16 days in Chicago Itinerary

16 days in Chicago Itinerary

Created using Inspirock Chicago journey 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.
Explore Chicago's surroundings by going to Whiskey Acres Distilling Co. (in DeKalb), Wheaton (Cantigny Park & First Division Museum at Cantigny) and South Bend (University of Notre Dame, Grotto of Our Lady Lourdes, & more). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, wander the streets of The Magnificent Mile, see the interesting displays at The Field Museum, and explore and take pictures at Millennium Park.

To find ratings, other places to visit, where to stay, and tourist information, you can read our Chicago road trip planning tool .

If you are flying in from Saudi Arabia, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. Expect a daytime high around 32°C in June, and nighttime lows around 20°C. Cap off your sightseeing on the 16th (Sun) early enough to travel back home.

Things to do in Chicago

Museums Parks Outdoors

Side Trips

Oak Park, South Bend, Wheaton, Racine, Saint Joseph
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Wrigley Field ©
Wrigley Field

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