House Sitting In Uptown Chicago

Find a loving house sitter to watch over your pets and your home.

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Top rated Uptown house sitters

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: Neal B.
Verified Enhanced Background Check
Neal B.
Star Sitter
from
$30
per night
5.0 out of 5 stars
14 reviews
6 repeat clients
35 years of experience
Uptown, Chicago, IL, 60640

This was my first time using Rover and Neal made it a great experience! Neal took great care of my dog Titus while I was on a trip and I couldn’t be more thankful. I was gone for 2 weeks and he sent me multiple pictures and updates throughout the trip! He made sure to take Titus for walks and that he got his medicine every morning and he looked happy in every picture Neal sent and I couldn’t ask for more. I would 100% use Neal for every trip I take in the future.

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Colin V.
Sitter Profile Image: Ryan C.
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Ryan C.
Star Sitter
from
$55
per night
5.0 out of 5 stars
68 reviews
20 repeat clients
10 years of experience
Lake View, Chicago, IL, 60657

Ryan was a great house sitter for our dog during Christmas week. He was professional, friendly, and communicative. We appreciated that he shared updates and pics every day. Would definitely recommend, and will book again!

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

Renee was awesome!! Super communicative and patient. She took amazing care of our finicky dog and cat! We would absolutely book with her again!

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Laura E.
Sitter Profile Image: Tammy G.
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Tammy G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
10 reviews
7 repeat clients
5 years of experience
North Center, Chicago, IL, 60613

Tammy was a fantastic sitter for my cat Solana! She was so kind and asked all detailed questions about my cat’s medication and food schedule. I loved all the picture updates she gave of how my cat was doing while I was out of town. Thank you Tammy!

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Gabrielle B.
Sitter Profile Image: Ana D.
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Ana D.
Star Sitter
from
$40
per night
4.9 out of 5 stars
15 reviews
6 repeat clients
5 years of experience
Lincoln Park, Chicago, IL, 60614

Ana was wonderful! She was timely and very responsive. I could tell that Ollie was super comfortable with her too.

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

Emily was great to work with and really helped us out on short notice a couple of times. She was flexible, easy to coordinate with, and clearly understood what our dog needed. We felt very comfortable leaving him in her care and have already booked her again. Thank you, Emily!

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Sheryll J.
Sitter Profile Image: Liam G.
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Liam G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
50 reviews
16 repeat clients
10 years of experience
Uptown, Chicago, IL, 60640

Liam was incredible! We really appreciated his help and communication — not to mention our house was spotless when we got home! Will absolutely be using Liam again!

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Virginia F.
Sitter Profile Image: Saylor S.
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Saylor S.
from
$83
per night
5.0 out of 5 stars
62 reviews
21 repeat clients
10 years of experience
Uptown, Chicago, IL, 60640

This was the first time I've used the site so I was understandably nervous, however Jose met with me the day before my trip to get acquainted with my apartment and my pups. He took notes as he asked about my preferences for their care. Throughout the stay he sent me updates with pictures on my dogs and responded quickly whenever I reached out to him. He is very professional, personable and friendly, and my dogs bonded with him immediately. Highly recommend.

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Shawn W.
Sitter Profile Image: Christopher P.
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Christopher P.
from
$65
per night
4.8 out of 5 stars
43 reviews
19 repeat clients
10 years of experience
Uptown, Chicago, IL, 60640

Chris was so great! He stayed in our home and was great at communicating throughout the time we were away. We are watching an older family dog and he was great with her! You can tell he has a passion for pets and his presence makes anyone feel comfortable. 100% recommend.

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Julie P.
Sitter Profile Image: Gail B.
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Gail B.
Star Sitter
from
$64
per night
5.0 out of 5 stars
73 reviews
18 repeat clients
27 years of experience
Uptown, chicago, IL, 60640

We’ve used Gail for watching our Rue in our home, she is professional, punctual and I’m always happy she is able to help us!! I will continue to request her services!!

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Christina C.
Sitter Profile Image: Mikayla B.
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Mikayla B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
16 reviews
10 repeat clients
12 years of experience
Uptown, Chicago, IL, 60640

Mikayla took care of my house and cats for 2 weeks while I was out of the country on vacation. Knowing I am an anxious cat mom, she sent daily updates and pics and kept me up to speed with the local happenings, both cat and non-cat related. I returned yesterday and my cats showed no signs of having missed me, which means she did an excellent job! Great communicator and too great care of my house and cats....would definitely hire again.

