House Sitting Uptown

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Over 1,681
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: 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 took great care of our little Nugget and we are so very grateful. Our dog can be very particular, stubborn and has a particular set of care needs - most of which are typical of small terriers, but does require a caretaker/owner with patience and good attention detail. Gail took all of that on with ease -she was communicative and had a positive atttude which we really appreciate. She asked great questions and worked with us to problem solve when Nugget was not cooperating. It felt really good to leave our pet in her care and looking forward to having her look after our dog in the future!”

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Deena S.
Sitter Profile Image: Jamie G.
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Jamie G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 69 reviews
18 repeat clients
32 years of experience
Uptown, chicago, IL, 60640

“Jamie was very responsive and had great communication! He was patient with my nervous dog and took time to let him warm up. He left the house clean and in good condition and we will be happy to have him back!”

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Cameron
Sitter Profile Image: Angelique H.
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Angelique H.
Star Sitter
from
$36
per night
5.0 out of 5 stars
• 56 reviews
23 repeat clients
8 years of experience
Uptown, Chicago, IL, 60613

“Angelique did a great job house sitting for us. We have an anxious pup and we’re worried about leaving him with a stranger for the first time, but Angelique did a great job putting him at ease and he warmed up to her in no time. We would happily book with her again!”

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Aedan P.
Sitter Profile Image: Maeve H.
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Maeve H.
from
$50
per night
5.0 out of 5 stars
• 37 reviews
19 repeat clients
14 years of experience
Uptown, Chicago, IL, 60640

“Maeve was great! My dogs loved her right away and I was very comfortable leaving her with them! She sent updates and photos everyday and left our apartment even better than we did. Will definitely book again in the future!”

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Katie K.
Sitter Profile Image: Dana W.
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Dana W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 25 reviews
9 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: Megan B.
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Megan B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 20 reviews
7 repeat clients
15 years of experience
Lake View, Chicago, IL, 60613

“Megan did a great job w/ our baby! She was very attentive and took her on plenty of long walks beyond just our neighborhood. She also did a great job watching our home and handling a few tasks! Would for sure book again!”

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Andrew C.
Sitter Profile Image: Sarah E.
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Sarah E.
from
$66
per night
5.0 out of 5 stars
• 21 reviews
5 repeat clients
10 years of experience
Chicago, IL, 60640

“Sarah was easy to communicate with and very responsive! She took great care of our little chihuahua, ensuring she felt comfortable in the space and with her new dog sitter. Sandy gave Sarah lots of kisses and love when we picked her up - she didn’t want to leave! Sarah sent us lots of photos and updates while she was sitting, and it looked like they had a lot of fun together. Fantastic sitter, I will book with Sarah again!”

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Amanda & Steve Z.
Sitter Profile Image: Ryan C.
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Ryan C.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 109 reviews
38 repeat clients
10 years of experience
Lake View, Chicago, IL, 60657

“We have used Ryan’s services for walking our dogs and staying in our home and caring for them. He is fantastic!! Can’t say enough nice things about him. His communication was excellent and he would share photos of our pets. Highly recommend him.”

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Patrick Z.
Sitter Profile Image: Mikayla B.
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Mikayla B.
from
$60
per night
5.0 out of 5 stars
• 30 reviews
16 repeat clients
12 years of experience
Uptown, Chicago, IL, 60640

“Mikayla was a fantastic sitter for our senior dog over the holidays! She was super communicative and kind. Our dog was so calm and happy when we got home, traveling can be hard on her so we really appreciated having someone at our place. She also took good care of our space and everything was just as we left it and super tidy. I would highly recommend Mikayla for her pet sitting needs!”

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Jenny O.
Sitter Profile Image: Sky S.
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Sky S.
from
$45
per night
4.7 out of 5 stars
• 26 reviews
3 repeat clients
18 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: Duncan W.
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Duncan W.
Star Sitter
from
$68
per night
5.0 out of 5 stars
• 25 reviews
8 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: Timothy L.
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Timothy L.
from
$50
per night
5.0 out of 5 stars
• 6 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: Jayde G.
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Jayde G.
from
$45
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: Dylan M.
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Dylan M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 22 reviews
7 repeat clients
1 year of experience
Chicago, IL, 60657

“Dylan was a lifesaver when we had another cancellation at the last minute. He was professional and great with our senior pup. We'd definitely work with him again.”

