29th Taste of Randolph Street Fest Announces 2026 Line-up of Live Entertainment + Food & Beverage

The West Loop Community Organization (WLCO), along with Duff Entertainment, has announced the 29th-annual Taste of Randolph™ street festival, kicking off in Chicago’s West loop neighborhood, Friday, June 19th through Sunday, June 21st. The long-standing street festival, taking place on Chicago’s Restaurant Row, will feature some of the city’s cuisine, in addition to live entertainment, interactive community events, a full street dedicated to a kids’ zone, community raffle and much more.

“WLCO is excited to bring Taste of Randolph™ back for its 29th year of celebrating the West Loop community and everything it has to offer – some of Chicago’s best food and drinks, globally recognized live entertainment, and much, much more,” says West Loop Community Organization president, Julie Darling. “Each year, our goal is pack as much fun into six-city blocks as possible, and this year is no different. This year we’re introducing raffles into the mix this year, giving attendees the opportunity to win some incredible cash and prizes, including a 50/50 raffle, a silent auction, tickets to House of Blues and Lookingglass Theater Company, top-tier spa services, a variety of gift cards! We hope attendees are just as excited as we are with this new addition to the festival, which supports local businesses, while also giving festival goers the opportunity to win some exceptional prizes.”

At the helm of the street festival is food and drinks from some of the city’s restaurants and bars, like Alhambra, Blue Agave, Carbon, Cone, Gibson’s, Goddess & Grocer, Guttenberg, Haymarket’s Vienna Hot Dog Stand (supporting the rehabilitation efforts of the Haymarket Center), Hide & Seek, Kama, Nia & Jubilee Juice, Nicholas High Quality Meats (an old school favorite), Gangham Market, Stroop Daddy, and Pitaki, to name a few. As in year’s past, the event will implement an optional cashless purchase system, with vendors accepting all major debit and credit cards for food, drink, and merchant transactions.

“We’ve poured our hearts and souls into curating a fun-for-all event that Chicagoland residents and visitors alike can be proud of, and we hope attendees to this year’s fest see and feel all of the hard work that WLCO and Duff Entertainment have put into the 29th year of this cornerstone street festival,” states Darling.

Taste of Randolph™ 2026 will take place on six full blocks from, Randolph Street, between Peoria, Sangamon and Racine, rain or shine, unless severe weather conditions warrant the event to pause or close for a day. To learn more about the 29th-Annual Taste of Randolph™, including a full list of entertainment, merchants and food and beverage vendors, please visit: www.tasteofrandolph.org.