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

Architecture cruise and observation decks.

The Art Institute and museums.

A food tour and gangster history.

Top-rated tours for exactly what this plan recommends in Chicago — prices per person.

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.