By day, Chicago’s South Loop is all sleek apartments and sunshine — but after dark, the ghosts and gangsters of the Roaring Twenties come out to play. This original, top-rated walking tour takes you behind the glitter to the city’s wildest chapter, and it’s deliciously spooky.
A historian guide leads you through the streets that were once Chicago’s notorious vice district: underground speakeasies, secret tunnels, bootleggers and the gangsters who caused havoc in the 1920s and 30s. You’ll stand where notorious figures made their mark, hear true stories of the city’s bloody past, and learn why some spirits are said to still haunt these blocks. It’s part history lesson, part ghost story, all fun — guests consistently rate it a highlight of their Chicago trip.
It’s a walking tour through the South Loop, easy-paced and full of atmosphere, led by a guide who knows every mystery hidden behind every corner. The evening timing makes the stories hit even harder. Tickets start from around $38 per person — a fantastic value for such a unique night out.
Ready for a thrilling night in Chicago? Book this tour on Viator
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Photo: Viator
