Downtown Chicago vacation rentals
We found 776 vacation rentals — enter your dates for availability
Find the perfect place for your stay in Downtown Chicago by choosing from 259 houses, 52 condos, and other vacation rentals. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include air conditioning and a pool. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.
Find spaces that suit your style
House
Condo/Apartment
Find properties near top attractions in Downtown Chicago
Map Attractions
Find the best place to stay - Downtown Chicago
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sleeps 4 · 1 bedroom · 1 bathroom
Top rated rentals - Downtown Chicago
Photo gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Wonderful place!
- 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