6,774
trips planned by users
trips planned by users
Chicago trip planner
Create a fully customized day by day
itinerary for free
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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Places to visit with Chicago
SpringfieldTrip planner
Best for: History Museum, Landmark, Government Building
Oak ParkTrip planner
Best for: Architectural Building, Religious Site, Historic Site
GalenaTrip planner
Best for: Distillery, Historic Site, Nightlife
EvanstonTrip planner
Best for: Room Escape Game, Theater, History Museum
RockfordTrip planner
Best for: Garden, Children’s Museum, Water Park
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