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: Lindsay J.
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Sitter Profile Image: Lindsay J.
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1. 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: Emily N.
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Sitter Profile Image: Emily N.
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2. 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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3. 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
24 reviews
11 repeat clients
from
$75
per night
Profile image

Kaitie was great! She is lively and lovely, and was so good with our puppy Laika. Laika has a lot of energy and was very much showing off for Kaitie but she took it in stride and was so patient with him. She took him for a long, long walk and knew exactly how to get him to listen. She's fine tuned her 'system' with how best to care for dogs, with her cool belt that she takes on walks with dogs to her efficient treat bag. You can tell she is super comfortable and confident in what she does. She was also an extremely respectful guest and was thoughtful about our no shoes in the house rule, cleaned up when she didn't have to and left soothing music on for Laika before she left the house. Would definitely have her back!

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
66 reviews
17 repeat clients
from
$70
per night
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This was not the first and not the last time I’ll have Megan watch my dog when I’m out of town. Megan is so great. She clearly has a passion and love for animals.

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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5. 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
99 reviews
43 repeat clients
from
$65
per night
Profile image

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!!

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

6. 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
26 repeat clients
from
$65
per night
Profile image

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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7. 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
80 reviews
30 repeat clients
from
$90
per night
Profile image

Ann Marie was a wonderful sitter with Smitty and Scout. She was interested in learning the details of their care, took time to get to know them, and made me feel confident that our dogs were in good hands while we were away. She was very easy to communicate with and sent lots of pictures during the stay. She was great! We will ask her to sit again!

Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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8. 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 was great as always! There’s often something going on with one of our pups, whether it’s skin allergies or an injury, and she’s so great with them. Her experience as a vet tech gives us a lot of comfort when these things come up, she has the knowledge and truly cares about our dogs’ best interest. Thanks again, Allison!

Sitter Profile Image: Taylor M.
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Sitter Profile Image: Taylor M.
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9. 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 just watched my pup at my apartment for the 2nd time and it’s safe to say she’s my new go-to! Each time I come home after she spends time with Taylor, my pup is so calm and in a great mood. Taylor has been so consistent and above and beyond in every aspect. I had zero worries about my pup while I was out of town and I owe it all to her. On top of her exceptional care, I can tell that our pups are getting even more comfortable together! The videos of them playing keep getting cuter.

Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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10. Nicole C.

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

Nicole was so great! Updated us with photos of Ernie, took him to the park and made sure he got lots of hangout time. We came back to a clean house and a very happy, relaxed dog. We would definitely use Nicole again!

Sitter Profile Image: Jasmine V.
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Sitter Profile Image: Jasmine V.
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11. 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
23 reviews
6 repeat clients
from
$60
per night
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Jasmine kept my dog and cat over a long weekend and stayed in my home. She was polite, kept me updated often with notes and photos, she was prompt in our meeting and left my house spotless. Most importantly - my pets were well cared for and happy when I returned. 100% would book again!

Sitter Profile Image: Araceli G.
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Sitter Profile Image: Araceli G.
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12. 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
29 reviews
8 repeat clients
from
$50
per night
Profile image

My dogs had a great time with Araceli! She watched my dogs in my home for a weekend and sent lots of updates. She was very responsive when I checked in. House was left tidy :)

Sitter Profile Image: Callie L.
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Sitter Profile Image: Callie L.
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13. 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

Callie was extremely communicative since day 1 of reaching out to her, we did a meet and greet and the dogs seemed instantly bonded with her and she asked a bunch of questions to really get to know their schedules and personalities. During our stay she provided us with updates and pictures and when we came home the house was spotless and the dogs were so happy. She is an extraordinary caretaker and even more talented artist! I’m so glad we went this route instead of the dog hotel this time around because my dogs are so much happier and healthier because of Callie. Anytime I had a special request she was there to help me out. Thank you so much.

Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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14. 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
Profile image

Arrived in time and take care of my dog perfectly, great communication all the time, definitely recommend her and super happy with the service provided.

Sitter Profile Image: Reshunda B.
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Sitter Profile Image: Reshunda B.
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15. 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
6 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: Natalie R.
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Sitter Profile Image: Natalie R.
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16. Natalie R.

Intuitive & Empathic Dog Lover
Chicago, IL, 60612
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
9 repeat clients
from
$65
per night
Profile image

Natalie was absolutely wonderful. She called in advance to be prepared on what exactly the needs were. She was flexible in her timing and drove all the way to my place even while storming. My dog loved her instantly and even ate while I was away (speaks to the level of comfortability she must ve felt.). Would absolutely use her services again and couldn't sing higher praises.

Sitter Profile Image: Rhiannon G.
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Sitter Profile Image: Rhiannon G.
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17. Rhiannon G.

Responsible, solo sitter
Chicago, IL, 60604
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$50
per night

Rhiannon was an excellent choice for us. She was flexible, self-sufficient, and left our place perfectly in order. Our dog was well-cared for in our absence. Highly recommend!

Sitter Profile Image: Janette V.
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Sitter Profile Image: Janette V.
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18. Janette V.

People call me Snow White lol
Chicago, IL, 60609
1.8 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$65
per night
Profile image

So happy to have connected with Janette. She took the time for a meet and greet, asked lots of questions about our boy’s routine and sent us plenty of updates when she watched him. Janette took special care to take our boy on walks to keep him distracted when he got anxious. Our senior pup was nice and relaxed when we got home. She’s a true animal lover!

Sitter Profile Image: Sarah C.
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Sitter Profile Image: Sarah C.
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19. Sarah C.

Rover 101
I’ll make your dog feel at home 💜
Lower West Side, Chicago, IL, 60608
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
52 reviews
20 repeat clients
from
$65
per night
Profile image

Sarah and Zach were amazing. It was our first time leaving our dog and they were so patient and kind. Incredibly accommodating when we had changes in plans willing to drop our dog off and pick her up. I loved how they sent pictures and updates almost every day. I felt so comfortable leaving my girl with them and would have her stay with them again anytime. Truly amazing people!

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
32 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.

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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