Discover your favorite property type

House in fall colors

235 Houses

Apartment living room

802 Apartments

A hotel pool courtyard

1 Hotel

Breakfast on a balcony

2 B&Bs

Chicago Vacation Rentals

Choose from over 1,069 amazing properties in Chicago that can fit your every need. BookandStay analyzes every property to ensure it meets our high standards, saving you from spending time and money on low quality Chicago listings. Of the 1,069 premium properties in Chicago, 75% are Apartments. In case you're looking for something different there are many other types of rentals available, such as Houses and Bed and Breakfasts, the next most popular properties in Chicago. BookandStay sources our properties from top rated rental websites like HomeAway,, Vrbo (Vacation Rentals By Owner), and more.

Popular Chicago Amenities
  • 86 rentals with a Pool
  • 872 rentals with Internet
  • 864 rentals with TV
  • 185 rentals with a Fireplace
  • 867 rentals with Air Conditioning
  • 54 rentals with a Hot Tub
  • 540 rentals with Parking
  • 780 rentals with Laundry
  • 614 rentals with a Kitchen