Best May · Jun · Sep · Oct Daily spend ~$120 4 days is about right

Chicago

The best architecture in America, and it will tell you so from a boat. Brutal in January and worth every degree of the summer.

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Fast facts

Chicago in eight slides

Wikipedia · 3 Sep 2026

Ideal stay
4 days
Typical spend
~$120/day
Rough mid-range estimate
Landmarks
6 listed

Things to do

Things to do in Chicago

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Where to stay

Where to stay in Chicago

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If you only have

Chicago in a day, two days, three

  1. Day 13 stops
    1. Art Institute of Chicago
    2. Chicago Riverwalk
    3. Millennium Park
  2. Day 23 stops
    1. Navy Pier
    2. Willis Tower
    3. Wrigley Field
Landmarks

Landmarks in Chicago

Getting in

From the airport

When to go

When to go to Chicago: May or Jun or Sep or Oct

Read next

Guides about Chicago