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3 days · Chicago itinerary

Chicago in 3 Days: The Complete Itinerary

Three days in Chicago cover the skyline, the museums and the food. Here is how to spend three perfect days — with the best-rated tours to book.

At a glance

  1. 1Day 1: river & skyline
  2. 2Day 2: museums
  3. 3Day 3: food & history
  4. 4Lakefront

Day 1: the skyline

Architecture cruise and observation decks.

Day 2: culture

The Art Institute and museums.

Day 3: food & history

A food tour and gangster history.

Chicago in 3 days — FAQ

Is 3 days enough for Chicago?
Three days is ideal — the skyline and cruise on day one, museums on day two, and food and history on day three.
What are the best things to do in Chicago in 3 days?
The architecture cruise, observation decks, the Art Institute, a food tour and a gangster history tour are the highlights.
How do I plan a 3-day Chicago itinerary?
Spend day one on the skyline and cruise, day two on museums, and day three on food and history tours.