7 days in Chicago Itinerary

7 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

Make it your trip
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Chicago
— 6 nights

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Chicago

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Give yourself a bit of retail therapy at The Magnificent Mile and Chicago Cultural Center. Museum-lovers will appreciate The Art Institute of Chicago and Cantigny Park. Change things up with these side-trips from Chicago: Little Red Schoolhouse (in Willow Springs) and Rosewood Beach (in Highland Park). There's lots more to do: get a taste of the local shopping with Ernest Hemingway Birthplace, admire the landmark architecture of Frank Lloyd Wright Home and Studio, steep yourself in history at Frank Lloyd Wright's Robie House, and walk around Millennium Park.

To see photos, ratings, and other tourist information, you can read our Chicago road trip tool.

In June, plan for daily highs up to 81°F, and evening lows to 63°F.

Things to do in Chicago

Museums · Parks · Historic Sites · Outdoors

Side Trips

Find places to stay Jun 19 — 25: