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Old Town Chicago vacation rentals
We found 609 vacation rentals — enter your dates for availability
Discover a selection of 17 homes, 12 apartments, and other vacation rentals in Old Town Chicago that are perfect for your trip. Vacation rentals offer the best amenities for you and your friends, family, or even pets, like parking and a TV. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.
Find the best place to stay - Old Town Chicago
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sleeps 4 · 1 bedroom · 1 bathroom
Find spaces that suit your style
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Top rated rentals - Old Town Chicago
Photo gallery for GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Old Town stay
- 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