House Sitting Uptown

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Over 1,756
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.

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Sitter Profile Image: Vanessa S.
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Vanessa S.
from
$55
per night
5.0 out of 5 stars
31 reviews
14 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: Duncan W.
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Duncan W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
13 years of experience
Chicago, IL, 60613

Duncan was great with Teddy. He provided updates, followed all of our preferences, and we came home to a very happy puppy. He even helped by bringing up packages (which in the midst of wedding planning, was quite a few) and left the apartment better than he found it. So glad we booked Duncan and we’ll definitely do so again in the future!

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Kendall K.
Sitter Profile Image: Gail B.
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Gail B.
Star Sitter
from
$64
per night
5.0 out of 5 stars
82 reviews
22 repeat clients
27 years of experience
Uptown, chicago, IL, 60640

Gail was great! This was our first time using Rover for our elderly dog so we were nervous how Luna would do but Gail made us feel at ease sending us photos and updates daily. Would recommend Gail and we plan to have her pet sit our dog again in the future!

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Sara W.
Sitter Profile Image: Tammy G.
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Tammy G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
16 reviews
8 repeat clients
5 years of experience
Chicago, IL, 60618

Had a great experience with Tammy, who provided in-home dog-sitting for our two dogs while we were away for a couple of weeks. She was kind, professional, communicative, and took very good care of the fur babies. We returned to a tidy house and a couple of happy, healthy doggos. Will definitely ask her to sit for us again, and would recommend her to others!

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Meghann C.
Sitter Profile Image: Doris C.
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Doris C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
15 reviews
5 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: Mariah E.
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Mariah E.
from
$65
per night
5.0 out of 5 stars
107 reviews
33 repeat clients
10 years of experience
Uptown, Chicago, IL, 60613

Collin has more fun with Mariah at this point than I think he does with us 🥰 Always gives us peace of mind to know she is caring so well for him!

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Shannon D.
Sitter Profile Image: Dana W.
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Dana W.
from
$70
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
15 years of experience
Uptown, Chicago, IL, 60640

I am so glad that I decided to find a sitter to stay with my dog while we were on vacation and that we chose Dana. Dana is a laid back person which was great to put my nervous dog at ease. She was willing to do a meet and greet so that my dog could get to know her a little before we left, which was awesome. She sent me texts and pictures of my dog during my trip and I came home to a happy dog. I couldn't have asked for anything better! I will definitely be asking Dana to watch my dog for me in the future!

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

Great sitter! Drew followed all of our instructions, took wonderful care of our dog, and sent frequent updates throughout the weekend. We would definitely book again!

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Maria C.
Sitter Profile Image: Anna J.
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Anna J.
from
$65
per night
5.0 out of 5 stars
16 reviews
6 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: Hillary O.
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Hillary O.
from
$60
per night
5.0 out of 5 stars
23 reviews
8 repeat clients
25 years of experience
Edgewater, Chicago, IL, 60660

Hillary is a fantastic Rover mom. She is more than prepared, diligent, informed, and she was more curious about Winnie as an individual dog than I have ever encountered before on Rover. It made us feel really good, and was just a lovely experience at the Meet and Greet. She made us feel SO at ease leaving our home and our Winnie with her. We have already rebooked with her and she just left yesterday because she did every single thing we asked when it came to Winnie, and she was so respectful of our home. We HIGHLY recommend Hillary! Cannot say enough good things!

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Kelley J.
Sitter Profile Image: Jamie G.
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Jamie G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
66 reviews
18 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: Jayde G.
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Jayde G.
from
$65
per night
5.0 out of 5 stars
17 reviews
8 repeat clients
5 years of experience
Chicago, IL, 60640

Jayde was a lovey house sitter! She was great with our senior dog and younger pup! She was communicative and when we arrived home the dogs were excited to see us and sad to see Jayde leave. Highly recommend!

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Kimi S.
Sitter Profile Image: Kaden M.
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Kaden M.
from
$39
per night
5.0 out of 5 stars
5 reviews
1 repeat client
6 years of experience
Rogers Park, Chicago, IL, 60626

Kaden was excellent with our pups - from the meet and greet to when he left, great communication and so trustworthy. We’ll definitely use his services again!!

