Things to Do in Chicago (2025)

Old‑school swagger, live jazz seven nights, cash only, and a neighborhood crowd that still shushes talkers. Frequently spotlighted by Condé Nast Traveler and Choose Chicago, it’s the city’s enduring jazz heartbeat with real Uptown grit and grace.

Chicago’s art‑house temple: 35mm and 70mm series, midnight cult shows, and a live organ prelude. Lauded by Chicago Reader and covered by the Sun‑Times for recent upgrades, its 2025 repertory slate proves why cinephiles treat it like a second home.

A family’s devotion to Jaliscan goat birria—hand‑tortillas, consommé, and salsa de molcajete—earns steady praise from the Michelin Guide and local critics. The Uptown location is currently serving while the original Archer Heights spot recovers from a 2025 fire.

South Side rib tips, hot links, and the city’s famed aquarium smoker define this Black‑owned landmark, honored with the James Beard Foundation’s 2025 America’s Classics award and celebrated by local press for seven decades of Chicago‑style barbecue.

One of Illinois’ last wood‑smoke seafood houses—cash only, curbside picnics by the 95th Street bridge. A James Beard America’s Classics winner that rebuilt and reopened in 2024, its smoked shrimp and chubs remain South Deering rituals.

Black‑woman‑founded, community‑driven, and newly reopened with a cafe in West Town. Celebrated by local outlets and national media for literacy work, Semicolon hosts author events and art shows that center voices the city needs.

Bridgeport’s beloved slashie blends a neighborhood bottle shop with a progressive bar program and community events. Often recommended by Time Out and profiled by local reporters, Maria’s keeps South Side culture front and center—patio pop‑ups included.

A modern, Black‑owned winery‑restaurant from community builders behind The Silver Room, pairing a serious bottle list with live music and DJ nights. Praised by local food critics for hospitality that feels like Bronzeville today and tomorrow.

A globally respected record shop for jazz, soul, Latin, funk, and beyond—shouted out by Rolling Stone and The New York Times. New arrivals hit daily; staff picks and the bargain basement are catnip for crate diggers.

Since 1957, this nonprofit has taught Chicago to play—and hosts intimate concerts where legends and locals share the stage. Frequently covered by Chicago media, its 2025 calendar ranges from bluegrass to global sounds with a welcoming, all‑ages vibe.

The city’s flagship blues club, founded by the man himself. The stage hosts Chicago stalwarts and national headliners; January residencies are lore. Endorsed by the Chicago Blues Guide and tourism pros, it’s essential listening near the Loop.

Pork slow‑cooked Michoacán‑style, served by the pound with heirloom‑corn tortillas. Celebrated by the Michelin Guide and recently profiled by NBC Chicago for its expansion, this family operation has defined Chicago carnitas since 1975.