Uncover the dramatic stories, world-renowned architecture, and famous cinematic backdrops of the Windy City on an unforgettable Chicago highlights tour. Perfect for first-time visitors and history buffs alike, this experience takes you past the city's most legendary streets while making dedicated stops at its most celebrated landmarks.
Your journey begins at the historic Palmer House, a grand hotel built as an extravagant 1871 engagement gift, and the famous birthplace of the chocolate brownie. From there, head to The Rookery, one of the world’s very first skyscrapers, where you’ll step off the bus to admire its stunning Frank Lloyd Wright-designed lobby (a famous screen setting for Home Alone 2 and The Untouchables) and catch a close-up angle of the massive Willis Tower.
As you ride, take in views of the Chicago Board of Trade, the Federal Courthouse, and the striking Bowman and Spearman statues before stopping at Buckingham Fountain, a dramatic masterpiece three times the size of its Versailles inspiration. Continue down DuSable Lake Shore Drive past the Field Museum to Museum Campus, where you’ll step out for the absolute best panoramic skyline view in the city.
No trip to Chicago is complete without visiting Millennium Park. Pause to capture memories at The Bean, take in the architecture of the Jay Pritzker Pavilion, and marvel at the Crown Fountain. Next, step out above the Chicago River along Wacker Drive for unbeatable views of the Wrigley Building and Tribune Tower.
Finish your tour by cruising past the luxury shopping district of The Magnificent Mile and the historic Gold Coast, home to the original Playboy Mansion and 19th-century brownstones. From there, continue into Lincoln Park, passing its famous zoo, lush gardens, and historic sculptures, and pause at the Fullerton Street Bridge Overlook for an incredible skyline view before concluding along the glittering shores of Lake Michigan.
Please note, tour stops and routes may vary due to street closures. On Sundays, visits to The Rookery are exterior-only because the lobby is closed.