House Sitting Uptown

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Over 1,582
pet parents in Uptown have booked house sitting

Uptown, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Vanessa S.
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Vanessa S.
from
$45
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
12 years of experience
Lincoln Square, Chicago, IL, 60640

Vanessa was absolutely incredible with our pup, Chico. She stayed at our home and took impeccable care of both Chico and the house while we were away, giving us complete peace of mind throughout the trip. She was so kind, friendly, communicative, and thoughtful, and we especially appreciated all of the updates and photos she shared while we were gone. It was clear Chico was happy, comfortable, and truly cared for the entire time. We honestly couldn’t have asked for a better experience and can only hope we’ll be lucky enough to use Vanessa again in the future.

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Scott H.
Sitter Profile Image: Jamie G.
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Jamie G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
59 reviews
16 repeat clients
32 years of experience
Uptown, chicago, IL, 60640

Jamie has a magic touch! Took great care of my anxious cat, whose normally quite shy around new people. I came home to a very cheerful kitty, and would highly recommend him for your fur baby.

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Charlie M.
Sitter Profile Image: Andre H.
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Andre H.
from
$50
per night
5.0 out of 5 stars
74 reviews
20 repeat clients
20 years of experience
Uptown, Chicago, IL, 60640

Andre was amazing! He dog sat my Berner, Pippa, for 3 days in my home. He managed to get my anxious pup to snuggle with him in a matter of hours, and sent me videos and pics throughout the stay. Thanks so much Andre!

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Susan W.
Sitter Profile Image: Kelly A.
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Kelly A.
from
$65
per night
5.0 out of 5 stars
34 reviews
6 repeat clients
28 years of experience
Uptown, Chicago, IL, 60613

This is Kelly’s second time watching our dogs for us. She stays at our house and leaves it cleaner than when she arrived. She follows all of the specifics that our dogs need including medication administration. She’s a clear communicator. One of our dogs has some behavioral issues and she’s done a great job supporting him!

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Lauren P.
Sitter Profile Image: Jakob C.
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Jakob C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
35 reviews
11 repeat clients
8 years of experience
Uptown, Chicago, IL, 60640

This was my second time having Jakob take care of my two dogs and a little bird while we were out of town. They seem to have a great time with him and he sends daily updates and pictures :) He is super respectful of the home and very punctual and responsible. Thanks again!

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Sofia & Collin E.
Sitter Profile Image: Gail B.
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Gail B.
Star Sitter
from
$64
per night
5.0 out of 5 stars
80 reviews
21 repeat clients
27 years of experience
Uptown, chicago, IL, 60640

Gail was incredible! So sweet. She was punctual, did great with keeping our puppy on her schedule and playing with her and administering some meds to our puppy. We will definitely try to book Gail again!

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Kylie C.
Sitter Profile Image: Drew B.
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Drew B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
32 reviews
4 repeat clients
9 years of experience
Chicago, IL, 60640

This was our first time working with Drew, and he was a great help for our long weekend away. The pups were happy, the house was clean upon our arrival home, and he was communicative throughout the long weekend to keep up us updated on everyone's well being.

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Jeremy H.
Sitter Profile Image: Anna J.
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Anna J.
from
$65
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
5 years of experience
Uptown, Chicago, IL, 60640

Anna was great with our pets! We were a little nervous to use Rover for the first time, but Anna offered us peace of mind as she sent us updates, pictures, and quick answers to any questions we had. We will definitely be reaching out again! Thank you, Anna, for your kindness and care with George and Barley!

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Andrew R.
Sitter Profile Image: Sky S.
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Sky S.
from
$50
per night
4.6 out of 5 stars
13 reviews
2 repeat clients
17 years of experience
Uptown, Chicago, IL, 60640

Sky took very good care of our dog Bisteca and our apartment. Bisteca is on the older side, takes a lot of meds, and it is very reactive, so he can be a handful. He was doing great when we came back from a 5-day trip, and the apartment was super tidy. Would definitely book again!

