Best Things to See in Chicago (2025)

A global heavyweight that still feels personal, with Hopper, Wood, and Seurat steps from bold contemporary shows. Frequently highlighted by The New York Times and Condé Nast Traveler, it also links to Millennium Park via the Nichols Bridgeway.

The city’s definitive 90‑minute story, told by Chicago Architecture Center docents on First Lady boats. Regularly praised by national travel editors and named a top U.S. experience by readers’ polls, it runs March–November with day and evening departures.

A century of jazz and Chicago lore under emerald neon. Sets command hush, the martinis are classic, and the weekend late show swings. Celebrated by the Chicago Reader and national critics for atmosphere that’s the opposite of manufactured nostalgia.

Chicago’s independent movie palace—twinkling ceiling, 70mm screenings, festivals, and a devoted crowd. Named one of the world’s most beautiful cinemas by Time Out in 2025, with recent renovations that kept the vintage charm intact.

Always free and deeply rooted in Pilsen, this museum champions Mexican and Mexican American art with rigor and warmth. Frequently recommended by major travel editors, it pairs exhibitions with neighborhood murals just outside its doors.

Newly renovated in 2025, Intuit centers self‑taught artists—think Henry Darger alongside boundary‑pushing contemporary work. Covered by city arts writers and national outlets, it’s a focused, singular lens on Chicago’s creative history.

Jens Jensen’s “landscape art under glass” brings the tropics to the West Side—fern canyons, palms, desert blooms. Praised by local critics for its restorative calm, it’s free for Chicago residents and easy on the Green Line.

Part concert hall, part community heartbeat—the nation’s largest nonprofit music school. Expect fiddle one night, West African rhythms the next, plus family Wiggleworms and free World Music Wednesdays recommended by local listings.

A venerable jazz room near Printers Row where legends and local heavyweights share the calendar. Long recognized by jazz media and city guides, it still feels intimate—arrive early for the best sightlines.

An essential stop for Chicago blues, owned by the icon himself. Nightly sets, surprise cameos, and a January residency tradition keep it in critics’ guides and locals’ routines alike.

Run by South Side nonprofit Experimental Station, this producer‑only market champions local farms, Link Match, and community programming. Recommended by local food writers for genuine neighborhood flavor and seasonality.

Four floors in a 1917 mansion trace surgical history—from iron lungs to medical murals—mixing artifacts and contemporary art. A quirky, fascinating visit often flagged by culture editors and local critics.