Welcome, you fabulous crew of adventure-seekers, to Things to Do in Chicago! It’s Friday, November 14, 2025, and right now, the Windy City’s buzzing with electric energy—the kind that has folks swapping scarves for selfie-sticks and plotting their next deep-dish encounter. If you just peeked out your window, you know it’s classic autumn—crisp, cool air, flashes of gold in the parks, windy enough to make you feel like you’re auditioning for Chicago’s next marathon. As for city happenings, today is the launchpad for epic events, wild stories, and maybe, just maybe, a taste of the world’s quirkiest competitions.

Kicking off tonight, Chicago’s Union Station transforms into a foodie wonderland for Culinary Care’s Gourmand Gala. More than 30 tasting tables will tempt you with bites from Michelin-starred restaurants and James Beard-winning chefs. Not just a fancy feast, this party fuels a great cause—meals for people fighting cancer. So if your idea of sportsmanship involves competitive snacking and rapid-fire fork action, this is your championship arena.

Feeling the need to wander? Bounce over to The Field Museum’s Eras After Dark: a proper 21+ bash that lets you mingle in themed lounges, sip quirky cocktails, and roam prehistoric halls after hours. This is where you can hunt dino facts instead of dinosaurs themselves, and maybe invent the first “Night at the Museum Olympics” involving mummies and meteorites.

If family festivities are your jam, tomorrow’s Lycée French Market is a must. A two-day extravaganza lands with more than 75 French and local artisans, a bistro loaded with pastry, live entertainment, and crowd-pleasing gift ideas. Pro tip: brush up on your best beret-wearing pose for all the Parisian selfie stations.

And for fitness fiends itching for a challenge, Navy Pier is roaring with HYROX this weekend. Think of it as the decathlon for mere mortals—row, run, sled-push, and high-five your way through the ultimate urban obstacle course, with the skyline egging you on at every turn.

If you’re wild about markets or your sport is competitive vintage shopping, Randolph Street Market Festival returns this weekend. Picture 125+ vendors hawking designer fashion, estate jewelry, home goods, and enough hot cocoa to keep your stamina up while you dodge elbows and track down the quirkiest finds.

On the concert circuit, Lincoln Hall hosts ROCHELLE JORDAN & Essosa for an electronic-fueled night, and the House of Blues lives up to its name with a blues showcase starting at 5 p.m.—prime time for truly epic toe-tapping.

Local news light: several restaurants are making grand appearances this month, with Chinatown’s walking tastings picking up steam and Hyde Park’s brunch scene booming with new Sunday specials. Heads up for commuters—the CTA is rolling out extra buses for festival weekends, especially near Navy Pier and Union Station, so plan ahead and avoid missing that championship pancake flip.

Now for my very own Oly Bennet tip—never underestimate the power of Chicago’s underground pedway! It’s like the city’s hidden obstacle course for locals, connecting downtown buildings with labyrinthine tunnels. Dodge the wind, explore downtown, and test your navigation skills. Legend has it, elite local “Pedway Pros” compete to see who can sprint from City Hall to Macy’s without ever coming up for air.

Before I dash off—get ready for tomorrow, when Hyde Park’s Holiday Handmade Artisan Bazaar opens for one day only: crafts, fashion, food, and cocktails come together in a maker’s paradise, plus look out for “Game Day at Ja’ Grill” with NCAA football and Caribbean brunch. Tune in for the next scoop on quirky competitions, wild Chicago discoveries, and the insider tips that make every day legendary.

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