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Tracy B.
Sitter Profile Image: Luisa C.
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Luisa C.
from
$69
per night
5.0 out of 5 stars
23 reviews
6 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: Nicholas B.
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Nicholas B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
18 reviews
12 repeat clients
18 years of experience
Uptown, Chicago, IL, 60640

Nicholas did a fantastic job watching our little Millie on short notice and navigating her separation anxiety. Will absolutely be booking again!

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Alan W.
Sitter Profile Image: Drew B.
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Drew B.
from
$90
per night
5.0 out of 5 stars
28 reviews
2 repeat clients
9 years of experience
Chicago, IL, 60640

Drew was prompt, responsive, and helpful with giving the dogs medication and care! He left my place clean and ready for my return. Highly recommend!

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Amanda L.
Sitter Profile Image: Duncan W.
Verified Enhanced Background Check
Duncan W.
Star Sitter
from
$60
per night
5.0 out of 5 stars
15 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: Cierra T.
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Cierra T.
from
$75
per night
5.0 out of 5 stars
20 reviews
6 repeat clients
15 years of experience
Uptown, Chicago, IL, 60613

Thanks for watching Rupert and taking care of him!

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Trevor & Iain G.
Sitter Profile Image: Andre H.
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Andre H.
from
$50
per night
5.0 out of 5 stars
73 reviews
20 repeat clients
20 years of experience
Uptown, Chicago, IL, 60640

My house was left as clean as I left it! My babies were obviously well cared for, and Andre was so kind when I wanted to check in. I wish all of my care experiences were this good. One of my babies had to take a pill, and is highly suspicious, and he got her anti-inflammatory in her!

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Fifi R.
Sitter Profile Image: Vanessa S.
Verified Enhanced Background Check
Vanessa S.
from
$45
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
10 years of experience
Lincoln Square, Chicago, IL, 60640

Absolutely no problems and very communicative. Vanessa was great with my Saint Bernard!

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Gavin C.
Sitter Profile Image: Jamie G.
Verified Enhanced Background Check
Jamie G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
53 reviews
15 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: Jasmin U.
Verified Enhanced Background Check
Jasmin U.
Star Sitter
from
$79
per night
5.0 out of 5 stars
41 reviews
15 repeat clients
6 years of experience
Uptown, Chicago, IL, 60640

Jasmin was great! I get very anxious when I leave my cat Velvet to go out of town - Jasmin sent me updates and photos and followed instructions perfectly. She was very thorough and caring when it came to information about Velvet’s care, the apartment, etc. Thanks Jasmin!

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Lisa H.
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Uptown pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Logan did great taking care of my dog. Appreciated his willingness to help me out with short notice and he left my dog very well taken care of. If you need a sitter for your dog, Logan is a great option. Thank you again!

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Jackson W.
House Sitting
5.0 out of 5 stars

Ashlee is one of our go to sitters for our dog, Geneva. She takes excellent care of our dog, and we always come back to a very happy pup!

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Allyson G.
House Sitting
5.0 out of 5 stars

Ana is so great!! She helped us out so much with Nova. She gave us so many updates and sent us wonderful photos of Nova. Nova was so happy to have her. Highly recommend for your dog sitting!

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Jyoti S.
House Sitting
5.0 out of 5 stars

Bianca took fantastic care of our dog, Chef. We received plenty of updates and photos throughout the stay, which gave us a lot of peace of mind knowing he was in such good hands. The best part was coming home to a relaxed, happy dog who was clearly well cared for and comfortable the entire time. I would absolutely recommend her to anyone looking for a dog sitter.

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Joe D.
House Sitting
5.0 out of 5 stars

Olivia was great sitting my 2 dogs overnight. She took great care of them and they loved her. She sent good updates with pictures. I came home to a clean apartment and happy pups. Thanks Olivia!

