Chicago Itineraries

Trip Ideas for Chicago

Browse the list of day-wise Chicago itineraries and travel ideas. You can check out day by day trip plans for Chicago for 1 to 7 days. Explore how you can spend you desired number of days in Chicago with these ready-to-use itineraries.

Recent Chicago Itineraries

Looking for Chicago trip ideas? Have a look at these recently created Chicago itineraries by TripHobo users and plan your next vacation using these as templates.

What to Know Before Planning an Itinerary to Chicago

51.5% of people plan their visit to Chicago during the months of June, July and August

Most people start planning their trip to Chicago around 1 month in advance

95% of people vacationing in Chicago visit Millennium Park

76.76% of people prefer to commute by car while visiting Chicago

77.49% of people visiting Chicago are from United States

* The facts given above are based on traveler data on TripHobo and might vary from the actual figures

Be Smart! Try quickest way to plan your trip online now!

New to D.I.Y. planning? Learn how to make an itinerary on TripHobo!