29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago itinerary builder

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Chicago
— 28 nights

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Chicago

— 28 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from the city and head to Little Red Schoolhouse and Prairie Wolf Slough. Visit Rosewood Beach and Whihala Beach for some beach relaxation. Change things up with these side-trips from Chicago: Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha), Swallow Cliff Stairs (in Palos Park) and Chesterton (Coffee Creek Watershed Preserve & Cowles Bog). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, engage your brain at Museum of Science and Industry, take in the spiritual surroundings of Fourth Presbyterian Church, and don't miss a visit to The Magnificent Mile.

To find traveler tips, maps, photos, and other tourist information, refer to the Chicago road trip planning site.

April in Chicago sees daily highs of 59°F and lows of 40°F at night. Wrap up your sightseeing on the 18th (Sat) to allow time to travel back home.

Things to do in Chicago

Parks · Wildlife · Outdoors · Trails

Side Trips