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Ellen F.
Sitter Profile Image: Ryan C.
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Ryan C.
Star Sitter
from
$55
per night
5.0 out of 5 stars
99 reviews
36 repeat clients
10 years of experience
Lake View, Chicago, IL, 60657

Ryan did an excellent job taking care of my little pup. He took the time to really understand what he needed from the initial meet and greet, took notes and demonstrated care and interest in my dog, and was always very communicative. While watching him, he provided daily pictures of him and my dog playing, along with progress reports and updates on how he was doing in general. Communication was always on point. Ryan’s care for my dog, Scotch, really helped me focus on my vacation knowing that Scotch was in really great hands.

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Gaston D.
Sitter Profile Image: Kathleen N.
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Kathleen N.
Star Sitter
from
$32
per night
5.0 out of 5 stars
5 reviews
5 repeat clients
24 years of experience
Lake View, Chicago, IL, 60613

Kathleen was an excellent sitter for Ivy and Elsie. She followed our instructions carefully, and was unbothered by Elsie's special needs (delayed potty training from UTIs in her puppyhood). Not only is Elsie still developing her bladder control and more likely to have accidents, she also needs wiped with medicated wipes after every potty. Kathleen was sure to do this and she also provided regular updates with photos throughout the day/evening. Both girls had a great time and we'll be sure to hire Kathleen in the future!

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Katie A.
Sitter Profile Image: Timothy L.
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Timothy L.
from
$50
per night
5.0 out of 5 stars
5 reviews
6 years of experience
Uptown, Chicago, IL, 60640

Timothy provided excellent care for my pup while I was out of town. He was very responsive and sent us updates throughout the stay. Would happily book with him again.

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John E.
Sitter Profile Image: Madeline B.
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Madeline B.
from
$36
per night
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Uptown, Chicago, IL, 60613

Madeline was great with our 7 y/o female dalmatian, Zoey. Zoey had some digestion issues while we were gone and Madeline promptly let us know and administered the necessary treatment. Looking forwatd to Madeline watching our pup again.

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Samir H.
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
27 reviews
11 repeat clients
10 years of experience
Chicago, IL, 60625

Emily was so wonderful. My Bruno was very anxious and had GI issues all week. Emily handled everything like a champ. She was attentive and responsive. She communicated frequently and sent lots of pictures. Plus more when we asked. I would ABSOLUTELY book again. In fact I already have booked again

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Claire H.
Sitter Profile Image: Mikayla B.
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Mikayla B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
29 reviews
15 repeat clients
12 years of experience
Uptown, Chicago, IL, 60640

Mikayla was great with our old man dog and two cats! We went for an extra long weekend and had Mikayla housesit, and the old man dog really appreciated not being uprooted from his home. He’s got some health issues at his age so she administered oral meds and helped him up and down the stairs as needed. She left her house tidy, and all the animals seemed well cared for when we got home. Will definitely book again for housesitting on our next trip!

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Nicole T.
Sitter Profile Image: Schyler J.
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Schyler J.
from
$50
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Uptown, Chicago, IL, 60640

Schlyer was INCREDIBLE! She seemed very knowledgeable when it came to caring for my anxious/reactive pup, asked great questions, and regularly provided updates while I was gone. I felt comfortable leaving my baby under her care, and will definitely be booking with her again for future trips.

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Ava F.
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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

Joey was professional, friendly, and very communicative! My pups got their steps in for sure too! Nothing better than coming home to happy, tired, pups :) I’d definitely recommend him to anyone looking for pet care!

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Samantha F.
House Sitting
5.0 out of 5 stars

Maeve was amazing with my dog, Millie! She sent me updates throughout my time away and made sure that Millie was well taken care of. Millie loved having her in my apartment and she left everything very clean. Maeve truly went above and beyond, I would absolutely book with her again.

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Kelsey M.
House Sitting
5.0 out of 5 stars

Great as always. My pup had a little unexpected health issue while he was with Ray and Ray notified me right away and handled it amazingly. All was well in the end, but glad he was there handle it and it went very smoothly and without drama.

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D L.
House Sitting
5.0 out of 5 stars

Great job, per usual! Kaira’s done a few overnight stays for us now, and she is one of my most trusted dog sitters, she takes great care of Chapo, my place, and provides regular updates and photos. It’s nice being able to travel worry free!

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Onya E.
House Sitting
5.0 out of 5 stars

Jack was great and really helped us out looking after Drax during our weekend away. Respectful and felt very confident we were leaving our dog in good hands. Will be a repeat customer

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Andrew M.
House Sitting
5.0 out of 5 stars

Duncan was great with Teddy. He provided updates, followed all of our preferences, and we came home to a very happy puppy. He even helped by bringing up packages (which in the midst of wedding planning, was quite a few) and left the apartment better than he found it. So glad we booked Duncan and we’ll definitely do so again in the future!

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Kendall K.
House Sitting
5.0 out of 5 stars

Maddie is absolutely wonderful. She house-sat for us while we were away and took exceptional care of our two cats during their first time away from home. We were understandably nervous, but Maddie's caring, attentive approach put us at ease immediately. She sent plenty of pictures throughout, which really helped ease our minds. What stood out most was her calm energy - you could tell our cats felt it and gravitated toward her right away. On top of caring so well for them, she left our apartment in perfect condition. She has a natural way with animals that's genuinely reassuring as a pet owner. We'd have her again in a heartbeat!!

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Saskia S.
House Sitting
5.0 out of 5 stars

Renee took great care of our cat and dog. She was very detail oriented and took great care in providing our pets the specialized care needed.

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Alyssa S.
House Sitting
5.0 out of 5 stars

Claire stayed over with our puppy and cat while we were away — she sent updates and photos, and took the time to get to know them before the stay started!

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Marley E.
House Sitting
5.0 out of 5 stars

Tzuriya was great! Our home is clean and our pets are very happy and cared for. We definitely look forward to hiring her again in the future!

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Iain G.
House Sitting
5.0 out of 5 stars

Savannah was such a wonderful house/pet sitter for our dog Annie while we were gone for a week. I would definitely recommend her to anyone and look forward to having her watch Annie again in the future! ❤️

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Gretchen B.
House Sitting
5.0 out of 5 stars

Henry is fantastic! My dog has only been with me 8 months and she is extremely anxious. Henry was. Godsend being so patient, responsive, and considerate. I felt so much better knowing he was here with her.

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Jessica C.
House Sitting
5.0 out of 5 stars

Andre is reliable, follows instructions to a T, communicative, left our house better than how he arrived, and was SOOOO wonderful with our two elderly dogs that have health issues / special needs. We rebooked him immediately! Highly recommend booking with Andre.

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Kacy A.
House Sitting
5.0 out of 5 stars

Lili was great, we felt very comfortable with our cat and dog under her care while we were out of town! She was able to safely manage our quite reactive and pully pittie, and was very communicative throughout her stay with us.

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Lizzy M.
House Sitting
5.0 out of 5 stars

Josie did not have the easiest first stay with our dog, Lewis, but she handled the hiccups well! She was also patient with our shy dog. We came home to a clean house and Josie even brought a very large package in that as delivered! We have already rebooked Josie :)

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Hannah D.
House Sitting
5.0 out of 5 stars

Sophie was wonderful! She was flexible scheduling at short notice, great communication. I came home to a very happy puppy!

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Mariana E.
House Sitting
5.0 out of 5 stars

Cece was a professional and took great care of our dogs and house. She sent multiple pictures daily and was a great communicator. Highly recommend

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Glade P.
House Sitting
5.0 out of 5 stars

Kevin was sweet and super responsive. He took great care of our babies and the apartment. Would definitely book again!

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Jordyn D.
House Sitting
5.0 out of 5 stars

Rosa was super flexible and communicative. I had to come back early as my cat wouldn’t come out of hiding for her to use the litter box or eat, and she was really understanding.

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Saira C.
House Sitting
5.0 out of 5 stars

Curtis was so friendly and communicative! My fur babies adored him and he was so kind and accommodating with my last minute scatterbrained travel plans. Seriously couldn’t have asked for a better pet and house sitter. Thanks again dude’!

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S F.
House Sitting
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Sitters in Uptown average 4
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