The best October 2024 events in Chicago

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

As if you needed an excuse to spend golden hour at Time Out Market Chicago's rooftop bar—we're hosting a very special happy hour until the cold snap arrives. Sip on vibrant spritz drink specials crafted for summer lounging, complete with a live DJ spinning feel-good vibes all evening long. Whether you're here to dance, chill or just toast to the moment, this is your chance to savor the season.

Learn how to make your own traditional maki rolls with an interactive class at Sunda. Expert chefs will guide you through the process of assembling temaki (hand-rolled sushi), futomaki (fat-rolled sushi) and uramaki (inside-out rolled sushi) using seaweed wraps, rice, spicy tuna and more. Classes are available at the Fulton Market and River North locations.    

Port Wine Fest returns to West Loop's Walden to celebrate the food, wine and culture of Portugal—one sip and bite at a time. Ticket holders will have the opportunity to sample a bevy of wines—white, red, sparkling and Port varietals—from 44 Portuguese producers and meet the winemakers behind the vino. Rounding out the experience, acclaimed bakery Cadinho will present thoughtful gourmet pairings to transport you straight to Portugal.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

Get in the holiday spirit at this annual ghoulish makeover of the Chicago Botanic Garden. The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit creations and staged along the garden's pathway where other entertaining characters and activations await visitors. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

Activating cultural centers across Chicagoland, JOURNEY Chicago is a monthlong event series designed to foster community and communication between cultures. Organized by several members of the Chicago Cultural Alliance, JOURNEY Chicago weaves together music, art, storytelling, dance and food programming into a month’s worth of low-cost or free events. This year’s event calendar includes a performance about “Reiki, and Haitian & African-American Practices;” a “Zoo Fiesta,” a genealogy-focused “Family Album Day” and more.

Fall is about more than crisp leaves and pumpkin spice—and Island Party Hut is here to prove it. The Riverwalk tiki bar’s fall fest returns with seasonal cocktails, river hayrides, a pumpkin patch and more. With live music, photo ops and a drink included in your ticket, it’s a celebration guaranteed to get you in the autumn spirit.