Things to do in Chicago Tour

Things to do in Chicago Overview

There are endless things to do in Chicago, including numerous iconic buildings, fountains, parks and plazas you don’t want to miss. We share the top Chicago attractions that deserve to be on your radar when visiting.

Below is a summary of the best things to do in Chicago.

The Bean & Millennium Park

This park is one of the top things to do in Chicago and the entire state of Illinois. It is home to Cloud Gate, more commonly known as “The Bean”. Don’t miss out on a getting a photo with this iconic landmark. Full of parks, gardens, walkways, and plazas with public art, Millennium Park is a must-see for anyone visiting the Windy City. In the summer months, try to catch a free outdoor concert at the Jay Pritzker Pavilion.

Things to do in Chicago - The Bean & Millennium Park

Sears/Willis Tower

Once the tallest building in the United States, the Sears Tower is home to the highest observation deck in the country. On a clear day, you can see four states from the top, making it one of the best things to do in Chicago. In 2009, glass boxes, known as “the ledge”, were constructed, allowing visitors to see 1,350 feet below their feet. Don’t fret, these glass boxes can hold up to 10,000 lbs.

Things to do in Chicago - Sears Tower

John Hancock Center

Often mistaken for its taller, younger brother, the Sears Tower, the John Hancock Center remains one of the tallest buildings in the country, making it one of the most popular things to do in Chicago. For spectacular views of the city, visit the observation deck on the 94th floor, or go to the Signature Room, a restaurant and cocktail lounge with incredible views of the city.

Things to do in Chicago - John Hancock Center

Old St. Patrick’s Church

This Roman Catholic church, one of the most interesting things to do in Chicago, is one of the only buildings that survived the 1871 Great Chicago Fire. It’s both the oldest church and public building in the Second City. Founded in 1856 by Irish immigrants, it’s often described as the cornerstone of Irish culture in Chicago.

Things to do in Chicago - Old St. Patrick's Church

Buckingham Fountain

Located in the center of Grant Park, this intricate fountain is one of the largest ornamental fountains in the world, making it one of the top things to do in Chicago. It was built in 1927 and modeled after the Latona Fountain in Versailles. Visit the fountain at night for a dazzling colored light show.

Things to do in Chicago - Buckingham Fountain

Navy Pier

Originally called Municipal Pier #2, and built in 1916, the Navy Pier has served multiple purposes over the years. Today, it’s home to an amusement park, restaurants, boat rides, and even a greenhouse. Navy Pier, one of the most fun things to do in Chicago, is located close to numerous fascinating landmarks on Lake Michigan.

Things to do in Chicago - Navy Pier

Chicago Theatre

Built in 1921, this is the city’s most famous theatre and one of the top things to do in Chicago, located in what is considered the theatre district. The exterior features a large Tiffany stained-glass window, as well as a six-story tall arch replicating Paris’ Arc de Triomphe.

Things to do in Chicago - Chicago Theater

Second City

Second City is a world famous comedy club, theater, and improvisation school, having played a large part in the careers of comedy greats such as Bill Murray, Tina Fey, Stephen Colbert, Steve Carrell, and many others. As one of the most fun things to do in Chicago, it is home to great sketch comedy and improv. It is one of the most worthwhile items on any Chicago visitor’s to-do list.

Things to do in Chicago - The Second City

Rookery

Built in 1886, this is the oldest standing high-rise in Chicago and is one of the city’s most famous and historically significant buildings. Originally built to communicate its tenants’ wealth, it was redesigned in the early 1900s with white marble and gilded patterning to select a more modern style for that time. Explore the inside and learn all the secrets of one of the most interesting things to do in Chicago.

Things to do in Chicago - Rookery

Chicago Board of Trade

Built in 1930, this is one of the most famous art-deco buildings in Chicago and is considered to be the architectural representation of the modernization of trade. Do you recognize the Chicago Board of Trade? As one of the best things to do in Chicago, it has been featured in The Dark Knight and gangster movies, such as the Untouchables.

Things to do in Chicago - Chicago Board of Trade

Chicago Cultural Center

This often overlooked building was built in 1897 as the city’s first official public library. Today, it houses Chicago’s official city seal, is home to the largest Tiffany stained-glass dome in the world, and hosts public and private events such as concerts, charity, galas, and weddings. The Chicago Cultural Center is one of the top things to do in Chicago.

Things to do in Chicago - Chicago Cultural Center

Tribune Tower

This neo-gothic building is one of the most noticeable buildings on Chicago’s Magnificent Mile. Its other facade has pieces from some of the most iconic structures in the world, including the Taj Mahal, Parthenon, Great Pyramids of Giza, Abraham Lincoln’s Tomb, the Great Wall of China, Angkor Wat, and more, making it one of the most interesting things to do in Chicago.

Things to do in Chicago - Chicago Tribune

Trump Tower

This is the second tallest skyscraper in Chicago, third tallest in the entire country, and one of the tallest buildings in the world built without an interior metal frame. As one of the best things to do in Chicago, visit the terrace on the 16th floor for beautiful views of the Chicago River and Lake Michigan, in addition to eye-level views of 1920s building tops.

Things to do in Chicago - Trump Tower

Chicago Tour Benefits

  • Curated Sites
  • Audio Tours
  • Offline Map
  • Customizable
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Chicago Museums

Chicago Museums
Chicago museums are some of the top attractions not just in the Windy City but in the world. Check out these popular Chicago museums.

Chicago Neighborhoods

Chicago Neighborhoods
Chicago is a city of diverse neighborhoods with unique and interesting vibes. Here’s an overview of the Chicago neighborhoods you should visit.

Best Restaurants in Chicago

Best Restaurants in Chicago Tour
Chicago is a big food city, famous worldwide for its deep dish pizza. However, that isn’t the only thing to eat while visiting. Don’t miss out on the diverse selection of the best restaurants in Chicago.
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