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
35 repeat clients
from
$55
per night
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Emily is great! She checked in often and took excellent care of Maeve and McKenna - we look forward to working with her again soon and will definitely recommend her to friends.

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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
22 reviews
10 repeat clients
from
$75
per night
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Kaitie was amazing with Sasha! I had lots of picture updates and great communication. Sasha clearly had a great time and enjoyed all her walks. Kaitie left the house cleaner than when she showed up and was a really great guest. I highly recommend her! Thank you!

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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!

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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
62 reviews
17 repeat clients
from
$65
per night
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Megan is so patient and kind when she dog-sat in our apartment. We have two dogs and one is challenging to deal with. Barks at strangers, doesn't want to be touched, etc. Megan totally knew how to handle it and rolled with the punches. The pups were happy and tired when we got home. Can;t wait to book Megan again.

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Sitter Profile Image: Pablo V.
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Sitter Profile Image: Pablo V.
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5. Pablo V.

Rover 101
Fun walks
Chicago, IL, 60642
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
243 reviews
96 repeat clients
from
$66
per night
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Pablo was wonderful with our Dalmatian! She can be a handful, and he was great! Very attentive to her and took care of her just as we would. Would definitely recommend him to anyone

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Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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6. Belicia K.

Star Sitter
Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
7 repeat clients
from
$50
per night
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Belicia is the absolute best. We were gone for two weeks for our wedding abroad and were so busy that we barely had time to check in the way we normally would. Yet, Belicia made a daily effort to give us the loveliest updates about her time with our girl, giving us total peace of mind.

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Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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7. 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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I highly recommend Otis as a Rover sitter! He was very punctual and professional during our meet and greet. During his stay in my home, he followed all instructions - including correctly using a type of leash that was new to him - and sent lots of updates and photos. I will definitely book Otis again in the future!

Sitter Profile Image: Ann Marie M.
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Sitter Profile Image: Ann Marie M.
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8. 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 Marie helped watch our puppy while we were traveling and she was amazing! Sent great updates and pictures and took great care of our girl.

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Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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9. 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
42 repeat clients
from
$65
per night
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Crystal did an absolutely wonderful job taking care of our senior dog. She went above and beyond to make sure our Ollie was happy and well taken care of. She sent pictures and updates daily. We plan to use her services again, and highly recommend her!!

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Sitter Profile Image: Munder S.
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Sitter Profile Image: Munder S.
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10. 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 was great and communicative when housesitting for me. I had just moved to the area and was nervous leaving my dogs with someone as they had moved across country to a new environment but Munder did a great job taking care of my dogs and cat while I was away. 10/10

Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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11. 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!

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Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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12. 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 took excellent care of my dog and sent me updates throughout the stay. She was flexible when the exact dates changed a couple times and great about coming to do two meet and greets to help me feel comfortable. I could tell my dog had lots of fun with her, and the place looked nicer than when I left (she even tidied up). I’ll definitely be booking Allison again.

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Sitter Profile Image: Reshunda B.
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Sitter Profile Image: Reshunda B.
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13. 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
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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: Araceli G.
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Sitter Profile Image: Araceli G.
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14. Araceli G.

caring & responsible pet sitter
Near West Side, Chicago, IL, 60607
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
26 reviews
7 repeat clients
from
$50
per night
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Araceli is the best!! My dog was recovering from an injury and needed to be watched closely and given medicine while we were gone and she went above and beyond to make sure he was resting and healing and that I felt reassured while being away. She even picked up more medicine when needed. She was responsive and flexible as our travel plans changed. Araceli will take the absolute best care of your pet! She makes a stressful situation much less. Can’t recommend her enough!!

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Sitter Profile Image: Taylor M.
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Sitter Profile Image: Taylor M.
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15. 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
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Taylor was so wonderful with my pup! She was communicative, took him for lots of walks, and kept me updated through the day. My puppy also seemed in great spirits when I returned home!

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Sitter Profile Image: Jasmine V.
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Sitter Profile Image: Jasmine V.
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16. 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
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Jasmine was terrific! Kept me updated on my girl, Reese, and took such great care of her. Would definitely book Jasmine when I go on a trip again.

Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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17. 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
37 reviews
15 repeat clients
from
$125
per night
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Johnathan did an amazing job watching our pup for a week while we went to Mexico. We didn’t have service so Johnathan sent email updates with the best pictures of Buddha which was perfect. This was our first time booking with him and we will definitely be using him for our future travels. He went above and beyond and we are so happy we found him!

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Sitter Profile Image: Callie L.
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Sitter Profile Image: Callie L.
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18. 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
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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.

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Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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19. 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 is awesome. She stayed with our pups over 6 days in our home. She followed all our instructions and treated the pups like her own. She catered to their individual personalities and needs. Awesome communication and lots of photos. Nicole continued caring for the dogs even though she got sick that weekend. She left our place spotless. Highly recommend!

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Sitter Profile Image: Amanda J.
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Sitter Profile Image: Amanda J.
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20. 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

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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.

Check out the House Sitting in your neighborhood:

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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