Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of train travel with the magic of California's breathtaking scenery. From... More

Step aboard the iconic Cap Streeter for an unforgettable evening cruise departing from Navy Pier. Shoreline’s Special Event Series combines curated local beverage tastings, delicious light bites, music, and breathtaking skyline ... More

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the cityâ€... More

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Wi... More

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians w... More

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transforming each stretch of road int... More

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous past as you explore the sites connected to America’s most notori... More

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages prevails. This tour includes a beautiful drive through the Midwest and a sc... More

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insig... More

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With com... More

Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this time-saving, architecture-focused cruise. See the city's most important buildings all on one tour—including the Willis (Sears)... More

Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embraces a serene atmosphere where horse-drawn carriages navigate past Victor... More

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Wind... More

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, whe... More

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist ... More

Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpicked points of interest. Explore iconic landmarks, historic towns, scenic detours, hidden gems, c... More