Things to Do

Things to Do in Chicago

The essential Chicago program: Millennium Park and Cloud Gate, Museum Campus, Navy Pier and the lakefront, the city's four major-league sports venues, and the blues and jazz clubs that still play the music Chicago invented.

By the Extra Chicago editorial team·Updated Oct 20263 min read·2 sections

Photo: Gautam Krishnan / Unsplash

The short version

✓Cloud Gate — "The Bean" — in Millennium Park is free, unticketed and the closest thing Chicago has to a must-see; go at opening or after 5pm to have it to yourself.
✓Museum Campus stacks the Field Museum, Shedd Aquarium and Adler Planetarium within a ten-minute walk of each other on the lakefront — plan a full day, not an afternoon.
✓The Lakefront Trail runs roughly 18 car-free miles along Lake Michigan, and the Lincoln Park Zoo beside it is still free at the gate.
✓Four major-league venues anchor Chicago sports: Wrigley Field (Cubs, since 1916; the ballpark itself was built in 1914), Rate Field (White Sox, renamed from Guaranteed Rate Field in late 2024), United Center (Bulls and Blackhawks) and Soldier Field (Bears).
✓Chicago's blues and jazz rooms — the Green Mill in Uptown, tracing to 1907, Buddy Guy's Legends, Kingston Mines — live in this category, not a separate nightlife hub, because that's where the taxonomy landed.

The essential program: parks, museums and the lake

Start where most first visits start: Millennium Park, where Anish Kapoor's Cloud Gate reflects the skyline back at itself and the Crown Fountain and Frank Gehry's Pritzker Pavilion sit within a few minutes' walk. The Art Institute of Chicago is next door, and none of it costs anything just to look at from the plaza. Give this cluster a slow morning rather than a rushed detour — it rewards lingering more than almost anywhere else downtown.

Museum Campus is the city's other anchor, grouping three independently famous, separately ticketed institutions — the Field Museum, Shedd Aquarium and Adler Planetarium — on a lakefront spit a short walk from each other. Treat it as its own day rather than an add-on: a combined ticket often beats buying three separately, and the walk between them along the water is part of the appeal, not a chore.

white and brown city buildings during daytime

Chicago Architecture Guide

Millennium Park sits inside the city's larger architecture story.

a view of a city from the top of a skyscraper

Where to Stay in Chicago

Base yourself near the Loop or River North to walk to most of this.

Sports, blues and after dark

No single visit takes in all four major-league venues, so pick by season and interest: Wrigley Field for the Cubs' century-plus of history on the North Side, Rate Field for the White Sox on the South Side, United Center for the Bulls and Blackhawks, Soldier Field on the lakefront for the Bears. Each has its own game-day culture worth building an evening around, from rooftop clubs across from Wrigley to tailgates outside Soldier Field.

After dark, follow the blues. Chicago helped invent the electric sound, and three rooms carry that history into the present: the Green Mill, a Prohibition-era Uptown lounge with a real mob connection through Capone associate Jack McGurn, still running live jazz nightly; Buddy Guy's Legends, the blues legend's own South Loop club; and Kingston Mines in Lincoln Park, the city's oldest continuously operating blues club, with music running late. Each has a different room and a different crowd — worth more than one night if you can spare it.

Sports: Wrigley Field, Rate Field, United Center, Soldier Field.
Blues and jazz: Green Mill, Buddy Guy's Legends, Kingston Mines.
Ticket prices, game schedules and showtimes move constantly — verify before you plan an evening around any one of them.