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Home/Destinations/Chicago/Chicago in 3 days
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.

Book the experiences in this itinerary

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

Chicago Architecture Walking Tour: What's New
Chicago
Chicago Architecture Walking Tour: What's New
5.0(91)·1h 30min
from$35/ person
via Viator
#1 Rated NYC Chinatown Food and History Walking Tour with FNYT
New York City
#1 Rated NYC Chinatown Food and History Walking Tour with FNYT
5.0(193)·3 hours
from$99/ person
via Viator
Chicago Architecture and True Crime: Halloween Edition
Chicago
Chicago Architecture and True Crime: Halloween Edition
5.0(666)·1h 30min–1h 45min
from$35/ person
via Viator
Hungry Osaka Street Food Tour : 15 Tastings, 4 Drinks, 2 Desserts
Osaka
Hungry Osaka Street Food Tour : 15 Tastings, 4 Drinks, 2 Desserts
5.0(3,407)·3 hours
from$84/ person
via Viator
Haunted Chicago: Crime, Ghosts, and Capone Walking Tour
Chicago
Haunted Chicago: Crime, Ghosts, and Capone Walking Tour
5.0(426)·1h 30min
from$35/ person
via Viator
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Chicago
Original Chicago Architecture Interiors Tour: Dazzling Interiors
5.0(1,842)·2 hours
from$35/ person
via Viator
NYC: Flushing Chinatown Food Tour – Eat Like a Local
New York City
NYC: Flushing Chinatown Food Tour – Eat Like a Local
5.0(269)·2 hours
from$69/ person
via Viator
New Orleans Adults-Only True Crime and Ghost Walking Tour
New Orleans
New Orleans Adults-Only True Crime and Ghost Walking Tour
5.0(2,111)·1h 45min
from$38/ person
via Viator

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.

Explore more in Chicago

Architecture River CruisesSkydeck & Observation DecksCity Sightseeing & Bus ToursFood & Deep-Dish ToursGangster & History Tours