21 days in Chicago Itinerary

Created using Inspirock Chicago tour itinerary planner
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Chicago
— 20 nights

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Chicago — 20 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to Alter Brewing Company (in Downers Grove), South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, &more) and Morton Arboretum (in Lisle). The adventure continues: admire the masterpieces at The Art Institute of Chicago, get a new perspective on nature at Field Museum, take in panoramic vistas at Skydeck Chicago - Willis Tower, and admire the landmark architecture of Frank Lloyd Wright's Robie House.

For traveler tips and tourist information, you can read our Chicago road trip planning site.

If you are flying in from Canada, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. Expect a daytime high around 8°C in March, and nighttime lows around -1°C.
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Museums · Parks · Historic Sites · Breweries & Distilleries
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