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🇺🇸United States of America

Two days in Chicago
2 day travel itinerary

by TripMapper

Get blown away by the 'Windy City'!

2 Days
Image by Aveedibya Dey on Unsplash
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Image by TripMapper Ltd on Unsplash

From its iconic architecture to its mouthwatering deep-dish pizza and world-class art to urban sandy beaches, Chicago offers diverse experiences for all.

First and foremost, Chicago is a city with a rich architectural heritage. One of the must-do activities in Chicago is taking an architectural cruise, which provides a unique perspective on the stunning skyscrapers designed by architectural legends like Frank Lloyd Wright and Jeanne Gang.

For culinary enthusiasts, Chicago is a paradise. The city is renowned worldwide for its deep-dish pizza, an experience that's quintessentially Chicagoan! Beyond pizza, Chicago offers a diverse culinary scene that includes everything from gourmet restaurants to street food vendors.

Art and culture thrive in Chicago, with world-class museums such as the Art Institute of Chicago, which boasts an extensive collection spanning various eras and cultures. The Museum of Contemporary Art and the Field Museum further enrich the cultural landscape, ensuring that art enthusiasts have plenty to explore.

This city is a haven for sports enthusiasts, offering the chance to catch games and matches year-round. Sports fans can cheer on the Chicago Cubs at historic Wrigley Field, watch the Chicago Bulls in action at the United Center, or attend a Chicago Bears football game. The city's passion for sports is infectious!

For those looking to unwind, Oak Street Beach provides a picturesque escape along Lake Michigan's shoreline. Whether you want to sunbathe, swim, or simply enjoy the views of the lake and the city's skyline, it's a tranquil oasis amidst the urban bustle.

There is little wonder that Condé Nast Traveler readers voted Chicago the Best Big City in the U.S.A. for seven years in a row!

Use TripMapper as your trip organizer. If you are in need of a little inspiration to get you started click 'Customise' to use our interactive Chicago itinerary (below) for the best things to see and do in Chicago - then customise to make your own!

By combining both a trip itinerary app and a travel budget app, TripMapper is the best travel itinerary app to help you craft your perfect trip! Our vacation planner is available on the web and on mobile.

* Please check all relevant government guidance prior to, and during, your travels. Please also check any opening & closing times for all establishments contained within our itinerary. Find our Terms of Service here.

Itinerary Highlights

  • Explore Chicago's stunning skyline and architectural landmarks on a boat tour along the Chicago River
  • Savour the city's signature dish by trying a slice of deep dish pizza
  • Experience world-class shopping along Michigan Avenue's Magnificent Mile, home to luxury boutiques and department stores
  • Enjoy some sun and sand along Lake Michigan's shoreline at Oak Street Beach
  • Explore Millennium Park with iconic attractions like the Cloud Gate sculpture ("The Bean"), Crown Fountain, and beautiful gardens
  • Immerse yourself in the sports culture of Chicago by attending a Chicago bulls game or a Chicago Cubs baseball game at historic Wrigley Field
  • Grab a Divvy Bike and cycle along the Lakefront Trail which offering picturesque views of the city
  • Explore the Art Institute of Chicago, one of the oldest and largest art museums in the United States
  • Have a cocktail or two whilst enjoying a spectacular view from LH Rooftop at LondonHouse Chicago