21 days in Chicago Itinerary

21 days in Chicago Itinerary

Created using Inspirock Chicago travel route planner

Make it your trip
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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.
Venture out of the city with trips to South Bend (Basilica of the Sacred Heart & Grotto of Our Lady Lourdes), Chicago Botanic Garden (in Glencoe) and Willow Springs (Little Red Schoolhouse & Centennial Bike Trail). Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, stroll through Millennium Park, get curious at Museum of Science and Industry, and observe the fascinating underwater world at Shedd Aquarium.

To find traveler tips, maps, other places to visit, and tourist information, read our Chicago road trip planning site.

In February, daytime highs in Chicago are 36°F, while nighttime lows are 20°F. Finish up your sightseeing early on the 29th (Sat) so you can travel back home.

Things to do in Chicago

Museums · Parks · Historic Sites · Outdoors

Side Trips