41 days in Chicago Itinerary

41 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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1
Chicago
— 40 nights

40
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to South Bend (Basilica of the Sacred Heart, University of Notre Dame, & more), Whiskey Acres Distilling Co. (in DeKalb) and Janesville (Rotary Botanical Gardens & CAMDEN Playground). And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, learn more about the world around you at Field Museum, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and admire the landmark architecture of 360 Chicago Observation Deck.

Plan a trip to Chicago easily and quickly by telling Inspirock to suggest an itinerary.

If you are flying in from Jordan, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. October in Chicago sees daily highs of 21°C and lows of 11°C at night. Cap off your sightseeing on the 29th (Fri) early enough to travel back home.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Milwaukee, Saint Joseph, Evanston, Wheaton, Oak Park
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

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