56 days in Chicago Itinerary

56 days in Chicago Itinerary

Created using Inspirock Chicago tour itinerary builder

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Chicago
— 55 nights
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Chicago

— 55 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore hidden gems such as Chicago Riverwalk and Chicago Skyline. Get out of town with these interesting Chicago side-trips: Caterpillar Global Mining Visitor Center (in South Milwaukee), Racine (Wind Point Lighthouse & SC Johnson Headquarters) and Southport Light Station Museum (in Kenosha). Spend the 9th (Tue) exploring nature at Indiana Dunes National Park. The adventure continues: explore the landscape on two wheels at Lakefront Trail, make a trip to Skydeck Chicago - Willis Tower, walk around Millennium Park, and explore the activities along Chicago River.

To find photos and other tourist information, go to the Chicago trip planner.

If you are flying in from Australia, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In October, plan for daily highs up to 21°C, and evening lows to 11°C. Cap off your sightseeing on the 25th (Thu) early enough to travel back home.

Things to do in Chicago

Parks · Museums · Historic Sites · Neighborhoods

Side Trips