Chicago is known for historic buildings and outdoor spaces that capture the cultural and architectural diversity of the city. With landmark destinations in business, recreation, sports, and the arts, the Windy City is home to a wide range of fascinating and fun historical sites. Whether you’re a resident or a guest, we put together a list of some of the top historic landmarks in Chicago to help you plan your next outing or trip.

Wrigley Field

Entry sign to Wrigley Field in Chicago.
Image via Flickr by aaronHwarren Licensed CC BY-ND 2.0

Wrigley Field opened in 1914 when the first major league baseball game pitted the home team, the Federals, against the Kansas City Packers. William Wrigley — of chewing gum fame — purchased the property and the new home team, the Cubs, started playing in the stadium. The field offers tours on game and non-game days with varying sights. Tours last up to 90 minutes with walkthroughs of the bleachers and the field. When there’s no game in session, you can visit the press box, visitor’s clubhouse, and the dugout. This iconic place is a must-see for sports fans and history buffs alike.

Tribune Tower

The Tribune Tower represents Chicago architecture at its best. Built to house the paper’s headquarters, the tower was built and rebuilt in the gothic revival style with traces of art deco design. Embedded in the outer walls of this architectural wonder are over 100 rocks, stones, and architecture fragments from around the world. Walk the building’s perimeter to find pieces of stone and other materials with historical significance such as a piece of the Giza Pyramids, a steel beam from the World Trade Center, or even a fragment of the Berlin Wall.

Millennium Park

Located in The Loop section of downtown Chicago, this sprawling park complex offers visitors plenty to do and see. From world-famous art installations to gardens and amphitheaters, Millennium Park is a landmark area to explore. Visit the Lurie Garden for seasonal blooms and free guided tours through this natural haven. The McCormick Tribune Plaza transforms from an ice skating rink in the colder months to the Park Grill, complete with alfresco dining during warmer days. Enjoy open-air entertainment at the Jay Pritzger Pavilion and Great Lawn or take in a public art exhibition at the outdoor Boeing Galleries.

Other can’t-miss sights in and around the park include Crown Fountain, an interactive water display by artist Juame Plensa, featuring the faces of Chicago citizens. It’s also worth the trek to Maggie Daley Park, an extension of Millennium, which features a children’s area with imaginative play structures and a natural area dubbed the “Enchanted Forest.” This unique recreational site also features The Ribbon ice skating course, an elongated track made to give skaters the feel of traveling on an Alpine track and a rock-climbing wall capable of hosting up to 100 climbers at a time.

Cloud Gate at Millennium Park

This iconic sculpture, located within Millennium Park, is a must-see on your Chicago tour. Take a stroll through the park to get close to “The Bean” for pictures and contemplation. Artist Anish Kapoor designed this piece of public art to reflect the Chicago skyline, natural park surroundings, and people of the city. Inspired by the fluid shine of liquid mercury, Cloud Gate encourages visitors to view their own reflections and touch its silvery surface. The art installation rises 33 feet high and extends 66 feet long, making this reflective landmark an interactive experience to explore on your park tour.

Union Station

Opened in 1925, Union Station connects passengers to inner-city and destination trains within the Amtrack-owned station. Historic architecture makes this busy city hub a destination for anyone in search of a landmark site. Step into the Great Hall to view the immense pubic waiting space decked with ornate furnishings and its iconic barrel-vaulted skylight spanning over 200 feet. Named for the union of four railroads necessary to centralize the constant rail traffic in and out of Chicago, the structure continues to evolve to meet the needs of the city. Union Station also houses restaurants, shops, and event spaces.

Navy Pier

Chicago’s Navy Pier has offered visitors and residents alike a rollicking good time since 1916. Filled with amusements, food and beverage establishments, and live entertainment venues, Navy Pier is one of Chicago’s most beloved landmarks. Enjoy vintage and modern rides at Pier Park, including the Centennial Wheel and a carousel with furnishings made to look like you’re spinning through the 1920s. Navy Pier is also home to the Chicago Shakespeare Theater, which hosts hundreds of performances every year. You’ll also find the Children’s Museum, Funhouse Maze, and Time Freak game — fun for kids of all ages.

Other popular activities at the Pier include the boat cruises offering tours of Lake Michigan and the Chicago River. Themed cruises, peaceful sightseeing trips, and adventure tours set sail daily. Navy Pier also offers a sampling of some of Chicago’s best fare with classic deep-dish pizza from Giordano’s, signature sweets like the rainbow cone, and the famous Garrett’s Popcorn. It’s also a great place to order a Chicago-style hot dog.

Skydeck Chicago at Willis Tower

You don’t want to miss the nation’s tallest observation deck in the landmark Willis Tower. Skydeck Chicago gives visitors a truly immersive Chicago experience with more than just views. Start your visit to the museum below where you’ll learn more about the history and architecture of one of the world’s most famous cities. Board a replica “L” train with digital window displays that show you the city neighborhoods, then disembark to grab your picture with a giant deep-dish pizza or 9-foot-long hot dog.

After your downstairs tour, it’s time to glide up 103 floors to the observation deck. On a clear day, you can see four states in the panoramic viewing area plus astounding views of the city skyline and streets below. Step out on The Ledge, a one-of-a-kind glass-floored balcony where you can look down from 1,353 feet.

With so many world-famous destinations to choose from, we wanted to give you a taste of some of the best historic landmarks to visit in Chicago. Contact us to share your favorites for our next list. At American Auto Insurance, we provide low-cost auto insurance to give you the coverage you need on the road. Call 800-483-4868 to speak with one of our expert agents in the Chicago area today.


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