After building a reputation for blending alternative comedy, spirited competition, and cannabis culture into one uniquely interactive experience, HighQ: America’s Favorite Drug Test is launching a new weekly comedy & variety showcase in Chicago: HighQ Hangout.

CHICAGO — Insider773 is bringing together wine lovers and house music fans this summer with the debut of " Catch a Vine ," a wine and house music pop-up taking place on Saturday , July 11 , at VIN312 Winery in Chicago's Ravenswood neighborhood.

Chicago Rum Fest returns to Chicago on April 25, 2026 , bringing rum enthusiasts, industry professionals, and curious newcomers together for a full-day celebration of rum culture at Logan Square Auditorium.

Chicago audiences looking for something different this spring can catch 420 Shakespeare , a comedy performance that blends classic Shakespeare with improvisation and unpredictable live theater at The Second City . The show runs inside the De Maat Theater at 230 W. North Ave., with select performances scheduled through May 2026.

The Evanston Folk Festival is officially returning to the North Shore on September 12–13, 2026, bringing a stacked lineup of nationally recognized folk artists to the lakefront. Headliners including Indigo Girls, Trampled by Turtles, Josh Ritter, and Valerie June are set to perform at Dawes Park in Evanston , offering one of the most curated and laid-back music experiences in the Chicago area.

CHICAGO — The wait is over. The official lineup for Lollapalooza 2026 has been released, and this year’s festival is shaping up to be one of the most diverse and high-energy editions yet. Set to return to Grant Park from July 30 through August 2 , the four-day festival will feature over 170 artists across eight stages, blending pop, hip-hop, indie, rock, and electronic music into one massive summer experience in the heart of Chicago. This year’s headliners are stacke d with global stars and fan favorites, including Charli XCX, Lorde, and Tate McRae, signaling a strong pop presence across the weekend. Chicago legends The Smashing Pumpkins will also take the stage, bringing a hometown moment that longtime fans will not want to miss.

Chicagoans looking to welcome spring with a burst of color can head to Navy Pier this Saturday, March 7, where the city will host its annual Holi celebration — one of the largest free festivals of its kind in the United States.

CHICAGO — Insider773 has announced a new partnership between its subscription platform, INSIDER+, and WAMI Tickets, giving new members access to a free ticket to the upcoming St. Patrick’s Day Lucky Charms Bar Crawl — a $20 value included with a $5 monthly subscription.

Chicago, IL — Insider773 has officially launched Insider+, a new $5-per-month subscription program designed to give members free or discounted access to events across Chicago and the surrounding suburbs.