52 days in Chicago Itinerary

52 days in Chicago Itinerary

Created using Inspirock Chicago itinerary planner

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Chicago
— 51 nights

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Chicago

— 51 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Buckingham Fountain and Crown Fountain. Explore the numerous day-trip ideas around Chicago: Michigan City (Shoreline Brewery & Washington Park Zoo), Chesterton (Cowles Bog, Indiana Dunes State Park, &more) and Utica (Matthiessen State Park & Starved Rock State Park). Spend the 1st (Tue) exploring nature at Indiana Dunes National Park. There's still lots to do: contemplate the waterfront views at Chicago River, find something for the whole family at Silver Beach Carousel, take in panoramic vistas at Skydeck Chicago - Willis Tower, and grab your bike and head to Lakefront Trail.

To find maps, more things to do, photos, and more tourist information, you can read our Chicago travel itinerary planner.

In July, plan for daily highs up to 83°F, and evening lows to 67°F. Wrap up your sightseeing on the 5th (Sat) to allow time to travel back home.

Things to do in Chicago

Parks · Outdoors · Museums · Beaches

Side Trips