45 days in Chicago Itinerary

45 days in Chicago Itinerary

Created using Inspirock Chicago travel route planner
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Chicago
— 43 nights
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Chicago
— 1 night

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Chicago — 43 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago Chocolate and Dessert Tour has been added to your itinerary. Discover out-of-the-way places like Chicago Riverwalk and Chicago River. Explore the numerous day-trip ideas around Chicago: South Haven (Michigan Maritime Museum, Van Buren State Park, &more), Bridgman (Warren Dunes State Park & Weko Beach Park) and South Bend (East Race Waterway, Basilica of the Sacred Heart, &more). Spend the 11th (Sun) exploring nature at Indiana Dunes National Park. There's still lots to do: explore the world behind art at The Art Institute of Chicago, walk around Millennium Park, admire the landmark architecture of Holy Name Cathedral, and laugh and play at Fox in a Box Chicago.

To see photos, more things to do, where to stay, and other tourist information, use the Chicago trip planner.

Use the Route module to find suitable travel options from your home destination to Chicago. In August, daily temperatures in Chicago can reach 83°F, while at night they dip to 67°F. On the 29th (Thu), you'll have the morning to explore before heading off to Chicago.
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Parks · Museums · Outdoors · Nature
Side Trips
Find places to stay Aug 17 — Sep 29:

Chicago — 1 night

Windy City

Start off your visit on the 29th (Thu): walk around Palmisano Park, then admire the natural beauty at Morton Arboretum, and then pause for some photo ops at Union Stockyard Gate. Get ready for a full day of sightseeing on the next day: stroll around Ping Tom Memorial Park, get engrossed in the history at Jane Addams Hull-House Museum l,ll, snap pictures at BP Pedestrian Bridge, tour the pleasant surroundings at Lakefront Trail, then admire the local landmark of Buckingham Fountain, and finally sample some tasty brews at a beer tour and tasting.

For where to stay, reviews, maps, and more tourist information, read our Chicago online holiday planner.

Wrap up your sightseeing on the 30th (Fri) to allow time to travel back home.
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Side Trip
Find places to stay Sep 29 — 30: