Chicago trip planner
Create a fully customized day-by-day itinerary for free
Chicago
Windy City
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants. Renowned for its distinct architecture that provides countless sightseeing opportunities, the city attracts tourists with its cosmopolitan atmosphere and genuine friendliness, charming visitors with a sense of hospitality rarely found in other urban centers its size. The hub of the Midwest, Chicago features a picturesque skyline set against the waters of Lake Michigan, resembling more an inland sea than a freshwater lake. You have plenty to choose from for a diverse itinerary, including visits to the city's lakefront, huge parks, public squares, and world-class museums of art and science. With the Inspirock world travel planner, Chicago and other destinations across the globe can be made central to your personalized travel plans.
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Top Chicago tours
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Side trips from Chicago
Museums in Chicago
Hidden gems in Chicago
Historic Sites in Chicago
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Places to visit with Chicago
SpringfieldTrip planner
Best for: History Museum, Historic Site, Landmark
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Best for: Distillery, Historic Site, Nightlife
Oak ParkTrip planner
Best for: Architectural Building, Historic Site, Religious Site
RockfordTrip planner
Best for: Garden, Children’s Museum, Water Park
EvanstonTrip planner
Best for: Room Escape Game, Theater, History Museum
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