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Destinations overview -> USA -> Chicago

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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

Highlights Of Route 66 And Albuquerque Balloon Fiesta
16 nights starting at $4,309.00
from Cosmos
available 10/3/2025 - 10/19/2025
Mackinac Island & The Great Lakes
7 nights starting at $3,299.00
from Globus
available 6/8/2025 - 6/15/2025
Cruising the Great Lakes: Toronto to Chicago - Westbound
11 nights starting at $10,790.00
from Tauck
available 8/18/2025 - 8/29/2025

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