The best things to do in Chicago today

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

Step aboard City Cruises’ Seadog for a fun-filled journey through Chicago's history of ghosts, spirits, scandals and sins. As guests cruise along the Chicago River for 45 spooky minutes, expert—and costumed—docents weave stories of Chicago's darker side while cruising through the city's most iconic architecture. The cruise is BYOB, so be sure to bring a bevvy of your choice. 

A terrifying story set in the world of the Paranormal Activity film franchise, Felix Barrett (Sleep No More) and Chicago playwright Levi Holloway's latest endeavor promises chills and thrills. Here's what you need to know: James and Lou flee from Chicago to London in hopes of escaping the past, but they soon discover that it's not the city that was haunted—it's them. Chicago will be the first city to experience the highly anticipated play, which will head to LA, San Francisco and Washington, D.C. later this season. 

Spooky season will get a bit boozier this year thanks to this horror-themed cocktail pop-up at the Albion Manor, where Halloween lovers can sip expertly mixed cocktails amid metal music and goth decor. Drinks are imbued with playful touches and include choices like Corpse Flower (tequila blanco, ube, Giffard Banane, lime, sherry) and Griselda’s Revenge (gin, vermouth, tarragon, thai spice). Want to recreate the creepy vibe at home? Several of the drinks are served in Halloween glassware that’s available for purchase onsite.  

Experimental Sound Studio's longtime partnership with the Chicago Park District and Lincoln Park Conservatory continues with “Semblance of Fern,” a new sound installation by composer Sarah Belle Reid. The immersive installation explores the formal connections between mathematical models and nature in the contemplative confines of the conservatory's Fern Room. After getting your fill of tropical palms and vibrant flowers, mosey over to the Alfred Caldwell Lily Pool, which is free to visit and recently reopened to the public.

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world. Not sure where to start? Check out our first-timer's guide to the exhibition. Stay up-to-date by visiting the Chicago Architecture Biennial website.

Round up your family for a wild, multi-weekend Halloween festival perfect for all ages to enjoy. Decorate a pumpkin, take a spin on the decked-out carousel or pose for photos amongst giant inflatables and wooden cut-outs of Halloween characters. The not-too-spooky event also treats some of the zoo's animals—including capybaras, polar bears and gorilla—to pumpkins that they can play with, nibble on and smash. 

This annual celebration of scary films returns to the Music Box Theatre for a monthlong marathon of frightening, thrilling and chilling movies. Catch screenings of films like Addams Family Values, Let The Right One In, Bride of Frankenstein and many others. Notice some holes in the schedule? More films are yet-to-be-announced, and they're sure to be some doozies. You can see a full lineup here. 

Founding frontman of the Talking Heads—and musical legend in his own right—David Byrne is returning to Chicago for a four-night stand with a new album in tow. Byrne’s forthcoming album, Who Is the Sky?, is his first release since 2018’s universally acclaimed album-turned-Broadway-show-turned-concert-film American Utopia. To celebrate the release of Who Is the Sky?, Byrne will travel around the globe with a band comprised of 13 musicians, singers, and dancers—all of whom will be mobile throughout the set.

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

Make your Halloween a little BOO-zier (get it?) during the Ravenswood Costume Crawl, which invites costumed attendees to stroll along a route stocked with local desserts, snacks and drinks samples on Montrose and Ravenswood Avenues. Come dressed to impress—one lucky person will also win a bottle of Malört.

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing.  When is Jack's Pumpkin Pop-up? The pop-up opens September 18 and runs through November 2. How do I get tickets to Jack's Pumpkin Pop-up? Timed-entry tickets can be purchased via Jack's website. Prices vary based on time and ticket type.

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.

“Take Care with Peanuts: The Exhibit” is an immersive fan experience inspired by a global initiative of the same name. Based on the captivating world depicted in Charles M. Schulz’s iconic comic strip, the exhibit brings the beloved Peanuts gang to life through interactive displays and hands-on activities promoting self-care, empathy and environmental stewardship. The overarching hope governing “Take Care with Peanuts” is to inspire action and remind visitors to love themselves, their communities and the planet. 

A film buff yapping over a film can be the most annoying experience imaginable for a moviegoer—unless the person doing the talking is the director. Join Vimeo's curation team as they screen their favorite short films with live, unscripted commentary from some of the online video platform's most celebrated creators. The program will kick off with a commentary-free screening, followed by a second run-through featuring creator commentary. The screenings will be followed by a reception with complimentary drinks and snacks.

One of Chicago's most popular farmer's markets, Green City Market welcomes vendors selling regional produce to the south end of Lincoln Park (between Clark Street and Stockton Drive) on Wednesdays and Saturdays. Amid the rows of vendors, you’ll find farm-fresh eggs from Michigan, cheese from Wisconsin and scrumptious pies baked by Chicago’s own Hoosier Mama Pie Co.

The eighth annual Destinos: Chicago Latino Theater Festival returns to Chicago with a four-week lineup of live theater performances at venues throughout the city and Northwest Indiana. As usual, this year's lineup revolves around Latino-driven storylines, including several world premieres: Teatro Inovarte (a musical blending mariachi, ballet and queer love), Concrete Content (an immersive sketch show reimagining Latin futures via fake movie trailers) and more. You can view a full lineup of plays on the fest's website. 

For 39 years and counting, the National Museum of Mexican Art has celebrated one of Mexico’s most extraordinary traditions with a multimedia exhibition. This year, “Día de Muertos: A Celebration of Remembrance” is dedicated to the Texans and New Mexicans who tragically lost their lives in 2025's flash floods. After you've toured the exhibition, make your way to the museum's courtyard space, which will house an installation designed and curated by the youth artists of Yollocalli Arts Reach. End your visit with a moment at the community ofrenda—add a note, drawing or memory to honor someone you’ve lost and be part of this collective tribute. As usual, admission is free—anyone is welcome to stop by the museum and pay their respects to those who are no longer with us.