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2 Day Chicago Itinerary

2 Day Chicago Itinerary

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This Chicago itinerary outlines every detail you need to enjoy 2 days exploring the city of Chicago. It includes 14-pages of expert advice to help you navigate your Chicago trip and maximize your experience. This guide includes recommendations to make the most out of two days in Chicago. In this itinerary you'll find recommended activities, areas to visit and restaurants in the heart of the city.

Last Updated: December 2023

Before you take this trip, listen to our  Chicago podcast episode!

Where the Chicago Travel Guide Itinerary Goes:

This comprehensive 2 day guide has you sight seeing & touring your way through Chicago. This guide can be used as a guide even if your trip is not 2 days. It is good for both tourists as well as locals looking to explore in their own backyard. This Chicago Itinerary will take you to:

  • Chicago Riverwalk
  • Navy Pier
  • Millenium Park
  • Lake Michigan
  • Willis Tower
  • Wrigleyville
  • The Signature Lounge or Cloudbar

How this Itinerary will help you

This itinerary will help you plan your day perfectly to see the best highlights of Chicago in just one day, ideal for day trippers, those visiting for a short time, or locals exploring their own backyard. It includes the hours and best time of year for the recommended things to see and do in Chicago, exact location of each attraction, estimated length of time to spend there, and distance and drive time between locations + the best places to eat in Chicago.

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