House Sitting In Near South Side 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: Kaitie G.
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Sitter Profile Image: Kaitie G.
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1. Kaitie G.

Star Sitter
Miss Rachel for pets 🐾 she/her(s)
West Town, Chicago, IL, 60622
4.8 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

Kaitie took great care of our pup and our home while we were away. She was communicative and shared plenty of photos which put us at ease so we could enjoy our trip. She made sure she had all of the important details about our dog's needs and was very thoughtful about her care. Usually our dog is a bit out of sorts after we've been away. This time he was is normal happy self when we got home which speaks volumes about how much he enjoyed Kaitie's visit :)

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Sitter Profile Image: Megan W.
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Sitter Profile Image: Megan W.
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2. Megan W.

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

Megan was an excellent sitter for my boys! I was able to leave my 2 boxers home while I travelled for a day long business trip. Megan sent pictures, notes and kept me informed throughout the day. I returned to 2 happy pups and a neat & tidy home. Thank you Megan!

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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
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
45 reviews
10 repeat clients
from
$64
per night

Lindsay is great! I travel regularly for work and she is always willing and able to accommodate the early departures and late arrival. She’s very respectful of my place and sends constant updates. My dog loves her and I book her regularly.

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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4. Emily N.

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

Emily has stayed in my home with my dogs many times now and she has always done an amazing job. Extremely trustworthy, clean, and my dogs are always well taken care of.

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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
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
25 repeat clients
from
$65
per night

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!

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Sitter Profile Image: Munder S.
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Sitter Profile Image: Munder S.
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6. Munder S.

Star Sitter
Your pet needs some me time too
West Town, Chicago, IL, 60642
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
129 reviews
47 repeat clients
from
$66
per night

Munder was awesome. Extremely kind, caring and respectful of our home and kitten while we were gone. He sent daily updates and was very communicative. We will definitely have him stay with our kitten again

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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
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
4 repeat clients
from
$45
per night

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: Saniah I.
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Sitter Profile Image: Saniah I.
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8. Saniah I.

Star Sitter
Saniah: Your pets, my love!
Chicago, IL, 60605
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$50
per night

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.

Confirmed availability: Memorial Day Weekend
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, 60653
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$65
per night

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: Taylor M.
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Sitter Profile Image: Taylor M.
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10. Taylor M.

Rover 101
Loving, meticulous sitter!
Loop, Chicago, IL, 60001
1.0 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

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!

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Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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11. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$33
per night

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: Willard Bryan K.
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Sitter Profile Image: Willard Bryan K.
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12. Willard Bryan K.

Star Sitter
Pet Buddy in the heart of Sloop!
Loop, Chicago, IL, 60605
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
2 repeat clients
from
$80
per night

Willard is an exceptional human being, evidenced by our dog’s immediate attraction to him. She was very happy to see him again the next evening, and so were we. When we return in the coming years, we will definitely contact Willard.

Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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13. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60607
2.0 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
44 reviews
12 repeat clients
from
$48
per night

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.

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Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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14. Nicole C.

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

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: Johnathan W.
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Sitter Profile Image: Johnathan W.
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15. Johnathan W.

A friend that cares
Loop, Chicago, IL, 60642
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
15 repeat clients
from
$88
per night

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: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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16. Ashleigh H.

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
0.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$30
per night

Ashleigh was great with my pups! I have two dachshunds - one is very energetic and the other has separation anxiety. She made sure to take them on lots of walks and give them lots of snuggles. Normally when I'm gone, they don't eat and I come home to two overly-clingy dogs. This time, they were well-fed and didn't really seem to care that I was home. She also sent lots of updates so I always knew how they were doing. Not only were my dogs happy, I also came home to a spotless house. I will definitely book Ashleigh again!

Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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17. Amanda B.

Headline incomplete
Loop, Chicago, IL, 60605
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
4 repeat clients
from
$35
per night

Amanda took such good care of my kitties and was very communicative! I got updates daily of how they were doing. My apartment was tidy when I got back. Great experience!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Amy C.
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Sitter Profile Image: Amy C.
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18. Amy C.

Animal enthusiast with extra ♥️
Chicago, IL, 60605
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
4 repeat clients
from
$60
per night

Amy was absolutely amazing with caring for our pets and their various needs. Very helpful, kind, and communicative. Couldn’t have asked for better care of our animals! Would highly recommend!

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Sitter Profile Image: Aqsa A.
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Sitter Profile Image: Aqsa A.
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19. Aqsa A.

Reliable and Trustworthy Cat Sitter
Near South Side, Chicago, IL, 60605
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
from
$30
per night

I’m so happy I was able to find Aqsa to take care of my kitty while I was away! She went above and beyond to make her feel cared for and always updated me with pictures. I would absolutely book her again!

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Sitter Profile Image: Kayla M.
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Sitter Profile Image: Kayla M.
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20. Kayla M.

Attentive & Patient Sitter
Chicago, IL, 60605
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$70
per night

Kayla was awesome! Super communicative on my first time doing a in-house sitting appointment. She seemed to get along well with my cat, and I’m so so grateful!

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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