The Great Fire of 1871 leveled most of Chicago in two days, and the city used the blank slate to invent the modern skyline. The world’s first steel-frame skyscraper went up here in 1885, and the rebuilding made Chicago one of the great capitals of American architecture, industry, and culture. I taught American history for years before I started visiting these places, and few cities reward a curious traveler the way Chicago does.
These 10 run from a working baseball cathedral to a National Park Service site that helped shape the American labor movement, with world-class museums and green spaces in between. I have noted what each place is and why it matters so you can plan with clear eyes.
Chicago Landmarks At A Glance
| Landmark | Neighborhood | Type |
|---|---|---|
| Wrigley Field | Lakeview | Ballpark / NHL |
| Willis Tower | The Loop | Skyscraper |
| The Field Museum | Museum Campus | Natural history museum |
| Millennium Park | The Loop | Public park |
| Pullman National Historical Park | Pullman | National Historical Park (NPS) |
| Art Institute of Chicago | The Loop | Art museum |
| Garfield Park Conservatory | East Garfield Park | Conservatory |
| Lincoln Park Zoo | Lincoln Park | Free zoo |
| Chicago Riverwalk | The Loop | Waterfront promenade |
| Hull-House Museum | Near West Side | Historic settlement house |
10. Hull-House Museum
We start with one of the most important sites in the history of American social reform. The Jane Addams Hull-House Museum on the Near West Side preserves the settlement house that Jane Addams and Ellen Gates Starr founded in 1889 to serve Chicago’s immigrant neighborhoods.
At its height, Hull-House offered classes, childcare, a kitchen, and a meeting place for thousands of newcomers each week. Addams went on to win the Nobel Peace Prize in 1931, the first American woman to do so. Today the original house, now part of the University of Illinois Chicago, is a free museum that tells the story of the settlement movement and the women who led it.
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9. Chicago Riverwalk
At number nine is one of the best ways to see the city from the water’s edge. The Chicago Riverwalk is a pedestrian promenade running along the south bank of the main branch of the Chicago River, built out in stages and largely completed in the 2010s.
The walkway turned a working river into a public space lined with restaurants, kayak launches, and prime views of the city’s celebrated architecture. An architecture boat tour from here is one of the finest introductions to Chicago you can get. Come at sunset, when the buildings catch the light and the water glows.
8. Lincoln Park Zoo
Number eight is a rare thing in modern America, a major zoo that is still free to the public. The Lincoln Park Zoo, founded in 1868, is one of the oldest zoos in the country and sits on the lakefront just north of downtown.
The zoo is home to lions, gorillas, and hundreds of other animals, along with a historic Victorian conservatory and the Farm-in-the-Zoo. It draws millions of visitors a year, and admission costs nothing, a gift to the city that has lasted more than 150 years. It pairs perfectly with a walk through Lincoln Park itself.
7. Garfield Park Conservatory
At number seven is one of the largest conservatories in the country. The Garfield Park Conservatory opened in 1908, designed by Jens Jensen to resemble a great Midwestern haystack, and it has been called landscape art under glass.
Inside its greenhouses you will find a palm house, a fern room, a desert house, and rotating seasonal displays, all spread across roughly two acres under glass. Like the Lincoln Park Zoo, it is free to enter. On a gray Chicago winter day, stepping into its warm, green rooms is one of the best things you can do in the city.
6. Art Institute Of Chicago
Number six is one of the finest art museums in the world. The Art Institute of Chicago, founded in 1879 and guarded by its famous pair of bronze lions on Michigan Avenue, holds a collection that spans thousands of years.
It is especially renowned for its Impressionist and Post-Impressionist holdings, including Georges Seurat’s A Sunday on La Grande Jatte and Grant Wood’s American Gothic, along with Edward Hopper’s Nighthawks. Give yourself the better part of a day. This is one of the great cultural destinations in the country.
5. Pullman National Historical Park
At number five is the one National Park Service site on this list, and one of the most important labor history sites in America. Pullman was built in the 1880s by railcar magnate George Pullman as a model company town for the workers who built his luxury sleeping cars.
In 1894, after Pullman cut wages without cutting rents, his workers walked out. The Pullman Strike spread into a nationwide railroad boycott led by Eugene V. Debs and was broken only when the federal government sent in troops. The episode reshaped the American labor movement and helped lead to the creation of Labor Day.
President Obama designated the district a National Monument in 2015, the first Park Service unit in Chicago, and Congress redesignated it Pullman National Historical Park in December 2022. The visitor center in the old administration building and the surviving red-brick rowhouses let you walk straight into that history.
4. Millennium Park
Number four is the city’s modern showpiece. Millennium Park opened in 2004 on what had been railroad land at the edge of the Loop, and it quickly became one of the most visited attractions in the Midwest.
Its centerpiece is Anish Kapoor’s Cloud Gate, the mirror-polished sculpture everyone calls the Bean, which reflects the skyline and the crowds in its curves. Add the Jay Pritzker Pavilion designed by Frank Gehry and the Crown Fountain, and you have a public space that defines contemporary Chicago. It is free and open year-round.
3. The Field Museum
At number three is one of the great natural history museums on earth. The Field Museum grew out of the 1893 World’s Columbian Exposition and today anchors the lakefront Museum Campus with collections of more than 40 million specimens.
Its most famous resident is Sue, the largest and most complete Tyrannosaurus rex skeleton ever found. Beyond the dinosaurs you will find ancient Egyptian galleries, gems, and exhibits drawn from cultures around the world. Plan on most of a day, and pair it with the neighboring Shedd Aquarium and Adler Planetarium if you have time.
2. Willis Tower
Number two is the building that long defined the Chicago skyline. Completed in 1973 as the Sears Tower and renamed Willis Tower in 2009, it stood as the tallest building in the world for nearly 25 years and remains one of the tallest in the Western Hemisphere.
Its bundled-tube structural design was a Chicago engineering innovation that changed how tall buildings are built. The Skydeck on the 103rd floor offers sweeping views, and the glass-floored Ledge boxes let the brave stand more than 1,300 feet above the street. On a clear day you can see four states.
1. Wrigley Field
Topping the list is a true cathedral of American sport. Wrigley Field opened in 1914, which makes it the second-oldest ballpark in Major League Baseball after Boston’s Fenway Park, and the home of the Chicago Cubs since 1916.
The ivy-covered outfield walls, the hand-turned scoreboard, and the rooftop seats across the street are baseball history made tangible. In 2016 the Cubs ended a 108-year championship drought here, one of the most cherished moments in the sport. Wrigley was designated a National Historic Landmark in 2020. Catch a day game, and you understand why it tops the list.
More Things To Do
Chicago rewards travelers who keep exploring. If you are planning a wider trip, here are a few ways to go further:
- Compare Chicago’s landmarks with the best of other great American cities in our guides to New York Landmarks, San Francisco Landmarks, and Dallas Landmarks.
However you build your trip, give Chicago the time it deserves. These 10 landmarks are a strong start, and each one connects to a larger chapter in the story of this remarkable city.
