Best Things to Do in Chicago This Weekend — Music, Sports & Food

May 2026

From house music's birthplace to deep-dish pizza, here's your weekend in Chicago.

Concerts & Live Music

United Center, Wrigley Field (summer stadium shows), Chicago Theatre, Aragon Ballroom, Metro, Empty Bottle, Schubas. Chicago invented house music — Smartbar at Metro and Spybar still keep that tradition alive. Jazz at the Green Mill (the Al Capone hangout) is a Chicago institution.

Sports Calendar

Cubs (Wrigley Field) and White Sox (Guaranteed Rate Field) for baseball April–October. Bears (Soldier Field) for football. Bulls and Blackhawks (United Center) for basketball and hockey. Fire (Chicago Fire FC at Soldier Field) for soccer. Almost every weekend has at least one game.

Architecture Boat Tour

The Chicago Architecture Center river cruise is the city's #1 rated activity. 90 minutes, narrated, with a beer in hand. Book through NearEvent — Klook usually has it for less than buying direct. Best at golden hour.

Festival Season

Lollapalooza (Grant Park, August), Pitchfork (July), Riot Fest (September), Chicago Blues Festival (June, free). Add the Air & Water Show in August and Chicago is basically a festival city May–September.

Deep Dish vs Thin Crust

Lou Malnati's, Pequod's (caramelized crust — the local pick), Pizzeria Uno. Chicago also has world-class thin crust: Vito & Nick's, Pat's Pizza. Don't skip the tavern-cut squares — they're the actual Chicago native style.