Articles, Festivals & special events, Shopping and fashion
Maxwell Street Market
May 18 – Oct. 5, 2025 Free admission • Maxwell Street between Halsted Street and Union Avenue Maxwell Street Market is Chicago’s oldest market, with…
Festivals & special events
Discover the best of the city’s fests.
Festivals & special events, Food & drink
Chicago Gourmet
Sept. 25 – 28, 2025 Harris Theater Rooftop • Millennium Park Welcome to Chicago Gourmet, one of the country’s most distinguished food festivals. Each year,…
Architecture & history, Festivals & special events
Open House Chicago
Oct. 18 – 19, 2025 Free admission • Citywide One weekend. 20+ Chicago neighborhoods. 170+ places to explore. Open the door to architectural gems all…
Festivals & special events, Free & cheap, Music
Chicago SummerDance
June – September 2025 Free admission • Grant Park and parks citywide Enjoy live music and dancing on an open-air dance floor during the annual…
Festivals & special events, Free & cheap, Music
Grant Park Music Festival
June 11 — Aug. 16, 2025 Free admission • Millennium Park Experience a Chicago summer tradition like no other. The Grant Park Music Festival, now…
Architecture & history, Festivals & special events
Chicago Architecture Biennial
Sept. 12, 2025 – Feb. 28, 2026 Free admission • Chicago Cultural Center & citywide Experience the future of architecture at the 10th annual Chicago…
Festivals & special events, LGBTQ+
Chicago Pride: Your guide to Chicago Pride Parade, Pride Fest, and more
Chicago really knows how to party for Pride. Each June, the city is brimming with LGBTQ+ celebrations and events, including over-the-top street fests, exhilarating concerts,…
Festivals & special events, Free & cheap
Chicago Air and Water Show
Aug. 16 – 17, 2025 Free admission • Chicago lakefront The Chicago Air and Water Show has been an iconic Chicago event since 1959. The…
Festivals & special events
Chicago House Music Festival and Conference
Aug. 22 – 23, 2025 Free admission • Millennium Park and beyond The Chicago House Music Festival is an annual celebration of Chicago house music…
Festivals & special events, Free & cheap, Music
Chicago Blues Festival
June 5 – 8, 2025 Free admission • Millennium Park and beyond A legendary Chicago event since 1984, the Chicago Blues Festival is the world’s…
Festivals & special events, Music
Lollapalooza Chicago guide: lineup, schedule, tickets, and more
July 31 – Aug. 3, 2025 Grant Park Each year, thousands of fans travel from around the world to experience Lollapalooza in Chicago. Those lucky…
Festivals & special events, Free & cheap, Music
Chicago Jazz Festival
Aug. 28 – 31, 2025 Free admission • Millennium Park The oldest of Chicago’s free lakefront music festivals, the Chicago Jazz Festival boasts an incredibly…
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