Two Days in Chicago, a Detailed Itinerary for 2024

Planning to spend 2 days in Chicago? Chicago, dubbed as the Windy City, and the third-largest city in the United States, is the birthplace of the skyscraper. 

It’s a huge vibrant city with an incredible buzzing energy and a unique vibe, the perfect multicultural melting pot, and some of the best architecture you’ll ever lay your eyes on.

Spending 2 days in Chicago and seeing all the major attractions is very doable, as you’ll be exploring the incredibly diverse neighborhoods, and the museums.

Chicago in 2 Days: Day One

Art Institute of Chicago

Start your first day by exploring the artsy side of Chicago by visiting the second-largest art museum in all of the country.

The Cloud Gate Sculpture

Better known as “The Bean”, this sculpture is not only one of the highlights of Millennium Park but of all of Chicago.

Architectural River Cruise

As you sit in open-air seating with a great sound system, and a full-service bar, you’ll slowly pass by more than 50 buildings along the Chicago River.

The Magnificent Mile

Now it’ll be time to walk The Magnificent Mile! One of Chicago’s most dynamic areas stretches between Lake Shore Drive and the Chicago River.

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