Choose Chicago

09/04/2026

Happy Friday! Chicago is packed this Labor Day weekend, from the Jazz Festival and Bike the Drive to parades, fireworks and more.

Grab your friends and soak up some fun in Chicago with our guide to events this weekend! Find local live music, comedy clubs, and community festivities.

09/04/2026

Chicago Jazz Festival 2026 is happening this weekend in Millennium Park! 🎷

A Chicago tradition for more than 40 years, the festival brings jazz legends, modern masters, and fresh voices to the city for a weekend of FREE music. The celebration also includes free neighborhood concerts and additional jazz programming throughout the city.

📍 201 E. Randolph St, Chicago
📅 Now through 9/6

🔗 Tap the link below for more info
https://www.choosechicago.com/articles/festivals-special-events/chicago-jazz-festival/

09/03/2026

Big news! The Chicago South Side & Presidential Center Shuttle by Big Bus Tours, presented in partnership by Choose Chicago and Chicago Department of Cultural Affairs and Special Events, has been extended through the end of the year, giving you more time to hop aboard downtown and explore some of the South Side’s must-see attractions.

Daily
$10 one-way, $17 all day

🔗 Tap the link below for more info and plan your South Side adventure!
https://www.bigbustours.com/en/chicago/chicago-south-side-presidential-center-shuttle

09/01/2026

Labor Day Weekend is almost here, and Chicago is not slowing down the festivals and events.

🔗 Explore ways to make the most of the long holiday weekend in Chicago: https://bit.ly/32zzofp

09/01/2026

Chicago’s free museum days in September are here. SAVE this post to plan your museum trips this month!

🔗 Tap the link below for more info!
https://www.choosechicago.com/articles/museums-art/free-museum-days-in-chicago/

09/01/2026

September in Chicago is packed with music festivals, art walks, cultural celebrations, food events, and plenty more to explore.

Looking for things to do in Chicago this month? Here's a list of top events, places to explore and restaurants to check out.

08/31/2026

ONLY in Chicago. 🥃 The official world record was just set at Recess for the most people taking a shot of Malort at once, and, of course, it was an all-out party — with IL Governor JB Pritzker included.
 

08/31/2026

From free festivals and museum days to Labor Day celebrations and Oktoberfests, here are the top free things to do in Chicago this September.

Find free things to do in Chicago this September. Find the best spot to see fireworks, free museum days, festivals, block parties and more!

08/30/2026

Chicago House Music Festival 2026 is happening NOW in Millennium Park! 🎵

Multiple stages with renowned DJs to get every house head jumpin. Head to the park Sunday to catch the tunes in the city that invented House music: 🗣️ CHICAGO

08/29/2026

Mexican Independence Day is September 16, and Chicago celebrates with vibrant Little Village traditions, authentic food, and lively festivities throughout the city.

Chicago's Mexican Independence Day is electric -- festivals, live music, cultural experiences, traditional food, and festive events that light up the whole city!