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

Emily was, as usual, an AMAZING dog sitter for Finn for the week we were gone. She is kind, attentive, and professional. She plays with Finn and sends detailed updates. She was very flexible and updated us via WhatsApp because we were out of the country. We will always come to her first if we need a sitter for Finn!

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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
20 reviews
8 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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Lindsay was awesome with our dachshund Beau who has serious separation anxiety which means a lot of very specific instructions for how to leave the house when she's away. She was thorough and left the house in great condition. Will definitely be booking with her again!

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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
60 reviews
17 repeat clients
from
$65
per night
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Megan was great with barrel. Barrel is a little timid with new sitters but Megan gave her space to come out on her own. Once barrel opened up, she was very playful and had a great time.

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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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Otis did a great job with Bonita, she was happy and healthy after 15 long day away. There was lack of communication but overall I recommend him to take care of your doggy.

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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
29 repeat clients
from
$90
per night
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Ann Marie was fantastic! She took care of our neurotic French Bulldog and two cats for five days, and house sat while we were away. Our dog is on several medications and needs some special care. Ann Marie took great care of all three babies, sent regular photo updates, and left our house immaculate. Thank you, will book her again!

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Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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7. 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: Eduardo N.
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Sitter Profile Image: Eduardo N.
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8. 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.

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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
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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.

Confirmed availability: Memorial Day Weekend
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, 60653
2.5 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!

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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 was amazing. This was my first time leaving my dog with someone other than family, and Allison made me feel so comfortable. My dog seemed to love her, and she left my apartment as clean or cleaner than when I left! I would 100% recommend Allison and will plan to book her again in the future!

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Sitter Profile Image: Reshunda B.
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Sitter Profile Image: Reshunda B.
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12. 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
1 repeat client
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!

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Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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13. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
5 repeat clients
from
$33
per night
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Elizabeth was so great! We were able to meet before the house sitting and went over the specifics of my dog. She gave me daily updates and let me know he was doing well which I really appreciated!! I would definitely book again ?

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Sitter Profile Image: Jasmine V.
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Sitter Profile Image: Jasmine V.
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14. 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.

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Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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15. Nicole C.

WFH, responsible, reliable 🧘🏻‍♀️
Near South Side, Chicago, IL, 60616
1.2 mi. away
Boarding, House Sitting
5.0 out of 5 stars
15 reviews
2 repeat clients
from
$72
per night
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Nicole was phenomenal with my big, excitable, very opinionated pitbull - Juniper. I was gone for a full week and it was the first time I’d met Nicole. We did a meet and greet and she asked fantastic questions. She checked in a few days before my trip and arrived right on time the day I flew out. Throughout the week I was comforted by little updates and FANTASTIC pictures of Juni (honestly I don’t know how she did it because I haven’t been able to get a good pic out of Juni in months). She asked good questions throughout the week when needed and was super communicative. I got my times mixed up on the Rover app in regards to when I’d be returning and Nicole stopped by the house outside of the agreed upon times to make sure June got her dinner and a final pee. She also changed my bedsheets and folded my laundry??? Truly above and beyond - Juni (and my home and space) were well taken care of. Cannot recommend Nicole enough!

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Sitter Profile Image: Callie L.
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Sitter Profile Image: Callie L.
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16. 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
5 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.

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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
30 reviews
11 repeat clients
from
$50
per night
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I was going abroad and my friends watching my 7 month old puppy had a 2 day gap. Tyko had only

Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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18. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60607
1.7 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
44 reviews
12 repeat clients
from
$48
per night
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Deven is great! He took care of Lilith for more than 3 weeks and kept us updated regularly. He sent photos and FaceTimed us, took her on walks and got her pup cups. Made our time away from our baby better and less worrisome. We definitely recommend Deven! He even stayed late on the last day cause my flight was delayed and I needed him to take care of Lilith a bit more.

Sitter Profile Image: Araceli G.
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Sitter Profile Image: Araceli G.
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19. 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!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Salena V.
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Sitter Profile Image: Salena V.
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20. Salena V.

Will love your babies as my own
Chicago, IL, 60608
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$60
per night

Salena took care of my dog Taffy. It was such a relief to have someone I trusted and he loved when she took care of him and as he aged he let her put meds in his eyes and wiping him down without being a grouchy old dog.

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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