Embrace the crisp fall days with exciting activities that’ll make your autumn glow. From checking out charming boutiques to savoring pumpkin spice treats at seasonal festivals, there is so much to see and enjoy. Venture into fall foliage trails and local landmarks to infuse a dash of adventure into your autumn plans. Don’t miss out on these activities scheduled for this weekend to fully savor the changing leaves!
Laugh at the Bored Teachers Comedy Tour
The Bored Teachers Comedy Tour is a hilariously relatable journey into the lives of educators who have seen it all in the classroom. With quick-witted humor and uproarious anecdotes, this talented crew of educators-turned-comedians takes audiences through the trials and tribulations of teaching. Laughter is the best medicine for surviving the often absurd and hilarious world of education!
Date: September 23
Time: 7:30PM
Cost: $30+
Location: North Shore Center of Performing Arts, 9501 Skokie Blvd, Skokie
More info: northshorecenter.org
Prost to Oktoberfest
Head to Evanston for the Oktoberfest & Temperance Beer 10-Year Anniversary Party, where the fusion of German tradition meets a decade of local craft beer excellence. With their finest brews on tap, this celebration promises to delight beer lovers as they Prost to ten years of great libations!
Date: September 22
Time: 12-10PM
Cost: Free
Location: Temperance Beer Co, 2000 Dempster St, Evanston
More info: temperance.beer
Fall in Love with Autumn at Fall Fest
The Winnetka Park District’s Fall Fest offers something for everyone from pumpkin decorating and hayrides to live music and delicious seasonal treats. With the crisp breeze rustling through the trees and a warm sense of community in the air, it’s a perfect opportunity to embrace the changing seasons and enjoy a fabulous fall time!
Date: September 23
Time: 4-7PM
Cost: $20+
Location: Skokie Playfield, 600 Hibbard Rd, Winnetka
More info: winpark.org
Get Jazz-y at Hyde Park Jazz Fest
The Hyde Park Jazz Fest is a celebration of music and culture, that brings together world-class jazz artists and local talent for a weekend of soul-stirring performances. Beyond the music, attendees can enjoy delicious local cuisine, explore artisanal crafts, and revel in the atmosphere that makes Hyde Park Jazz Fest an early fall highlight.
Date: September 23-24
Time: Sat 1PM-12AM, Sun 1PM-7PM
Cost: Free
Location: Hyde Park, Woodlawn Ave and Midway Plaisance
More info: starevents.com
Celebrate the City with Chicago Live!
The Chicago Live! Show at Navy Pier is a spectacle that captures the energy of the Windy City like nothing else. From world-class musicians and talented performers to amazing visual displays, the show weaves together a narrative that pays homage to the city’s diverse heritage. Audiences are treated to a breathtaking journey through the heart of Chicago, leaving them with a deep appreciation for the city’s enduring charm.
Date: September 23-24
Time: Sat 12-9PM, Sun 12-6PM
Cost: Free
Location: Navy Pier, 600 E Grand Ave
More info: navypier.org
The 312 Block Party is Back at Goose Island
Named after the city’s iconic area code, the 312 Block Party transforms city streets with music, food, and artistry. Featuring an eclectic lineup of local and nationally acclaimed musicians, culinary delights from the city’s renowned food scene, and an array of visual and interactive displays, the 312 Block Party promises fun for everyone in your group.
Date: September 22-23
Time: Fri 5-10PM, Sat 4-10PM
Cost: Free
Location: Goose Island Brewery, 1800 W Fulton St
More info: gooseisland.com
See the Magic of the Water Lantern Festival
The Water Lantern Festival is a magical gathering that lights up the night with hope and unity. Participants gather by the water’s edge in Humboldt Park with a lantern that can be personalized with a message. Beyond the mesmerizing visuals, this festival fosters a sense of connection as attendees celebrate life’s special moments, both big and small.
Date: September 23
Time: 4-8PM
Cost: $23+
Location: Humboldt Park, 1400 N Humboldt Dr
More info: waterlanternfestival.com
Bon Appetit at Chicago Gourmet
Chicago Gourmet 2023 is the premier food and wine festival in our city where top chefs, sommeliers, and artisans converge to showcase their culinary artistry. From gourmet tastings and expert wine pairings to engaging cooking demonstrations and immersive food experiences, this event offers a journey through the world of food and drink across the city. Whether you’re a dedicated foodie or a casual enthusiast, this event is not-to-be-missed!
Date: September 22-24
Time: Varies by Event
Cost: $70+
Location: Various Locations in Downtown Chicago
More info: chicagogourmet.org
