Your NPR news source
Riders seek out the cool of an evening bike trip.

Riders seek out the cool of an evening bike trip. Cook County Forest Preserves hosts an evening bike ride through Busse Woods on Aug. 26, 2023.

Justine Tobiasz

The best things to do in Chicago from Aug. 24 to Aug. 29, 2023

August may be almost over, but don’t worry — there are still plenty of summer events left in the season. Thursday brings the inaugural indie music fest Pool Party, hosted and curated by Beach Bunny frontwoman Lili Trifilio. The weekend brings more music — including a block party from one of the city’s most famous music venues — plus a car show in Berwyn, Taste of Greektown and more.

Here are five picks for the weekend and into next week.

For more ideas, see the full WBEZ Summer 250, our curated guide of 250+ events for planning the waning weeks of Chicago summer, with easy sorting to help you pick what’s right for you. You can also text “SUMMER” to 312312 for weekly picks in one of three categories: family-friendly, outdoor concerts or the best of all events.

Thalia Hall music venue at night

Thalia Hall hosts its second annual block party on Aug. 26.

K’von Jackson for WBEZ

Thalia Hall Block Party

Aug. 26

Thalia Hall is one of Chicago’s more high profile music venues, and organizers’ second annual block party promises a slew of local acts and DJs on Allport Street. On the lineup: Lady Wray, V.V. Lightbody, Smut, Modern Nun and George Arthur Calendar. 1807 S. Allport St. Free.

Busse Night Ride

Aug. 26

Ride your bike along the Busse Woods trail from sunset until dark and cap the night off with live music and a bonfire. Busse Lake Boating Center, E. Higgins Road/Route 72, east of I-290/Highway 53, Cook County. Free.

Chicken on a grill at Taste of Greektown

An array of authentic Greek food vendors prepare food at Taste of Greektown.

Courtesy of Special Events Management

Taste of Greektown

Aug. 25-27

Halsted’s most Hellenic weekend is during Taste of Greektown, where you’ll find classics like Mr. Greek Gyros and artisan baked goods from Artopolis. Hellas 2000 will grace the stage with a blend of old Greek hits and modern music. 315 S. Halsted St. $10 suggested donation.

A visitor looks at a car at the Berwyn Route 66 car show

Expect more than 175 vehicles at the Berwyn Route 66 car show.

Courtesy of Berwyn Development Corp.

Berwyn Route 66 Car Show

Aug. 26

You’ll find more than 175 pre-war and customized cars, trucks, motorcycles and even bicycles lined up along the historic Route 66 in Berwyn. The event isn’t as fussy as other car shows; award categories like “fabulous fins” and “pleasin’ paint” focus more on fun and less on mint condition rides. Elvis impersonator Rick Saucedo performs. 6746 Ogden Ave., Berwyn. Free.

Millennium Park Summer Film Series: Everything Everywhere All At Once

Aug. 29

Haven’t made it to an outdoor movie yet this season — or eager for another? Don’t miss this one. This genre-bending film swept nearly every Oscar category all at once this year, nabbing a golden statue for Michelle Yeoh, Ke Huy Quan and Jamie Lee Curtis. The plot zig-zags between worlds as one woman fights for the fate of the multiverse. Millennium Park, 201 E. Randolph St. Free.

Bianca Cseke is a digital producer at WBEZ.

The Latest
The musical, directed by Rob Ashford and set in sultry queer Savannah subcultures, promises to be a summer theatrical blockbuster. But the approach is far from traditional.
Here’s everything we know so far about season three of the hit show, which has enthralled the city and is back on Hulu on June 27.
“We read so many scripts and just couldn’t find an existing show we wanted to do,” Metcalf says of reuniting with Mantello. Steppenwolf’s artistic directors suggested they meet with Hunter about a commission.
Yes, Chicago is always a food town. But summer brings forth a particularly glorious array of handhelds, frozen delights and seasonal specials.
The city’s teen-driven, underground scene is so prolific there’s now a festival dedicated to it.