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Krysta M.
Sitter Profile Image: Dana S.
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Dana S.
from
$65
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
15 years of experience
Lake View, Chicago, IL, 60613

About: I spent 15 years as the primary caregiver for my pit bull, from training her as a puppy at 5 months old through her senior years, learning her routines and moods inside and out and adapting her care as she aged, including managing mobility changes and medication in her later years. For the past few months I've also been pet sitting for other dogs, giving me a feel for adjusting to different personalities, routines, and households. I know what it takes to make a dog feel safe, comfortable, and loved, whether that's a high-energy pup who needs structure or an older dog who needs a gentler pace and extra patience. I bring the same attentiveness, reliability, and genuine care to every dog I look after that I gave my own for 15 years. I'm currently job searching, which gives me a flexible schedule for drop-in visits throughout the day and week. I can typically be available on short notice for quick check-ins, whether that's a midday visit, feeding, or just stopping by to give your dog some attention and a bathroom break. I'm happy to swing by multiple times a day if needed to keep your pup comfortable while you're away. For drop-in visits, I focus on keeping things calm and consistent with your dog's normal routine. I'll follow whatever instructions you leave for feeding, medication, or playtime, and I always do a quick check of food, water, and the yard or living space before I leave. I'm attentive to your dog's body language so I can tell if something feels off, and I always lock up and leave things exactly as I found them.

Sitter Profile Image: Alice E.
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Alice E.
Star Sitter
from
$68
per night
5.0 out of 5 stars
• 12 reviews
2 repeat clients
10 years of experience
Chicago, IL, 60657

“Alice watched my Australian Shepherd while I was out of town for 4 days. She gave me updates throughout the visit. I would book her again. She was easy to arrange a visit with and my dog seemed happy after.”

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Katrina K.
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

“We had an amazing experience with our Rover sitter watching our 3 kitties while we were away. She was incredibly attentive, kept us updated regularly with messages and photos, and really helped ease our anxiety about being away from home. Our cats were well cared for, and we came home to a clean and well maintained place, which we truly appreciated after traveling. You can tell she genuinely cares about the pets she watches and goes above and beyond to make both the animals and owners feel comfortable. We would absolutely book with her again and she will definitely be our go to sitter moving forward. Highly recommend!”

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Jae L.
Sitter Profile Image: Sophia B.
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Sophia B.
from
$45
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
15 years of experience
North Center, Chicago, IL, 60613

About: I’ve had dogs in the family since I was little. With both parents working it was up to my sister and I to take care of them. I’ve had experience with reactive dogs as I’ve had two pitbulls that were unfortunately poorly socialized, and I know how important it is to keep a tight leash. That doesn’t mean I love them any less :) Currently my daily life has no set schedule, this means I can help out whenever! Pet care is a priority so I will be putting that ahead of any plans that arise. I always follow their routine to keep them as comfortable as possible. I know boredom can be a big problem especially with hyper breeds, so I always give the time to keep them entertained and engaged. Bathroom breaks and walks are consistent to keep them on a schedule.

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: Rachel S.
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Rachel S.
from
$75
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
5 years of experience
Lake View, Chicago, IL, 60613

“I can’t say enough good things about Rachel! She house sat and watched my cat and dog for two weeks while I was out of the country. Being abroad can make you worry, but Rachel kept me completely at ease with her excellent communication. She sent regular photo updates and notes that showed how much she genuinely cared for my pets. Both my dog and cat absolutely loved her. She is responsible, deeply caring, and a total professional. I will definitely be hiring her again!”

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Emmi B.
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The median cost per night for house sitting in Uptown is $50

Pet parents share their Rover experiences - Uptown

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5.0 out of 5 stars

Sophia was wonderful with my chocolate lab!! I knew from our initial meet and greet that she was an animal lover, gentle and patient. Sophia was communicative and kind. Kaia loved her. I will most certainly be booking Sophia again!

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Stevi G.
House Sitting
5.0 out of 5 stars

Rachel did a fantastic job looking after my dog! She sent frequent updates with photos and info about my dog's walks and whether or not she was eating. Will absolutely be booking with her again in the future!

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Shannon C.
House Sitting
5.0 out of 5 stars

Lauren took on taking care of my dogs Sparta and Chi late notice and did a phenominal job with an in home stay. Sparta in particular can be a handful and I was thankful for the work she did with him. The apartment was in exceptional order when I returned. Would definitely hire her again!

