Chicago Trips

Browse our hand-picked trip ideas for the Chicago area or share your list of best things to do.
  • There are many sights around Chicago that served as gangster hot spots. Explore the famous mafia spots whether on a guided tour or on your own.
  • Searching for a great Irish atmosphere in Chicago. Here is a list of some of the most popular spots.
  • Chicago's theatre district offers great shows and play in all price ranges.
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EDIT THIS ITINERARY Our list of trips in Chicago uses some content from Wikipedia and Wikivoyage.