The Windy City: Top Things You Can’t Miss in Chicago

21. The Secret Basement of the Green Mill Cocktail Lounge

Chicago is no stranger to speakeasies, but few can match the storied past of the Green Mill Cocktail Lounge. This legendary jazz club has been around for over a century, and its connection to the city’s gangster past makes it one of the most intriguing spots in town. Stepping inside feels like stepping back in time—with its dim lighting, vintage decor, and an air of mystery still lingering from the Roaring ‘20s.During Prohibition, this was one of Al Capone’s favorite hangouts, and the Green Mill had more than just great cocktails and live jazz—it had an elaborate escape system. Hidden beneath the club are secret tunnels, once used by Capone and his associates to evade the police during surprise raids. The tunnels connected to nearby businesses and even extended toward the lake, allowing gangsters to slip away unnoticed. While the tunnels themselves are off-limits to the public today, knowing their history adds to the atmosphere of the club.Today, the Green Mill remains a cultural treasure and one of the best jazz clubs in the country. Live performances keep the spirit of classic Chicago jazz alive, featuring incredible musicians playing everything from sultry blues to upbeat swing. Whether you're here for the history, the music, or the unbeatable ambiance, the Green Mill is an experience like no other. Grab a cocktail, sink into a velvet booth, and imagine the whispered deals and secret getaways that once took place just beneath your feet.