Top Chicago Active & Outdoor Classes

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.

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.