Walking tours let you explore the very sidewalks where that city's famous denizens once strolled and yelled, "I'm famous and I will live forever!" at passing cars. Feel the history beneath your feet with this Groupon.
$25 for an Inside the Loop Walking Tour for Two (Up to $52 Value)
Over the course of two hours, an energetic guide leads groups on a half-mile course that winds through the streets and buildings of the Loop and parts of the indoors, underground Pedway. As they pass through the interiors of landmark stores, a chapel in a skyscraper, and the Chicago Cultural Center, among other highlights, visitors get added insight into the city’s history and inner workings through photos and video clips that the guide shares on iPads. Tours depart from Chase Tower at 10 a.m. Thursdays, 3 p.m. Fridays, and 1:30 p.m. Saturdays and Sundays. Children younger than 5 can attend for free.
Founder Amanda Scotese, an avid traveler and freelance writer for Rick Steves's renowned travel guides, delegates sure-footed guides to lead sightseers to iconic landmarks and down the back alleys and lesser-known nooks of the Windy City. Tours probe the ins and outs of the Chicago's neighborhoods, such as the Loop, where they fill eyes with the sights of world-renowned architecture and minds with the secrets of the Pedway, an underground walkway that connects buildings throughout the business district with the Ninja Turtles' lair. The Historic Chicago Bar Tour, born of Chicago Detours' desire to spread knowledge of the city's entertainment history, takes tour-goers to three historic bars in an exploration of how the city had fun. Private group Jazz, Blues & Beyond tours explore historic neighborhoods on the North and South sides, and include diversions such as harmonica lessons from a bona fide blues blower. Chicago Detours also offers private-group tours for birthdays, family reunions, and corporate team-building exercises. Private group tour options also include Meat History of Fulton Market and Chicago Neighborhoods and Cultural Diversity.