Destinations overview -> USA -> Chicago

The Windy City offers some of the best year-round art, food, culture, and activities in the world. Check out Broadway in Chicago to see what's playing at the over 200 theaters when you visit. See one of the great sporting events. Take an architecture cruise on the historic Chicago River. Drive down Lakeshore Drive or bike or walk along Lake Shore Trail to see Grant Park, Millenium Park, Lincoln Park and Soldier Field, or to just watch the thousands of people who visit the shore of Lake Michigan each summer.

Great Trips

Waldorf Astoria Chicago main exterior
Waldorf Astoria Chicago
5 nights starting at $1,748.00
from Journese
available 12/5/2021 - 12/15/2021
product image
Discover the Great Lakes + St. Lawrence
13 nights starting at $5,799.00
from Alexander+Roberts
available 8/25/2022 - 9/7/2022
product image
Cruising the Great Lakes: Toronto to Chicago - Westbound
11 nights starting at $8,990.00
from Tauck
available 10/6/2022 - 10/17/2022

Find a Trip

Detailed Search