Artful Weekends in the Windy City - Oly's Guide to Epic Chicago Events

Welcome to Things to Do in Chicago! It’s Sunday, September 14, 2025, and your pal Oly Bennet is here, fresh off a plane from chasing cheese in Gloucestershire, ready to dive into the epic, electric vibe of Chicago today. Picture this: it’s a classic Windy City evening with a hint of fall crispness, a touch of lake breeze ruffling your hair, and a whole city primed for adventure like you’re about to set a world record in urban exploring.Let’s jump into the action! Today, Chicago’s bustling with events—there’s something for every mood, whether you’re hungry for culture, craving tunes, or just want to people-watch while munching on street food. For the art lovers, the Lakeview East Festival of the Arts is throwing its 20th annual party with 150 visual artists showing off everything from paintings to sculpture—it’s a visual circus, totally free and going on until 7 PM. Not far away, Ravenswood ArtWalk turns the industrial corridor into a bohemian wonderland, with galleries and live music—it’s like stumbling into a secret neighborhood festival where you might just meet a future Chicago legend.For my flavor fanatics and shoppers, the Maxwell Street Market and Glenwood Sunday Market are open and bustling. You’ll find everything from tamales to wild vintage finds—expect live music at Maxwell, produce at Glenwood, and real Chicago characters at both, until 2 or 3 PM.Family outings? The Peggy Notebaert Nature Museum has a Family Bird Walk around North Pond happening at 10 AM, and later, unleash your wild side making butterfly art or watching the first flight butterfly release. Head over to Parkway Bank Park in Rosemont for Fall Fest, running 1 to 5 PM, with carnival rides, music, and enough snacks to fuel even the most ambitious bouncy-house athlete.Live on the Lawn featuring Fernando Jones & Knott Us Band hits the Epiphany Center for the Arts at 4 PM—think blues, soul, and funky beats, all for free. And tonight, the Chicago Immigrant Orchestra returns with its world-spanning sound at 7 PM, celebrating Chicago’s global spirit with one phenomenal album release party. For the theater crowd, check out “Angels in America, Part Two: Perestroika” at Windy City Playhouse—because Chicago’s performing arts don’t just break ground, they build whole new stadiums.On the local news front, listen up foodies! There’s a buzz about new restaurant openings on Randolph Street—keep an eye out for eclectic menus and late-night bites. Transit-wise, the city’s rolling out extra express trains on the Blue Line for festival weekends, so hopping around is smoother than a Zamboni on ice.Must-do’s? Hop aboard a Big Bus Tours’ hop-on, hop-off ride to catch classic sights and hidden gems, from Millennium Park’s Franz West installations to the mysterious gardens of the Riverwalk. For sunset magic, stick around for ART on THE MART—imagine epic digital art projected on riverside buildings, free from 7 to 8 PM.Local tip from Oly’s playbook: If you can’t decide between deep-dish or Chicago-style hot dogs, hit up a local stand and ask for both—you’ll probably spark a passionate food debate with a stranger and maybe score free toppings. Plus, don’t miss murals in Pilsen, where every wall is a new sporting tale and a swoosh of spray paint.Tomorrow, get ready for Under the Picasso Noontimes at Daley Plaza, and the Museum of Contemporary Art has free admission for Illinois folks—legendary art and free entry, who says Mondays are dull? Stay tuned for more wild events, unusual competitions, and strange-but-true Chicago sports from Oly Bennet!Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI

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