20 days in Chicago Itinerary

20 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

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1
Chicago
— 19 nights

19
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your inner history buff will appreciate Millennium Park and Riverwalk Lot. You'll explore the less-touristy side of things at Starved Rock State Park and Midewin National Tallgrass Prairie. Venture out of the city with trips to Utica (August Hill Winery Tasting Room & Matthiessen State Park), Sarett Nature Center (in Benton Harbor) and Grand Mere State Park (in Stevensville). The adventure continues: kick back and relax at Silver Beach County Park, try to win big at Horseshoe Hammond Casino, identify plant and animal life at Fernwood Botanical Garden and Nature Preserve, and engage your brain at Museum of Science and Industry, Chicago.

To see reviews, photos, traveler tips, and more tourist information, you can read our Chicago trip planning website .

If you are flying in from Nigeria, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In December, daily temperatures in Chicago can reach 4°C, while at night they dip to -2°C. Finish your sightseeing early on the 14th (Sun) so you can travel back home.

Things to do in Chicago

Parks Outdoors Wildlife

Side Trips

Utica, Lake Geneva, Coloma, South Bend, Michigan City
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Silver Beach County Park ©
Silver Beach County Park
Starved Rock State Park ©
Starved Rock State Park

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