Chicago trip planner
Create a fully customized day-by-day itinerary for free
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.
Create a full itinerary — for free!
Plan your trip to Chicago
- Get a personalized tripA full day by day itinerary based on your preferences
- Customize itRefine your trip. We'll find the
best routes and schedules
- Manage itEverything in one place. Everyone on the same page.
Popular things to do in Chicago
Side trips from Chicago
Museums in Chicago
Hidden gems in Chicago
Historic Sites in Chicago
Shopping in Chicago
Places to visit with Chicago
SpringfieldTrip planner Best for: History Museum, Historic Site, Landmark GalenaTrip planner 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
Recently planned trips to Chicago
3 days in Chicago BY A USER FROM UNITED STATES Chicago 10 days in Grand Canyon National Park, Yellowstone National Park & Midwest BY A USER FROM UNITED STATES Grand Canyon National Park Yellowstone National Park Chicago 5 days in Chicago & Toronto BY A USER FROM UNITED STATES Chicago Toronto 1 day in Chicago BY A USER FROM UNITED STATES Museum of Science and Industry Millennium Park Reliance Building 10 days in Chicago BY A USER FROM INDONESIA Field Museum The Art Institute of Chicago Reliance Building 5 days in Chicago BY A USER FROM UNITED KINGDOM Horseshoe Hammond Museum of Science and Industry Marquette Building