You’ll love this tour if... You’ve always been fascinated by the mystique of Prohibition, the drama of mob history, and the allure of Chicago’s big-city energy. You enjoy good food, fascinating stories, and a mix of history and culture in a lively, small-group setting!

Day 1 - Adventure awaits!

Your adventure begins with your departure and travel towards the Windy City! Upon arrival, settle into the historic Knickerbocker Hotel, an elegant landmark dating back to the 1920s that was once frequented by Chicago's notorious mobsters. This evening, step into Chicago's Prohibition past with dinner at the legendary Harry Caray's Steakhouse, located in a building once owned by Al Capone's trusted enforcer, Frank Nitti. Then, venture through a hidden bookcase into Nitti's Speakeasy, a recreated 1920s hideout where authentic décor, fascinating stories, and vintage cocktails transport you back to the Roaring Twenties. (L, D)

Day 2– Gangsters, Great Food, & Chicago by Water

Discover Chicago's colorful past on a guided Gangster & Food Tour, where you'll hear fascinating tales of Prohibition-era mobsters while sampling some of the city's most iconic flavors along the way. This afternoon, relax aboard Chicago's world-famous Architecture River Cruise as expert guides showcase the city's remarkable skyline and architectural masterpieces from the best seat in town. After the cruise, enjoy free time at lively Navy Pier to browse the shops, ride the Centennial Wheel, or simply take in the beautiful views of Lake Michigan before gathering with the group for dinner. (B, L, D)

Day 3 - Baseball, Shopping & Gangster Legends

Start the day with a behind-the-scenes tour of historic Wrigley Field,. Next, stop for photos at "The Bean" before enjoying free time along Michigan Avenue's famed Magnificent Mile. Whether you're shopping world-class boutiques, admiring historic architecture, or relaxing at a sidewalk café, there's something for everyone. This evening, enjoy dinner at The Village, one of Chicago's oldest Italian restaurants. Rich in tradition and famous for its connections to Chicago's colorful past, The Village offers the perfect setting to reflect on another memorable day in the city. (B, L, D)

Day 4 - The Getaway: It’s Getting Hot in the City

Following breakfast, we leave Chicago behind and make our way to historic Dubuque, Iowa, where another chapter of mob history awaits. Visit the elegant Hotel Julien, once a favorite refuge for Al Capone whenever the pressure mounted in Chicago. Tour the beautifully restored Al Capone Suite and learn the fascinating stories behind one of America's most infamous gangsters. After enjoying lunch at the historic hotel, sit back, relax, and enjoy the ride home as we share stories, laughter, and favorite memories from this unforgettable journey through Chicago's history, architecture, and legendary underworld. (B, L)