House Sitting In Near South Side Chicago

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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
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5.0 out of 5 stars
58 reviews
13 repeat clients
Profile image

Lindsay was great we needed a very last minute sitter, and she was able to make a miracle happen. Our dog has separation anxiety, and he was completely at ease when we came home. We will definitely be using Lindsay again to watch our dog.

Availability updated yesterday
Sitter Profile Image: Klara J.
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Sitter Profile Image: Klara J.
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2. Klara J.

Life long animal lover!
Near North Side, Chicago, IL, 60610
3.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
5.0 out of 5 stars
45 reviews
13 repeat clients
Profile image

Klara was great with my dog and she sent daily updates and photos. I highly recommend her and will use her house sitting services again. Thanks Klara!

Availability updated today
Sitter Profile Image: Nicole R.
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Sitter Profile Image: Nicole R.
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3. Nicole R.

Lovable reliable & trustworthy!
Bridgeport, Chicago, IL, 60616
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
Profile image

This our first time hiring someone to take care of our dogs, usually we leave them with family. This time the entire family was on a trip so we opted for Rover and feel very blessed to have found Nicole. Nicole is very detail-oriented, communicated perfectly and even sent videos twice a day. We decided to leave the dogs at home instead of sending them to an unknown environment. And she not only walked them. She sat with them and gave them attention. This all became very crucial because it was very hard for me to leave my dogs this time around. One of my dogs had a bit of an eye irritation and she did a great job keeping track of his progress and keeping me updated. We are very grateful for Nicole and will definitely ask for her services again in the future.

Availability updated today
Sitter Profile Image: Sarah M.
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Sitter Profile Image: Sarah M.
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4. Sarah M.

We’ll have fun in the paw-ffice!
Chicago, IL, 60612
4.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$57
per night
5.0 out of 5 stars
45 reviews
14 repeat clients
Profile image

Sarah was great! I have a Staffy/ Golden Retriever mix who is very needy and anxious. Sometimes he won't eat for a few days when left with somebody else, but he was eating on day 2. Sarah took him for long walks and took him to the park to sit outside for awhile (my pup loves to sunbathe!). She was very communicative. I live in a very dog friendly neighborhood and I heard from a few neighbors that they saw Sarah walking my dog and had nice to say about her and how relaxed my dog seemed with her. I will definitely book her again!

Availability updated today
Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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5. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60608
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
57 reviews
16 repeat clients
Profile image

Deven was professional and responsive from the first time I reached out to schedule a dog sitter. He was great both my puppy and older dog and comfortable providing oral, topical, and injection medications for my dog. Would highly recommend his services and will definitely be using again.

Availability updated 2 days ago
Sitter Profile Image: Pablo V.
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Sitter Profile Image: Pablo V.
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6. Pablo V.

Rover 101
Star Sitter
Fun walks
Chicago, IL, 60642
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$66
per night
5.0 out of 5 stars
279 reviews
106 repeat clients
Profile image

Pablo stayed at our home for over a week to watch our dog Bently and we were so impressed. He went above and beyond and Bently absolutely loved him. He provided us with frequent updates, took care of our plants and cleaned up a mess when Bently got sick. We would strongly recommend Pablo for anyone considering him.

Availability updated 4 days ago
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
3.0 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$88
per night
5.0 out of 5 stars
95 reviews
35 repeat clients
Profile image

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!

Availability updated 6 days ago
Sitter Profile Image: Emily B.
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Sitter Profile Image: Emily B.
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8. Emily B.

Experienced Corgi dog mom!
Chicago, IL, 60661
2.0 mi. away
Boarding, House Sitting, Drop-In Visits
from
$50
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
Profile image

Emily was so wonderful and kind! She sent frequent updates, administered our cat’s 3x daily medicine, and even got our rather aloof cat to loosen up around her! I highly recommend her for pet sitting. Thank you Emily!

Availability updated yesterday
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
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$68
per night
5.0 out of 5 stars
116 reviews
49 repeat clients
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!!

Availability updated 5 days ago
Sitter Profile Image: Margo K.
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Sitter Profile Image: Margo K.
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10. Margo K.

Animal lover living in Bridgeport!
Bridgeport, Chicago, IL, 60608
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
4.5 out of 5 stars
8 reviews
Profile image

Margo did a great job. She was flexible and responsive. She sent lots of pictures and updates of our cats. We returned home after a week-long vacation and the house was in excellent shape. I will definitely use her for house-sitting and drop-in services in the future.

Availability updated 12 days ago
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
from
$45
per night
5.0 out of 5 stars
28 reviews
6 repeat clients
Profile image

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 ?

Availability updated yesterday
Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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12. Emily N.

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

Availability updated 5 days ago
Sitter Profile Image: Nico M.
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Sitter Profile Image: Nico M.
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13. Nico M.

Caring for your pet like my own
Chicago, IL, 60605
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
19 reviews
2 repeat clients
Profile image

Nico took care of my puppy for a few hours and did a such a nice job. He seems really patient and kind. I came home and Nico had followed all my directions and made really good choices with my pup. Highly recommend him and I would hire him again.

Availability updated today
Sitter Profile Image: Connie C.
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Sitter Profile Image: Connie C.
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14. Connie C.

Star Sitter
Responsible, attentive animal lover
Chicago, IL, 60616
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
Profile image

Connie was communicative and easily bonded with our dogs! She also sent pictures of them! I felt comfortable leaving my dogs with her and knew they were in good hands. Thank you for taking care of our dogs! Came back to happy puppies!

Availability updated 4 days ago
Sitter Profile Image: Katie "Anni" W.
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Sitter Profile Image: Katie "Anni" W.
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15. Katie "Anni" W.

Star Sitter
Need work from home companions!
Near South Side, Chicago, IL, 60616
0.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$53
per night
5.0 out of 5 stars
35 reviews
13 repeat clients

I have booked her multiple times for my dogs when I go on vacation and business trips. She always makes them feel comfortable right away and I can tell they are having a good time when I see their pictures together. I would recommend her to anyone trying out Rover!

Availability updated today
Sitter Profile Image: Willard Bryan K.
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Sitter Profile Image: Willard Bryan K.
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16. 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
from
$80
per night
5.0 out of 5 stars
24 reviews
4 repeat clients
Profile image

I don’t even know where to begin! Willard took such good care of my senior pup. I have a lot of anxiety around being away from my dog and Willard was able to put me ease. He provided plenty of pics and updates and had a quick response time. And, when I returned from my trip, I found a lovely printed photo of my dog that Willard took during his time as my sitter. Looking forward to booking again in the future!

Availability updated 6 days ago
Confirmed availability for Thanksgiving
Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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17. Allison J.

Star Sitter
Previous Veterinary Technician
Chicago, IL, 60608
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$85
per night
5.0 out of 5 stars
66 reviews
25 repeat clients
Profile image

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!

Availability updated 17 days ago
Sitter Profile Image: Courtney G.
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Sitter Profile Image: Courtney G.
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18. Courtney G.

Star Sitter
A connection like a second mother!
Loop, Chicago, IL, 60605
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$90
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
Profile image

Courtney was professional, reliable, on-time, and shared tons of great photos of Whisky! She even updated me on an issue with my home while I was away which was so valuable in my absence. She went above and beyond my offering to help in anyway she could. Whisky was well taken care of and she was diligent about learning all of his unique quirks to provide him with unique care that fit his needs. Thank you SO much Courtney! Hope to have you back in the future.

Availability updated yesterday
Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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19. Otis B.

Dog's Best Friend
Loop, Chicago, IL, 60602
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5.0 out of 5 stars
69 reviews
30 repeat clients
Profile image

Otis was WONDERFUL. We couldn't have higher praise for him. We originally had another Rover scheduled for boarding, and she canceled on us 3 hours before we were supposed to head to the airport. Otis helped us last minute and arrived right on time to save us. Our Bernese Mountain Dog puppy is a highly energetic handful, and Otis kept her entertained and stimulated the entire weekend. Our dogs loved hanging out with him, and he was great about sending us picture updates throughout the day. The house was also in even better condition than when we left it. Otis was the best dog sitter and house guest, and we would 100% always book him if we could.

Availability updated 4 days ago
Sitter Profile Image: Maritza V.
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Sitter Profile Image: Maritza V.
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20. Maritza V.

Longtime Doggie Sister
Near South Side, Chicago, IL, 60605
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
Profile image

Maritza was amazing!! She sent updates on how our puppy was doing and she was very responsive overall. Highly recommend!

Availability updated 3 days ago

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  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

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Why Choose Rover?

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    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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