Cheap Holidays to Chicago

Choose two or more items and save on your trip:

Top deals for trips to Chicago

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Level Chicago – Old Town
Hotel Riu Plaza Chicago
Ruby Room
Waldorf Astoria Chicago

Chicago Holiday Packages for 4 Nights

Price found within the past 48 hours. Click for updated prices.
The Westin Chicago Lombard
Wyndham Chicago O'Hare
DoubleTree by Hilton Chicago - North Shore Conference Center
Wyndham Garden Elk Grove Village/O'Hare
Hilton Garden Inn Chicago OHare Airport

Chicago Holiday Packages for 6-7 Nights

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Level Chicago – Old Town
Hotel Riu Plaza Chicago
Ruby Room
Waldorf Astoria Chicago

Best Chicago hotel deals for your holiday

Don't see what you're looking for?
See all available properties in Chicago
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cheap flights to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on ebookers.ch from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.