Chicagoans know how to stretch out summer, and this September the celebration heads to Bridgeview for Summer’s Last Dance. The one-day festival lands on Saturday, September 20, 2025, transforming the Summer’s Last Dance Festival Grounds into a day-to-night showcase of music, food, and community. Gates open at 11 a.m., with performances running until 11 p.m.

The Chicago Bears are moving forward with plans to build a state-of-the-art stadium in Arlington Heights, a project set to reshape the team’s future and potentially bring the Super Bowl to Illinois as early as 2031.

10 fun things to do in Chicago this Labor Day Weekend 2025

Chicago officials have broken ground on Concourse D , a $1.3 billion expansion at O’Hare International Airport that marks the first new concourse in more than 30 years.

The Chicago Cubs will debut their inaugural Oktoberfest with the Cubs this fall, a three-day festival set for September 19–21, 2025, in the Toyota Camry Lot at 1126 W. Grace Street, directly north of Wrigley Field. The event will feature beer tents, authentic German cuisine, carnival rides, live entertainment, and activities for visitors of all ages.

Chicago is gearing up for a baseball event unlike any other as the Savannah Bananas bring their wildly popular “Banana Ball” to the city for the first time. The team will play at Guaranteed Rate Field on Friday, August 15, and Saturday, August 16, 2025, with both games starting at 7 p.m.

Chicago officially declared August 8 as Patrick Kane Day, honoring the legendary former Blackhawks star and his iconic No. 88 jersey. The date, 8/8, was chosen to reflect Kane’s number and his lasting impact on the city during his time with the team.

CHICAGO — The 2025 Chicago Air & Water Show is set to return to the city’s lakefront on Saturday, August 16, and Sunday, August 17, from 10:30 a.m. to 3:00 p.m. each day. A full rehearsal is scheduled for Friday, August 15.

CHICAGO — Air quality in Chicago plummeted this week to some of the worst levels in the world, with officials reporting “very unhealthy” conditions due to smoke from Canadian wildfires blanketing the region.