profile Image: Taylor M.
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12. Taylor M.

Rover 101
Loving, meticulous sitter!
Loop, Chicago, IL, 60001
1.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
19 reviews
7 repeat clients
from
$50
per night
Profile image

Taylor is a DREAM dog sitter! She exceeded every single expectation by a landslide and left me with zero worries. Taylor was incredibly communicative, sent tons of sweet updates, and genuinely cared about my pup while I was out of town. I could tell in pictures and videos that my pup was having the best time, getting lots of snuggles, and was calm. She even gave my pup a bath before leaving! Taylor also exceeded expectations by taking excellent care of my apartment. On top of Taylor being completely wonderful, her two pups, Sunny and Leo, were adorable and played really well with my dog. I can’t recommend Taylor enough!

Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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13. Nicole C.

WFH, responsible, reliable 🧘🏻‍♀️
Near South Side, Chicago, IL, 60616
1.2 mi. away
Boarding, House Sitting
5.0 out of 5 stars
16 reviews
2 repeat clients
from
$72
per night
Profile image

Nicole went above and beyond what we could've asked for from a sitter. She stayed at our place for a week and looked after our two boys. Our youngest Vinny had started to have a little bit of diarrhea before we left for vacation, but we thought it would pass with some water and a few extra potty breaks. A few days into her stay, it was apparent it was getting worse, so we got in contact with our vet and arranged for testing and meds. Nicole handled everything with the vet and the boys so fast, and was so communicative and organized. And I know Vinny - he's a handful on his own, but with a tummy ache, you need to keep your eyes on him 24/7, and she did just that. I'm so thankful to have had someone take care of him the way I would. We also have this little ritual we keep with our pup Rusty's memorial (he passed a year ago). She kept up our little routine and gave us updates on him too :) We just off-handedly told her it was a thing we do, and the fact that she kept it up meant so much. I could ramble on forever! Bottom line, Nicole is an exceptional sitter/person and I would 10000% trust her with my boys again.

Sitter Profile Image: Reshunda B.
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Sitter Profile Image: Reshunda B.
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14. Reshunda B.

Paws-itively
South Lawndale, Chicago, IL, 60608
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
3 repeat clients
from
$30
per night
Profile image

Reshunda was prompt and attentive to our care instructions for our special needs pets. She’s a great sitter and I definitely will be booking with her again!

Sitter Profile Image: Jasmine V.
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Sitter Profile Image: Jasmine V.
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15. Jasmine V.

Rover 101
Star Sitter
Animal lover! :)
Lower West Side, Chicago, IL, 60608
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$60
per night
Profile image

Jasmine is amazing with dogs. Our pups love her. When she came to visit them they remembered her from the last sit, even though it was only a few hours, and got super excited. That says everything. She communicates well with updates every morning & evening and lots of photos. During a walk our neighbors large dog got loose & tried to attack our dogs. Jasmine physically defended our small dogs against the bigger one and got them to safety. Above and beyond care. Jasmine let us know immediately what happened. You can trust she will do everything in her power to keep your pups safe & happy.

Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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16. Johnathan W.

A friend that cares
Loop, Chicago, IL, 60642
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
15 repeat clients
from
$88
per night
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Johnathan is great! Our dog felt immediately comfortable with him and they had a great time together. He was communicative and really great all around.

Sitter Profile Image: Amanda J.
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Sitter Profile Image: Amanda J.
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17. Amanda J.

Star Sitter
Graduate student who loves animals!
Chicago, IL, 60607
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
11 repeat clients
from
$50
per night
Profile image

I was going abroad and my friends watching my 7 month old puppy had a 2 day gap. Tyko had only

Sitter Profile Image: Becca C.
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Sitter Profile Image: Becca C.
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18. Becca C.

Looking for pups to take care of!
Near West Side, Chicago, IL, 60607
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
5 repeat clients
from
$45
per night
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Snoopy loves spending time with Becca. I can see his excitement in the update pictures I receive! I appreciate the open communication, flexibility and consistency. :)

Sitter Profile Image: Callie L.
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Sitter Profile Image: Callie L.
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19. Callie L.

I love caring for animals!!
Near West Side, Chicago, IL, 60607
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
6 repeat clients
from
$50
per night
Profile image

We were gone a week and knew our Marley and house were in great hands. We have had Callie come see our baby several times before and this time house sit and we don't want to have anyone else take care of her. Our house was well taken care of and my girl is happy, what else could we ask for. I am a hover Mom and Callie just rolled with it and let me know she was doing fine and sent pics and I was able to relax. We can't thank you enough. Callie.

Sitter Profile Image: Marlena H.
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Sitter Profile Image: Marlena H.
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20. Marlena H.

Star Sitter
Shelter-animal trained pet sitter
Near West Side, Chicago, IL, 60607
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
8 repeat clients
from
$50
per night
Profile image

Marlena was flexible and responsive. Our dog was relaxed when we returned home later than scheduled and it was apparent that he had fun hanging out with her. We hope to be able to schedule her for dog sitting again in the future!

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Chicago House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Chicago are rated on average 4.9 out of 5 stars based on 17,944 reviews.

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Rover also offers House Sitting in:

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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