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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

Niagara & Great Lakes Treasures
16 nights starting at $14,590.00
from Viking Expeditions
available 5/8/2026 - 5/24/2026
Cruising the Great Lakes: Chicago to Toronto - Eastbound
11 nights starting at $10,790.00
from Tauck
available 8/25/2025 - 9/5/2025
Mackinac Island
8 nights starting at $3,299.00
from Collette
available 10/4/2024 - 10/12/2024

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