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Peter G.
House Sitting
5.0 out of 5 stars

Carly was wonderful with our dogs and quickly earned their trust, handled challenges calmly, and kept us updated with photo updates throughout her time with them. We felt confident leaving our dogs in her care and would highly recommend her to anyone considering hiring her

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Dacia H.
House Sitting
5.0 out of 5 stars

Ellis was fantastic, I can't recommend them enough. Two of our cats are pretty shy and scared of new people, but they immediately warmed up to Ellis. They sent us daily photos to keep us updated, and all the cats were calm when we came back, which is always a great indication they got a lot of playtime and attention.

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Asaf B.
House Sitting
5.0 out of 5 stars

Jamie stayed at my place for a long weekend to watch my dog and everything went great! He sent pictures each day with an update — just enough to give context without overwhelm. Very friendly and responsive.

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Ryan B.
House Sitting
5.0 out of 5 stars

Mads took great care of Linguine and sent photo updates every day! Linguine is super high energy and Mads gave him all the attention and exercise he needed while I was out of town for a week. I would highly recommend them for excellent pet care!

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MJ J.
House Sitting
5.0 out of 5 stars

Tanisa is so lovely and our dogs and cat adored her! She took great care of our home, sent pictures and videos daily and we could tell they weren't stressed once we came home. We feel so lucky to find someone we trust and someone the gang loved!

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Bri B.
House Sitting
5.0 out of 5 stars

It was my first time leaving Roxie home with a pet sitter and Brynn really took the time and energy to make sure she had all the information possible. She really put me at ease and it allowed me to really enjoy my trip. She kept me updated multiple times a day with frame worthy photos. Thank you so much for taking such great care of my senior!

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Jasmine J.
House Sitting
5.0 out of 5 stars

Ryan was reliable, a good communicator, and took good care of my cat. I would definitely hire him again.

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Hillery S.
House Sitting
5.0 out of 5 stars

Simone was amazing! Very responsive, took great care of Winnie and the apartment, and got frequent updates/pictures while we were away. Would highly recommend!

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Parker J.
House Sitting
5.0 out of 5 stars

Alanoud came to our house to help one busy evening for a few hours. It happened to be pouring rain, but she took care of our big, rambunctious pup in good cheer nonetheless. I'm feeling quite confident about having her stay at our home for a few days while we attend a wedding out of town later this month.

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Christina R.
House Sitting
5.0 out of 5 stars

Rachel did a great job sitting my dog! She was professional and easy to communicate with - followed all care instructions - sent updates with pictures & videos - asked questions when she had them - and left my house just how i'd left it. I felt very comfortable that my dog was being cared for and would be happy to book with Rachel again.

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Alex N.
House Sitting
5.0 out of 5 stars

We love having Nicole watch our pets, and our pets love Nicole!! I have never felt so at ease leaving my pets with someone before her, she makes traveling such a breeze. Cannot recommend her enough!

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Amy C.
House Sitting
5.0 out of 5 stars

Vanessa took such great care of our pup Nellie! She sent updates frequently and was very attentive to our pup! Would highly recommend!

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Chloe D.
House Sitting
5.0 out of 5 stars

Alexandria was very communicative throughout the weekend watching 4 pets. She provided detailed notes and photo updates, which I appreciated. She went above and beyond with her care and following instructions. I felt at ease with her taking care of my pets and would highly recommend Alexandria. Will be booking for future needs!

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Ryan S.
House Sitting
5.0 out of 5 stars

Great communication and picture updates. Byran’s flexibility was much appreciated as I had travel changes and he clearly cared about Maya’s well-being.

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Jake R.
House Sitting
5.0 out of 5 stars

Hillary was the perfect sitter for us! She was very attentive to our daily schedule with our dog, and was very understanding in how we like to care for her. She followed all of our routines, and gave our dog so much love and care while we were away. She sent so many great updates and lots of photos which we appreciated. It gave us such piece of mind knowing all the things that went on while we were away. Once we arrived home, we could tell how much our dog loved Hillary. From the tail wags, zoomies, and constant pets 😊 We would recommend Hillary to anyone who wants their dog cared for by someone who treats them like their own!

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Megan B.
House Sitting
5.0 out of 5 stars

Ryan was absolutely Amazing!!! 🤩 Aidan our Welsh Terrier loved him!! He took care of him in our home. Ryan took Aidan on many walks including a long walk which was so great! Ryan’s Communications were excellent!! I highly recommend Ryan!!

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Dan G.
House Sitting
5.0 out of 5 stars

My dog loved Adam! Adam was great at sending pics, getting my dog lots of exercise, following my instructions, and asking good questions to ensure he was prepared. I will definitely book Adam again.

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Brendan G.
House Sitting
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