Top 10 Things to Do in Chicago

Chicago is consistently ranked among the world’s great cities for livability, and it rewards visitors with a seriousness and depth that many American tourist destinations don’t offer. The architecture is extraordinary, the food scene is among the best in the country, the museums are world-class, and the lakefront provides a natural amenity that transforms the experience of the city in good weather. These top 10 represent the experiences that most visitors leave Chicago having wished they’d made time for.

1. Take an Architecture Boat Tour

Chicago is arguably the most architecturally significant city in the United States — the birthplace of the skyscraper, home to seminal buildings by Louis Sullivan, Daniel Burnham, Ludwig Mies van der Rohe, and dozens of other major architects.

The Chicago Architecture Center river boat tours are among the best urban architecture experiences in the world: a 90-minute narrated cruise along the Chicago River with direct views of the city’s landmark buildings from the water. It is the single best introduction to why Chicago looks the way it does and why that matters.

2. Walk the Lakefront Trail

The Chicago Lakefront Trail runs 18 miles along Lake Michigan, and any portion of it is worth visiting. The view of the downtown skyline from the lakefront — particularly from North Avenue Beach or Montrose Harbor — is one of the most dramatic urban panoramas in North America. On warm days, the lakefront is where the city congregates, and the energy of it is one of Chicago’s most distinctive qualities.

3. Visit the Art Institute of Chicago

The Art Institute of Chicago is one of the great museums of the world, with a permanent collection that includes George Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, and extensive Asian art, decorative arts, and architectural drawings collections. The Modern Wing, designed by Renzo Piano and opened in 2009, is among the most beautiful gallery spaces in the country. Allow at least three hours; a full day is better.

4. Eat Deep-Dish Pizza (and Know It’s Not the Whole Story)

Chicago deep-dish pizza — made in a deep pan with the sauce on top of the cheese — is the dish most associated with the city and worth trying once at Giordano’s, Lou Malnati’s, or Pequod’s (which many Chicagoans prefer). But locals are equally passionate about Chicago-style thin crust, and the city’s food scene beyond pizza — its Michelin-starred restaurants, its Mexican and Chinese immigrant food communities, its steakhouses, its hot dog culture (never with ketchup) — is one of the best in the United States.

5. See the Cloud Gate (The Bean) in Millennium Park

Anish Kapoor’s Cloud Gate — universally known as “The Bean” — is a 110-ton stainless steel sculpture that reflects the Chicago skyline and the people surrounding it in its curved surface. It is one of the few major public sculptures in any American city that lives up to its reputation: it is genuinely interesting at close range, changes as you move around it, and is worth the visit even for people who are skeptical of public sculpture.

Millennium Park surrounding it includes the Jay Pritzker Pavilion (Frank Gehry’s outdoor concert shell) and is one of America’s best urban parks.

6. Explore the Chicago Blues and Jazz Scene

Chicago is one of the great American blues cities — the destination of the Great Migration that brought Delta blues north and transformed it into the electric Chicago blues style of Muddy Waters, Howlin’ Wolf, and Willie Dixon. Rosa’s Lounge, Buddy Guy’s Legends, and Andy’s Jazz Club are among the best options for live blues and jazz. The Chicago Blues Festival each June is one of the largest free music festivals in the country.

7. Visit the Museum of Science and Industry

The Museum of Science and Industry is one of the largest science museums in the Western Hemisphere and one of the best in the world for visitors of all ages. Permanent exhibits include a German U-boat captured in 1944 (the U-505), a working coal mine, a simulated weather observation station, and a coal car sized train you can ride. The building itself — the former Palace of Fine Arts from the 1893 World’s Columbian Exposition — is architecturally significant.

8. Walk the Chicago Riverwalk

The Chicago Riverwalk is a pedestrian path running along the main branch of the Chicago River through downtown, with outdoor restaurants, bars, kayak rentals, and excellent views of the bridge architecture above. It’s at its best from May through October and provides a different perspective on downtown Chicago than either the lakefront or the elevated train — quieter, more intimate, and architecturally rich.

9. Visit the Wrigley Field Neighborhood

Even if there’s no game, the Wrigley Field neighborhood — Wrigleyville — is worth a visit. The stadium itself (built in 1914) is one of the most beautiful in Major League Baseball, and going to a Cubs game is one of the most specifically Chicago experiences available. If there’s no game, the surrounding streets of Wrigleyville and the adjacent Lakeview neighborhood offer good bars, restaurants, and the particular atmosphere of a neighborhood organized around a century-old ballpark.

10. Explore a Neighborhood Beyond Downtown

Chicago’s greatest strength as a city is the quality and variety of its neighborhoods, most of which visitors never reach.

Pilsen’s Mexican murals and art galleries. Andersonville’s Scandinavian heritage and independent shops. Hyde Park and the University of Chicago’s Gothic campus. Logan Square’s restaurant scene. Bridgeport, the historically Irish neighborhood on the South Side.

The best Chicago experience involves leaving the Loop and the tourist corridor to see what the city is actually made of — which is neighborhoods with distinct character, long histories, and the kind of specific, un-touristy life that makes a city genuinely great rather than merely spectacular.