16 days in Chicago Itinerary

16 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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1
Chicago
— 15 nights

15
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, & more), Milwaukee (Basilica of St. Josaphat, Chudnow Museum of Yesteryear, & more) and Saint Joseph (Whirlpool Compass Fountain & Silver Beach Carousel). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, engage your brain at Museum of Science and Industry, take a leisurely stroll along Navy Pier, and make a trip to Skydeck Chicago - Willis Tower.

To see traveler tips, ratings, and tourist information, go to the Chicago day trip planning app .

If you are flying in from Canada, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In September, plan for daily highs up to 30°C, and evening lows to 19°C. Finish your sightseeing early on the 27th (Fri) to allow enough time to travel back home.

Things to do in Chicago

Museums Parks Historic Sites

Side Trips

Milwaukee, Oak Park, South Bend, Saint Joseph, Wheaton
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

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