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Old Town Chicago vacation rentals
We found 578 vacation rentals — enter your dates for availability
Discover a selection of 17 homes, 15 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 spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Old Town Chicago
A home away from home! <No events allowed>
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.8 out of 10
exceptional
(94 reviews)
Top rated rentals - Old Town Chicago
Amazing place and great hosts!
10 out of 10
exceptional
(182 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