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Lucas C.
Sitter Profile Image: Luisa C.
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Luisa C.
Star Sitter
from
$63
per night
5.0 out of 5 stars
32 reviews
8 repeat clients
3 years of experience
Chicago, IL, 60614

Luisa was amazing! This was my first time leaving my puppy, and she did a great job providing updates, playing with my puppy, maintaining his schedule & came over before for a meet and greet. Super wonderful to work with.

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Brittany R.
Sitter Profile Image: Tammy G.
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Tammy G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
13 reviews
8 repeat clients
5 years of experience
North Center, Chicago, IL, 60613

Tammy is an amazing sitter, my pup Toby had a great time with her! She helped us out in an emergency/last minute situation and we are so grateful to have found her.

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Cassandra B.
Sitter Profile Image: Josephine B.
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Josephine B.
from
$60
per night
5.0 out of 5 stars
50 reviews
18 repeat clients
8 years of experience
Chicago, IL, 60660

Josie was exactly what we wanted for our dogs while we were away! She was so communicative with us and sent us so many pictures. We could tell our dogs loved her and cannot recommend her enough. It gave us so much peace knowing someone as loving as Josie was staying with our pups. We will definitely be using her again!

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Coursey E.
Sitter Profile Image: Rebecca K.
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Rebecca K.
from
$65
per night
4.9 out of 5 stars
88 reviews
39 repeat clients
15 years of experience
Uptown, Chicago, IL, 60613

Rebecca did a great job watching our house and our fur babies. It didn't even seem like they missed us. She sent pictures throughout the visit and communicated well. Thanks again.

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Joshua D.
Sitter Profile Image: Jasmin U.
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Jasmin U.
Star Sitter
from
$85
per night
5.0 out of 5 stars
43 reviews
17 repeat clients
6 years of experience
Uptown, Chicago, IL, 60640

Jasmin was amazing! Immediately our pups were calm around her and she was so attentive to their needs. We will definitely have her stay with our dogs again!

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Winifred G.
Sitter Profile Image: Angelique H.
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Angelique H.
Star Sitter
from
$32
per night
5.0 out of 5 stars
50 reviews
22 repeat clients
8 years of experience
Uptown, Chicago, IL, 60613

Angelique is a wonderful sitter, she kept me in the loop, took great pictures, and most importantly took great care of my pets who were happy and loved while i was gone

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Lauren V.
Sitter Profile Image: Duncan W.
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Duncan W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
19 reviews
6 repeat clients
13 years of experience
Lake View, Chicago, IL, 60657

Duncan was a professional and responsible caretaker. He went above and beyond our expectations when he took care of our 2 dogs Honey and Pickles for two weeks. Before even starting the job, he met us in a freezing blizzard for a simple meet + greet, which I think immediately showed his dedication to the job. He also cleaned up around our house when the dogs were making a mess, not something that we asked him to do — but rather something that he proactively did. One of our dogs, Honey, has anxiety. Duncan even stood overnight on New Years Eve just to help her stay calm during the fireworks, which I believe is something your average dog caretaker wouldn’t do! He was also very responsive with text and sent us updates every day. I felt much peace of mind because I knew Duncan was taking our two dogs on 2 walks every day, feeding them on time, and spending some time with them too. I would definitely recommend Duncan to a friend and would rebook him myself!

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Isaiah G.
Sitter Profile Image: Renee S.
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Renee S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
46 reviews
15 repeat clients
15 years of experience
Lincoln Square, Chicago, IL, 60625

Renee was great with our dog Winnie! She sent lots of photos, updates and was flexible on the timing of our sit. Winnie has some anxiety that Renee managed with patience and understanding. We will definitely have Renee sit for us again!

