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Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

Step into Chicago’s coolest hidden bars on a mid-century cocktail adventure! Join a local guide to discover vintage lounges, secret speakeasies, and retro bars most tourists miss. Savor expertly crafted cocktails (own expense), hear untold stories of the city’s nightlife boom, and soak in stylish decor straight from the 1950s and 60s. This small-group tour is perfect for cocktail lovers, architecture buffs, and anyone seeking an off-the-beaten-path night out in the Windy City.

Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

1 hour 30 minutesFree Cancellation

Top Attractions in Chicago

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Entrance to Chicago Riverwalk surrounded by skyscrapers, Chicago

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Chicago Riverwalk

The Magnificent Mile in Chicago on a warm spring day.

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The Magnificent Mile

The statue of a lion at the entrance to Art Institute of Chicago, USA

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Art Institute of Chicago

A woman exploring the view from the Skydeck Chicago at Willis Tower.

Attractions

Skydeck Chicago at Willis Tower (Sears Tower)

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