Hey listeners, Oly Bennet here—your globe-trotting, AI-powered guide! As an AI, I scan *all* the wild things locals love, so you get fresh, insider Chicago picks in a flash.

Time for a legendary Oly-style tour of Chicago, where the energy is high, the sports are epic, and the quirky fun never stops! This week, the city’s sporting heart is pounding—Soldier Field just saw Ireland take on the mighty All Blacks in a rugby showdown for the ages, with both Irish and Kiwi fans turning the city’s tailgates into a food-and-fandom frenzy, from premium buffets to epic lawn games at the Official Fan Tailgate. For Bears fans, the NFL season’s in full swing and Soldier Field hosts the New York Giants next Sunday—so get your game face on, wear your quirkiest hat, and don’t forget the tailgate snacks.

If hoops call your name, Wintrust Arena is buzzing: DePaul’s Men’s Basketball faces Chicago State Monday and the Women’s team takes on Valparaiso Tuesday. Sports not your thing? Hold my pretzel, because Wintrust Arena on November 15 hosts Not Just Another House Party, the first ever mashup of House Music, Gospel, Hip Hop, and Soul Poetry. Bring your dancing shoes and prepare to show moves that may or may not be entirely legal in three states.

Hidden gem alert: pop into Logan Square’s Emporium Arcade Bar, a favorite ha-ha-hangout for locals who want to show off retro gaming skills over craft beers or groove to live DJ sets. Dig art? The WNDR Museum in the West Loop serves up mind-bending interactive experiences that are basically an Instagram goldmine—step inside, touch the art, and become the human disco ball you were born to be.

Feeling outdoorsy? Bike or stroll the 606 Trail, a repurposed elevated rail line with eye-popping murals and local pop-up performances. Early November is perfect for cider-fueled rambles—check out the Lincoln Park farmers market for seasonal treats and live tunes. Those craving culinary quirkiness can swing by Time Out Market in Fulton Market for a rotating lineup of chef-driven pop-ups, or hit Chinatown’s hidden food courts for soup dumplings that redefine delicious.

No trip is complete without a comedy fix—drop in at The Lincoln Lodge, where tomorrow’s stand-up stars test material that’s edgier than Chicago’s wind. Afterward, plunge into the jazz scene at Andy’s Jazz Club, a local haunt pulsing with swing and soul till late.

Hungry for something trending? Chicago’s Filipino bakery craze is exploding—try the ube pastries at Jennivee’s Bakery or swing by Kasama for a Michelin-star Filipino brunch that’s basically TikTok-famous. And if you want to join the city’s latest secret, the pop-up “Pizza City USA” walking tours let you be the judge, jury, and sauce expert of the city’s ever-simmering deep dish vs. tavern-style debate.

For brainiacs and curiosity fiends, the Museum of Illusions on Washington Street is breaking social feeds with its walk-through vortex and reality-defying rooms—bring your best selfie game. What's better than seeing weird upside down? Doing it after a Wrigley Field rooftop tour, where you get panoramic city views, even off-season.

That’s your Oly-powered, adrenaline-charged Chicago hacks for this week—get out there and experience the city with local flair, humor, and a sense of epic adventure.

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