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Hilary M.
House Sitting
5.0 out of 5 stars

Wow!!! Eavan was incredible! One of the best dog sitters I’ve had by far. Not only did they take excellent care of my pitbull-mix (who is reactive and a bit of a puller on walks), they also took amazing care of my apartment while I was gone. I came back to the place looking even better than I left it, with my dog super calm and contented, which is the best after a long trip. I will definitely be rebooking for my next trip. Highly recommend Eavan!

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Emily W.
House Sitting
5.0 out of 5 stars

Sofia always takes the best care of my cat, and he feels super comfortable with her! She’s super responsive, attentive, and really great with cats.

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Dunia M.
House Sitting
5.0 out of 5 stars

Vanessa was beyond exceptional from start to finish—from communciation, to her care for my pup. She was super understanding of canela's natural shyness and temperament, which made me feel really comfortable stepping away while she was in her care. Would look to work with her every time! Thanks so much Vanessa!

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Daniella R.
House Sitting
5.0 out of 5 stars

Liam was excellent with my Galway! He communicated well and took Galway on many walks, leaving her tuckered out when she came home. Thanks for your great care!!

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Jacqueline M.
House Sitting
5.0 out of 5 stars

Megan (Gem) was an absolute delight to have with my two babes while I was on vacation. My one girl is very weary of people and Megan had such patience and before you knew it, she was very open to her. She updated me often with many pictures about how they all were doing. Always offered to help with anything that was needed at the place including grabbing packages. She now helps a neighbor and when we ran into her, they were very pleased to see her. Just more proof she became close with them. Rebooked once and will definitely again! A true Gem!

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Michelle T.
House Sitting
5.0 out of 5 stars

Sara is the best! She sent lots of updates, and I know my dog had the best time. Sara took great care of her and I would highly recommend!

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Kathryn M.
House Sitting
5.0 out of 5 stars

I cannot say enough good things about Claire. We have a reactive dog with medical needs, and Claire was absolutely amazing for her. Not only did she pay attention to our pup’s medicine schedule and reactivity training, but Claire also clearly loved our girl as her own. I cannot possibly explain how grateful we are for Claire’s care!!!!!

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Lindsey N.
House Sitting
5.0 out of 5 stars

Tony has watched my dogs a few times and always does an amazing job! They are well cared for, exercised, and he does so well with all their quirks. Very reliable and a dog sitter I will definitely hire again!

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Jesse G.
House Sitting
5.0 out of 5 stars

Olivia is awesome! She was prompt, a great communicator who often sent pics, and most importantly my dogs loved spending time with her. We highly recommend Olivia to anyone looking for a safe and reliable caregiver for your fur babies. Thanks so much Olivia —Toby and Bowie can’t wait til you come again :)

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Tina C.
House Sitting
5.0 out of 5 stars

Jack was a great sitter for our cat and dog. He took great care of them and our home for several days. When we got back our pets were happy and well loved on. We’ve already booked him for our next trip away.

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Larissa T.
House Sitting
5.0 out of 5 stars

Andre was an excellent dog sitter for my dog, Colby. From the beginning, he had great communication during the handoff of Colby’s care and kept me updated daily while I was away. It gave me so much peace of mind knowing Colby was being so well cared for. When I returned home, Colby was happy, relaxed, and clearly well looked after. Andre also left my house spotless and exactly as I had left it. I truly appreciate finding someone as reliable and caring as Andre, and I highly recommend him to anyone looking for a trustworthy dog sitter.

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Chip W.
House Sitting
5.0 out of 5 stars

Gail was fantastic! She took great care of my dog while I had to travel out of town. She was highly attentive to Bella’s schedule and routine and was respectful of my space while staying here. I would highly recommend Gail as a sitter.

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Chris W.
House Sitting
5.0 out of 5 stars

Danielle took great care of my pup, sending updates as requested and making sure she was comfortable. Highly recommend her services!

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Reece B.
House Sitting
5.0 out of 5 stars

Devon was great! Our cats were well taken care of, and it gave us great peace of mind while we were out of town. Communication was excellent as well. We would use Devon again!

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Hanah C.
House Sitting
5.0 out of 5 stars

Eleanor was reliable and took good care of my cat and my house. My cat liked her right away. Everything went well and I would book her again

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Hillery S.
House Sitting
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How Rover works

  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

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

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

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Uptown house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Uptown.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Uptown house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.