Welcome, globe-trotting thrill-seekers and Chicago daydreamers, to Things to do in Chicago with your guide Oly Bennet! Today’s date is Sunday, September 28, 2025, and the city’s got that crisp fall energy buzzing through the air. Sweater weather is in full swing—expect sunshine, perfect jacket temps, and golden leaves swirling down Michigan Avenue. Outside, Chicagoans are already fueling up with pumpkin lattes and plotting their festival attack plans, because this city never naps on a Sunday.

What’s the city vibe today? Absolutely electric. We’ve got a smorgasbord of happenings: art lovers, music buffs, families, vintage fans—you’re all covered. Let’s serve up a rapid-fire rundown of some standout events happening right now.

For the artsy crowd, you can’t miss the second day of the Randolph Street Market Festival. This West Loop favorite is a treasure hunter's heaven: vintage finds, vinyl, crafty makers, typewriter poets mingling with food trucks, and a live music lineup that’s basically a Chicago road trip for your ears. Highlights today include the Tony Morrison Jazz Quintet, Joe Wortell & the Natural Good Country Western Band (bring your cowboy boots, y’all), and rockabilly beats by Al Simon & the Saturn Kings. It all runs through late afternoon—bring cash and comfy shoes, and prepare to adopt a flamingo lamp or three.

Fancy some musical highbrow? Over at Epiphany Center for the Arts, at 2 pm, the internationally acclaimed pianist and composer Philip Daniel weaves together classical and cinematic soundscapes in an intimate concert—the man’s basically the soundtrack to your autumn daydreams. Stick around for 100% Bachata Sunday at 6 pm, where the dance floor welcomes everyone to sashay and sway through Chicago’s juiciest Latin grooves. It’s their first-ever Bachata night at Epiphany, so bring your best spins!

Bringing the family? The Lincoln Park Zoo Fall Fest has you covered, with free admission, pumpkin patches, hay mazes, and sweet treats—yes, toddlers on sugar highs are a legitimate sport at this event. It runs every Friday, Saturday, and Sunday through October, and it’s a staple if you want a dash of Halloween without the mayhem.

For the sustainability-minded, the Sustainability Market is in full swing, offering eco-friendly finds, swap shops, and local green initiatives—a gentle reminder that saving the planet can be stylish, and Chicago is always on-trend.

In cultural news, the CheckOut music and arts venue just completed its grand opening celebration—it’s a converted 7-Eleven now pouring adult slushies and fueling affordable culture all season. The city is abuzz over this quirky new hangout spot.

Transit tip: CTA’s Red Line maintenance wrapped early this morning, so trains are running smoothly—no grumpy morning commuters today, just high-fives for transportation miracles. And if you’re eyeing brunch, two new restaurants just flung their doors wide in Wicker Park—a French-Vietnamese fusion bistro and a Mediterranean-Japanese hybrid. Chicago is officially a passport with a skyline.

Classic must-dos: catch the shimmering lake views from the Chicago Riverwalk, grab a selfie with The Bean before the out-of-towners mob it, and if you haven’t swung by a speakeasy yet, make tonight the night to tuck behind a bookshelf for cocktails and jazz.

Local tip from Oly: If you’re gunning for Chicago-style hot dogs, remember—no ketchup, unless you want a stern talking-to and possibly a side-eye from a lifelong Sox fan. Seriously, the city council might write this into law.

Hot tease for tomorrow: Don’t miss Alice Sara Ott’s rare back-to-back performances of Ravel’s piano concertos, plus get your bid on at the Village Chicago’s “Many Voices, One Song” gala with Broadway hits blaring and prize raffles galore.

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