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Old Town Chicago vacation rentals
We found 606 vacation rentals — enter your dates for availability
Discover a selection of 14 homes, 19 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
Houses
Top rated rentals - Old Town Chicago
Photo gallery for Luxury House in the heart of Old Town with Parking
Five-Star Luxury, Comfy Beds, and Skyline Views Await at this Old Towne Gem!
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value