Uptown vacation rentals
We found 2,083 vacation rentals — enter your dates for availability
Discover a selection of 8 homes and other vacation rentals in Uptown that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the amenities you expect and more, which might include parking and a hot tub. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.
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Find the best place to stay - Uptown
Photo gallery for Uptown studio apartment with breathing views
![Image of Uptown studio apartment with breathing views](https://images.trvl-media.com/lodging/88000000/87740000/87736400/87736374/e94f1c9b.jpg?impolicy=resizecrop&rw=455&ra=fit)
Uptown studio apartment with breathing views
Sleeps 4 · 1 bedroom · 1 bathroom
10 out of 10
exceptional
(15 reviews)
Top rated rentals - Uptown
Photo gallery for Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway by RedAwning
![You'll love stretching out and relaxing in this sun-drenched living room](https://images.trvl-media.com/lodging/89000000/88910000/88902600/88902510/70f85fea.jpg?impolicy=resizecrop&rw=455&ra=fit)
Attractive place
10 out of 10
exceptional
(13 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value