10 Can’t Miss Outdoor Events In Illinois As Summer Winds Down

ILLINOIS — Summer is winding down in Illinois, but there are still some good opportunities to make the most of warm days and long nights before cooler weather sets in and the calendar fills up with fall activities.

The “end-of-the-summer scaries” is a real term for the anxiety and dread that people may feel as the season comes to a close, and they realize they didn’t pack in as much fun as they intended.

As a prescription for end-of-summer malaise, we’ve rounded up 10 things to do outside to enjoy the last bits of summer sunshine.

Are you planning an event this fall? Feature it so nearby readers see it all across Patch — including in roundups like this!

Here are some upcoming outdoor events you shouldn’t miss:

Skokie Backlot Bash 2025

Hundreds will flood downtown Skokie for the 2025 Backlot Bash Aug. 22-24, featuring live music, a carnival and a 5k run. The 2025 Backlot Bash will be the 18th edition of the event, which is organized by the Skokie Park District in partnership with the village, the public library, the local high school district and chamber of commerce.

Route 66’s Wine, Jazz, & Art Fest

Join your friends , Saturday August 23rd at the Billie Limacher Bicentennial Park & Theater in Joliet, IL on the lawn and enjoy an afternoon and evening at the Illinois Rock & Roll Museum on Route 66’s 4th Annual Wine, Jazz, & Art Fest with food & beverage vendors.

Chicago Gaelic Park Irish Fest

Gaelic Park is very excited to host Chicago Gaelic Park Irish Fest once again! We look forward to this multi-generational event which has been a staple for the Irish American community in Chicago for over 35 years. The event will take place Aug. 22-24 at Chicago Gaelic Park, 6119 147th St, Oak Forest.

Will County Fair

The Will County Fair started on Aug 20 and will run until Aug. 23 at the Will County Fairgrounds, 710 W South St. in Peotone. Featuring a demolition derby, tractor and truck pull, baby show, chili cookoff and more. Find the full schedule of events on the website.

Naperville Jaycees' Last Fling

Naperville Jaycees' Last Fling takes place in and around downtown Naperville from Aug. 31 to Sept. 1. Free-to-attend event. Features live music, Labor Day parade, carnival, food vendors and more.

Taste of Chicago

The 45th annual Taste of Chicagowill kick off Sept. 5 at GrantPark and will run through Sept. 7. The event is known for bringing some of the city's most iconic bites together in one place. The free event will allow attendees to enjoy live music performances, community dance lessons, family-friendly activities, interactive pop-ups, and so much more.

Randolph Street Market's Vintage Shindig

The world-famous “mecca of cool,” Randolph Street Market Festival, is returning to downtown Highland Park with a Three in One "Vintage Shindig" market on Saturday, September 13 and Sunday, September 14 from 10 AM–5 PM at the Highland Park Community House (1991 Sheridan Road) and
The Art Center Highland Park (1957 Sheridan Road).

Tacos and Tequila Festival

This 21+ event takes place at Northwestern Medicine Field on Sept. 20 and will feature your favorite throwback artists, including Ludacris, Timbaland and Trina. Attendees will chow down on the area’s best chef-inspired taco vendors throughout the festival. Wash those tacos down with some margs and tequila.

Chicago Live!

The Largest Free Performing Arts Festival in the Midwest returns this September! Navy Pier’s free two-day Chicago Live! performing arts festival returns for the fifth year on September 20-21, showcasing the best of Chicago’s vibrant arts and cultural community.

Oktoberfest Chicago

Get ready to raise your steins and don your dirndls—St. Alphonsus Oktoberfest is back and bringing a taste of Germany to the heart of Chicago! From September 26-28, this legendary 22nd annual festival transforms the intersection of Lincoln/Southport/Wellington into a buzzing Bavarian beer hall, complete with live oompah bands, frothy brews, and mouthwatering bratwursts.