30 days in Chicago Itinerary

30 days in Chicago Itinerary

Created using Inspirock Chicago travel route builder

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Chicago
— 29 nights

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Chicago

— 29 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your inner history buff will appreciate Cantigny Park and Fourth Presbyterian Church. You'll explore and learn at The Art Institute of Chicago and Ernest Hemingway Birthplace. Explore Chicago's surroundings by going to Milwaukee (Basilica of St. Josaphat, Pabst Mansion, &more), South Bend (Basilica of the Sacred Heart & Grotto of Our Lady Lourdes) and Baha'i House of Worship (in Wilmette). There's still lots to do: steep yourself in history at Frank Lloyd Wright's Robie House, enjoy the sea views from South Haven Lighthouses, engage your brain at Field Museum, and get to know the fascinating history of Chicago Riverwalk.

To see ratings, more things to do, reviews, and more tourist information, you can read our Chicago road trip planner.

Expect a daytime high around 83°F in August, and nighttime lows around 67°F. Wrap up your sightseeing on the 22nd (Sun) to allow time to travel back home.

Things to do in Chicago

Historic Sites · Museums · Parks · Shopping

Side Trips