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Rachel S.
Sitter Profile Image: Doris C.
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Doris C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
12 years of experience
Uptown, Chicago, IL, 60640

Doris was wonderful! I’m so glad she was able to take care of my girls last minute. I got updates on all of my girls throughout the day. I’m so appreciative for her not only taking us on last minute but also while one of my girls is trying to recover from an upset stomach and requires a little more TLC. She’s one of the first sitters I’ve used using Rover, & the first time my pets were taken care of by someone other than friends and family and it was a great experience for us. I will definitely be reaching out to Doris again when I need a pet sitter.

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Reba B.
Sitter Profile Image: Megan B.
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Megan B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
15 years of experience
Lake View, Chicago, IL, 60613

Megan is absolutely wonderful! Not only did she take amazing care of our pup, she also left our home more spotless than when she arrived and helped take care of a lapse in our internet service while we were gone. She is the definition of above and beyond. And such a joy to communicate with! I feel so comforted knowing she was with Bandit and watching over our home.

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Stacy Arenson M.
Sitter Profile Image: Katiri S.
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Katiri S.
from
$60
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
3 years of experience
Chicago, IL, 60640

Katiri is easily the best Rover sitter we’ve ever had! She stayed with our two very high energy dogs while we were on a trip. Loved the photo and video updates and the dogs seem like they enjoyed their staycation with a new friend too. Will be booking again!

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Mikaela M.
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The median cost per night for house sitting in Uptown is $50

Pet parents share their Rover experiences - Uptown

1 / 1
5.0 out of 5 stars

Claire was so great! She stayed a few nights with my cats and sent lots of pictures and updates. I could tell my cats felt comfortable with her and I felt relieved knowing she was there!

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Colleen T.
House Sitting
5.0 out of 5 stars

Olivia has stayed with my pup twice now and she’s been a dream! Love all the updates/photos and took extra care when Augie was feeling under the weather this last time.

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Cara A.
House Sitting
5.0 out of 5 stars

Olivia took wonderful care of Boris while I was away. It was obvious when I got home that he had been happy, comfortable, and well cared for the entire time, which meant so much to me. She left my condo in excellent condition, and I really appreciated the detailed report card she put together about how Boris did throughout the stay. Her daily updates and photos were thorough and reassuring, giving me complete peace of mind while I was traveling. Knowing that Boris was content and in such good hands allowed me to fully relax and enjoy my vacation. I would highly recommend Olivia to anyone looking for a caring, reliable, and communicative pet sitter. I wouldn’t hesitate to book her again.

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Taylor B.
House Sitting
5.0 out of 5 stars

Drew was diligent, responsive, and kind. He treated our home and animals with care and respect. He is a fantastic Rover!

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Taylor C.
House Sitting
5.0 out of 5 stars

Connor took excellent care of Ivy and Elsie. He is unphased by any strange or more unique needs of dogs and you can tell he truly loves animals. He arrived promptly during the scheduled arrival time so we were able to leave for our trip on time. He followed all instructions. He is on our short list for future dog care needs whether sitting or other services.

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Katie A.
House Sitting
5.0 out of 5 stars

Melanie watched our dog, Margot, and was great! She provided tons of updates, lots of pictures and videos and spoiled our pup while we were gone. She went out of her way to do special treat games and lots of nice walks. We knew Margot was in good hands and we will absolutely use Melanie again. Highly recommend!

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Erin M.
House Sitting
5.0 out of 5 stars

Tess, yet again, was thrilled to have Jenny sit with her while we were away! Would highly recommend Jenny for all kinds of drop-in's, walking and housesitting. Tess is always excited and well looked after - and maybe spoiled a bit :)

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Jim V.
House Sitting
5.0 out of 5 stars

Brea was awesome! She was a great communicator, was punctual, displayed great attention to detail, and loves dogs. Thanks Brea!

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jenny M.
House Sitting
5.0 out of 5 stars

Julie was very communicative and professional. My cats were happy and the apartment was just as I left it.

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Marina S.
House Sitting
5.0 out of 5 stars

Tanisa was greatt with our anxious little poodle! She sent frequent updates and was very conscientious while staying at our place. We plan to work with her again in the future 🙂

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Meghan M.
House Sitting
5.0 out of 5 stars

Ryan was great! We were gone for an extended period and he took care of everything in our absence, including, most importantly, keeping our cats company and on schedule! Everything in the house was in perfect order upon our return. A great experience for our first time with Rover, and would definitely call upon Ryan in the future.

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Larry B.
House Sitting
5.0 out of 5 stars

Rahaf did an amazing job with our pups! We came home to two well cared for dogs and a well cared for home!

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Kylie R.
House Sitting
5.0 out of 5 stars

Margaret was great with Brave! We did a meet up in advance to cover the basics and she took careful note. During the stay, she was very communicative and sent me updates each day. She handled little tasks for me like retrieving Brave’s food deliveries. Margaret took him on lots of adventures around the neighborhood and made sure his brain was activated at home with food puzzles. She’s a great photographer and took really stunning photos of him each day. We will gladly work with her again!

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Kris P.
House Sitting
5.0 out of 5 stars

I cannot say enough wonderful things about Gaby! She was absolutely amazing with my Great Dane, Ella, and gave me something every dog parent hopes for when traveling: complete peace of mind. From the very beginning, Gaby was thoughtful, warm, and incredibly attentive. She took the time to come meet Ella beforehand, get to know her personality and routine, and understand our home and everything she would need while I was away. Throughout the entire time, Gaby was dependable, communicative, and consistently went above and beyond. She arrived on time, kept me updated with texts, photos, and videos, and it was so clear that Ella was happy, comfortable, and getting lots of love and attention. I felt completely at ease from day one. When my flight home was delayed, Gaby even offered to make an additional visit to ensure Ella was taken care of. That kind of thoughtfulness means everything when you’re away from a pet you love. Ella absolutely LOVES Gaby, and so do I! I feel incredibly lucky to have found someone I trust so completely with my big girl and my home. Gaby will absolutely be my first call the next time I need someone to care for Ella. Thank you so much, Gaby! Ella and I will definitely see you again soon! ❤️🐾

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Michelle T.
House Sitting
5.0 out of 5 stars

Henry agreed to take care of my dog at the last moment. He was thorough in asking for instructions and took very good care of my dog. My dog is very shy but they became friends very quickly - using him as headrest while we were gone. Thanks !!

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Pranati S.
House Sitting
5.0 out of 5 stars

Danielle is great with Brave and she is very responsive and prompt. He got plenty of exercise while I was away and he was well cared for and attended. She took on little tasks like getting his deliveries and helping me with things I needed while away. She also took great care of the home when I was gone so I came back to a clean, organized space. It was very easy to work with Danielle and we will work with her again in the future!

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Kris P.
House Sitting
5.0 out of 5 stars

Zhanna did a fantastic job taking care of Jaxy and our home while we were away!! We returned to a very happy healthy dog and a clean home. Zhanna was excellent at communicating and sending pictures to make us feel extra relaxed while we were away. 10/10 would recommend. Thank you Zhanna!

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Weston E.
House Sitting
5.0 out of 5 stars

Josh is the BEST. He took care of our two energetic dogs, a 3yo golden retriever and 2yo husky, for a week at our house. He sent regular updates that completely put us at ease and very often made us smile. It was clear from the pictures and the dogs’ demeanors when we got home that they were extremely well taken care of… loved on and exercised. Josh also must have cleaned the house, which is very thoughtful and made coming home after travels all the better. He’s awesome! Book him!

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Isabella B.
House Sitting
5.0 out of 5 stars

Always does an incredible job taking care, communicating, and leaving the house in great condition!!

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Joel H.
House Sitting
5.0 out of 5 stars

Susana was great! She took wonderful care of our young puppy and left our home in perfect condition. We will absolutely be using her again!

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Amber & Ian S.
House Sitting
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Sitters in Uptown average 4
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