Family, Itineraries
Top Chicago must-dos with teens or tweens
A family vacation to Chicago will be anything but basic. And it’s an especially perfect destination if you have teens and tweens in tow. Chicago…
Articles
Sports & recreation
Chicago Fire soccer
Chicago’s sports scene is always smoldering — and the Chicago Fire Football Club know exactly how to turn up the heat. The Chicago Fire have…
Festivals & special events, Free & cheap
Chicago Air and Water Show
Aug. 15 – 16, 2026 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. 27 – 30, 2026 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 Jazz Festival
Sept. 3 – 6, 2026 Free admission • Millennium Park The oldest of Chicago’s free lakefront music festivals, the Chicago Jazz Festival boasts an incredibly…
Festivals & special events, Free & cheap, Music
World Music Festival Chicago
Sept. 25 – Oct. 4, 2026 Free admission • Multiple locations The 26th annual World Music Festival is your passport to musical acts from across…
Festivals & special events, Food & drink
Taste of Chicago
July 8 – 12, 2026 Free admission • Grant Park and citywide The 46th annual Taste of Chicago is bringing some of the city’s most…
Festivals & special events, Free & cheap, Music
Chicago Gospel Music Festival
July 24 – 25, 2026 Free admission • Millennium Park Gospel music has deep roots in Chicago. The Chicago Gospel Music Festival, one of the…
Festivals & special events, Music, Parks & outdoors
Millennium Park Summer Music Series
Select Mondays and Thursdays June 15 – Aug. 6, 2026 Free admission • Millennium Park The Millennium Park Summer Music Series offers free outdoor concerts…
Entertainment, Festivals & special events, Parks & outdoors
Millennium Park Summer Film Series
Tuesdays, July 1 – Aug. 19, 2026 Free admission • Millennium Park Every summer in Chicago, visitors and locals flock to the Jay Pritzker Pavilion…
Festivals & special events, Free & cheap, Music
Chicago Blues Festival
June 4 – 7, 2026 Free admission • Millennium Park and beyond A legendary Chicago event since 1984, the Chicago Blues Festival is the world’s…
Dining, Holidays
35+ romantic restaurants for Valentine’s Day dinner in Chicago
The biggest date night of the year is coming up, and the city’s restaurants are pulling out all the stops so you and your date…
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