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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Plan your trip to Chicago
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Compose it!Your own itinerary for your car vacation, beach vacation, city trip, any near or distant journey ... ready within 10 minutes.
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Customize it.Refine your plan. We find the best routes and opportunities.
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Book it.Choose from the best accommodations (Expedia, AirBnB), airlines and activities, by yourself or share with travel professionals for the utmost experience. Up to 50% discount!
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Do it yourself.Or share your plan with travel professionals for a customized trip
Top Chicago tours
Popular things to do in Chicago
Hidden gems in Chicago
Side trips from Chicago
Museums in Chicago
Historic Sites in Chicago
Shopping in Chicago
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