Crowd Work Wednesday is an interactive stand-up comedy show happening on March 25 from 7–8:30 PM at The Comedy Bar in River North. Hosted by Pat Bolduc & John Gasper, the show features a rotating lineup of comedians who skip the scripted material and instead riff directly with the audience—making every performance completely unique and unpredictable.

The Chinatown Lunar New Year Parade in Chicago takes place on Sunday, March 1, 2026, at 1:00 PM in the city’s Chinatown neighborhood. The parade begins at 24th Street and Wentworth Avenue and travels north along Wentworth toward Cermak Road . The event is free and open to the public, drawing thousands of spectators each year.

Chicago’s bar scene is gearing up for St. Patrick’s Day as WAMI LIVE hosts its annual Lucky Charms Bar Crawl on Saturday, March 14. The event spans multiple neighborhoods, offering entry to bars, drink specials, DJs, and themed swag.

Location: St. George Greek Orthodox Church, 2701 N. Sheffield Ave., Chicago

Sueños Music Festival 2025 takes place May 24–25 in Chicago's Grant Park, featuring Latin music stars like Shakira, Don Omar, Peso Pluma, and Grupo Frontera across two stages. With over 30 artists, expanded festival grounds, and ticket options ranging from GA to VIP, it's one of the largest Latin music events in the U.S. Passes are nearly sold out and available on the official Sueños website.

ART on THE MART is the world’s largest permanent digital art projection, lighting up the 2.5-acre façade of Chicago’s THE MART with contemporary artwork. The Spring 2025 program runs Thursdays through Sundays, 8:30–9:00 PM, from April 25 to July 6, best viewed from the Chicago Riverwalk. Featuring immersive visuals and audio, it showcases works from both global and local artists.

Chicago Cabaret Week 2025 runs from May 9–18 and celebrates the city’s dynamic cabaret scene. The festival features over 95 performers at 17 venues across Chicago and the suburbs, showcasing blues, Broadway, burlesque, jazz, R\&B, French chanson, and world music. It’s a unique chance to experience Chicago’s rich musical and theatrical talent in intimate settings.

TITANIQUE: The Céline-Powered Parody Making Waves in Chicago! Now through July 13, climb aboard the ship of dreams as TITANIQUE rocks the Broadway Playhouse at Water Tower Place. This wildly funny, award-winning musical reimagines Titanic through the power ballads of Céline Dion—who’s not just singing the soundtrack, she’s telling the story her way. It’s campy, heartfelt, and hilariously overboard. Don’t miss Chicago’s must-see musical voyage—now extended by popular demand!

EXPO CHICAGO is a leading international art fair held annually at Navy Pier, showcasing contemporary and modern art from over 170 galleries worldwide. The 2025 edition runs April 24–27 and features global exhibitors, talks, and public installations. Now owned by Frieze, the fair has cemented its status as a premier cultural event in Chicago.