Uptown vacation rentals
We found 2,023 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
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sleeps 4 · 1 bedroom · 1 bathroom
Top rated rentals - Uptown
Photo gallery for Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Amazing Home Base Centrally Located in Chicago
- 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