Chicago Gourmet

September 25–27 | Times Vary | The Loop, The Harris Theater for Music and Dance (205 E Randolph Drive)

Chicago Gourmet is back for another incredible year! This year’s theme, “Let Your Tastebuds Dance,” celebrates the shared energy and passion of food and dance. Powered by Invesco QQQ, one of the nation’s premier culinary festivals, the event is turning up the tempo in 2026 with an ensemble of award-winning chefs and a vibrant lineup of dance-inspired events.

Learn More →

White Sox vs. Rockies

September 25–27 | Times Vary | Bridgeport, Guaranteed Rate Field (333 W 35th St)

Come cheer on the White Sox!

Learn More →

Hyde Park Jazz Fest

September 26–27 | Times Vary | Hyde Park, Locations Vary

The Hyde Park Jazz Festival returns across multiple Hyde Park venues on Chicago’s South Side. The festival is free, although organizers welcome a $10 donation. Enjoy a weekend of jazz throughout this vibrant South Side neighborhood.

WingOut Chicago

September 18–20 | Times Vary | Wrigleyville, Gallagher Way (3635 North Clark Street)

This unforgettable festival brings together the city’s finest wing-slingers for a weekend of wing sampling, live music, adult beverages, competitions, and more.

Learn More →

Randolph Street Market

September 26–27 | Times Vary | West Loop (1341 W Randolph Street)

Find the best art, antiques and vintage decor, ephemera, vintage and indie designer fashion and jewelry, vinyl, global goods, fancy and fun foods – thousands of top-quality goods presented by dealers from around the country at this fancy European-style flea market festival!

Learn More →

NHL Pre-Season: Blackhawks vs. Blues

September 26 | 6:00 PM | West Loop, United Center (1901 W Madison St)

Hockey season is almost back! Come cheer on the Blackhawks as they take on the St. Louis Blues in this pre-season game.

Learn More →

President's Cup

September 25–27 | Times Vary | Medinah, Medinah Country Club (6N001 Medinah Road)

Witness history as Brandt Snedeker’s U.S. Team looks to retain the Cup against Geoff Ogilvy’s International Team at Medinah Country Club, during the PGA Tour’s premier global event.

Learn More →

Meadows Fest

September 25–27 | Times Vary | Rolling Meadows, City of Rolling Meadows (3286 Kirchoff Rd)

Celebrate the best of Rolling Meadows at Meadows Fest! This three-day festival at Kimball Hill Park features tribute bands, local brews, delicious food, family activities, market vendors, a beer tent, the Taste of Rolling Meadows, and the annual Duck Race. Bring the whole family for a weekend packed with music, entertainment, and community fun.

Learn More →

Johnny Appleseed Festival

September 25–26 | Times Vary | Crystal Lake, Downtown Crystal Lake

The tradition continues with the 33rd annual Johnny Appleseed Festival in Downtown Crystal Lake! This all-day event brings families and the community together to kick off the fall season and all of its delights.

Learn More →

Cantigny Fall Fest

September 19–20 | 10:00 AM – 4:00 PM | Wheaton, Cantigny (1S151 Winfield Rd)

This family-friendly weekend features a vibrant market, live music, guided garden tours, and a variety of food trucks offering tasty bites. Kids can enjoy hands-on crafts, bounce houses, and a delightful petting zoo, creating memories for all ages.

Learn More →

Northbrook Shermerfest

September 27 | 12:00 PM – 4:00 PM | Northbrook, Village Green Park (Corner of Sherman and Meadow Road)

The Northbrook Historical Society cordially invites you to the 48th Annual Shermerfest in the Village Green Park and inside the Northbrook History Museum, located at 1776 Walters Ave. Food and fun for all ages! Enjoy the “Classic Northbrook” CARavan and Car Show through the streets of Northbrook and on the Village Green.

Learn More →

Sounds of Summer – The Petty Kings

September 27 | 4:00 PM – 5:30 PM | Wilmette, Hibbard Park (3000 Glenview Rd)

Bring a lawn chair and enjoy ‘The Petty Kings’ before the Sound of Summer series winds down for the season!