8 days in Chicago Itinerary

8 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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Chicago
— 7 nights

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Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Boat Tours & Water Sports and Prairie Wolf Slough. The Art Institute of Chicago and The Magnificent Mile are good opportunities to explore the local culture. Get out of town with these interesting Chicago side-trips: Cowles Bog (in Chesterton), South Bend (Basilica of the Sacred Heart & Grotto of Our Lady Lourdes) and Little Red Schoolhouse (in Willow Springs). Next up on the itinerary: contemplate the long history of Ernest Hemingway Birthplace, get curious at Field Museum, trek along Oak Savannah Trail, and grab your bike and head to Busse Woods Trail System.

For other places to visit, traveler tips, ratings, and more tourist information, refer to the Chicago day trip planning app.

If you are flying in from United Kingdom, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In May in Chicago, expect temperatures between 25°C during the day and 13°C at night.

Things to do in Chicago

Parks · Outdoors · Trails · Historic Sites

Side Trips

Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

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