Search Deals on
Chicago Vacation Packages

Build your package with 2 more options

Chicago Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Sheraton Grand Chicago Riverwalk
Hotel Riu Plaza Chicago
Level Chicago Fulton Market
Park Hyatt Chicago
LondonHouse Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile
Hotel Felix River North/Magnificent Mile

Chicago Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Sheraton Grand Chicago Riverwalk
Park Hyatt Chicago
Pendry Chicago

Chicago Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Sheraton Grand Chicago Riverwalk
Hotel Riu Plaza Chicago
Level Chicago Fulton Market

Top Flight Deals

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

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines