Best Things to Do in Chicago

Chicago's big sights are grouped tightly around the Loop and the lakefront, so a first visit can cover a lot on foot. Here's our list, in rough order of priority.

1. The architecture river cruise. Ninety minutes on the Chicago River with a guide from the Chicago Architecture Center, past more than a century of skyscrapers. If you do one paid thing, make it this. See our architecture guide.
2. The Art Institute of Chicago. Seurat's A Sunday on La Grande Jatte, Hopper's Nighthawks and Grant Wood's American Gothic, plus one of the finest Impressionist collections outside Paris. Our museums guide has a plan.
3. Millennium Park. Anish Kapoor's Cloud Gate, the polished steel sculpture everyone calls the Bean, the Crown Fountain with its giant video faces, and free summer concerts at Frank Gehry's bandshell.
4. The lakefront. Walk or cycle the Lakefront Trail north from Navy Pier to North Avenue Beach, where the skyline rises straight behind the sand.
5. The view from the top. Willis Tower's Skydeck has glass boxes that stick out from the 103rd floor. 360 Chicago, in the former John Hancock Center, has the better view of the lake and the Gold Coast.
6. The Chicago Cultural Center. A free, grand old library building on Michigan Avenue with a Tiffany glass dome. It is also the last stop on the Loop walk in our architecture guide, so there is no need for a separate trip.
7. The Riverwalk. A path along the south bank of the main branch of the river, with bars, boat docks and kayak hire, lined by the towers the cruise shows you from the water.
8. Wrigley Field. Built in 1914 and home to the Cubs since 1916, with ivy on the outfield walls. A summer afternoon game in the bleachers is a Chicago institution, and the bars of Wrigleyville fill up before and after.
9. The Obama Presidential Center. Opened in Jackson Park in June 2026, with a museum on the Obama presidency and free gardens and public spaces around it. The museum needs a timed ticket.
10. The Museum of Science and Industry. A German U-boat, a working replica coal mine and a building left over from the 1893 World's Fair, in Hyde Park near the Obama Center.
11. Live blues and jazz. Kingston Mines in Lincoln Park keeps the latest hours, Buddy Guy's Legends in the South Loop draws bigger names, and the Green Mill in Uptown is the classic jazz room. Expect a cover charge.
12. A neighbourhood for dinner. The West Loop for ambitious restaurants, Pilsen for Mexican food and murals, Logan Square for bars. See our food guide.

What we'd skip: most of Navy Pier, which is a crowded strip of chain restaurants and rides (walk to the end for the skyline view, then leave), and queuing for deep-dish pizza on a Saturday night when a fifteen-minute L ride takes you somewhere quieter.