5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

Make it your trip
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Chicago
— 4 nights

S M T W T F S
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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll discover tucked-away gems like Geneva Lake and Fox in a Box Chicago. Step out of Chicago to go to Milwaukee and see Milwaukee Art Museum, which is approximately 1h 35 min away. There's much more to do: don't miss a visit to Chicago Skyline, wander the streets of The Loop, admire the local landmark of Buckingham Fountain, and explore the activities along Chicago River.

Plan my trip to Chicago with suggested itineraries provided by Inspirock.

In April, daytime highs in Chicago are 59°F, while nighttime lows are 40°F.

Things to do in Chicago

Parks · Nature · Museums · Historic Sites

Side Trips