The Windy City: Top Things You Can’t Miss in Chicago

17. Wrigley Field’s Hidden Speakeasy – The American Airlines 1914 Club

Wrigley Field is one of the most legendary ballparks in the country, but hidden beneath the iconic stadium is an exclusive speakeasy that takes baseball fandom to a whole new level. The American Airlines 1914 Club is an ultra-luxurious, Prohibition-style lounge that most fans don’t even know exists. Nestled right behind home plate, this elite underground retreat harkens back to baseball’s golden age, offering a sophisticated, intimate experience unlike any other. Entering the club feels like stepping into another era. The dimly lit atmosphere, plush leather seating, and vintage decor transport you straight to the 1920s, while the walls are adorned with rare memorabilia that tells the history of the Cubs and Wrigley Field. What makes this space truly special, however, is its all-inclusive perks—from gourmet dining and premium cocktails to a full selection of craft beer, fine wines, and spirits. The experience isn’t just about luxury, though—it’s also about exclusive access. Members of the 1914 Club get to skip the regular stadium lines, enter through a private underground entrance, and enjoy the best views in the house with seating just inches away from the field. While entry to this secret speakeasy requires a special ticket, just knowing it exists adds a whole new layer of excitement to a game day at Wrigley. If you’re lucky enough to snag a spot inside, you’re in for one of the most unforgettable baseball experiences Chicago has to offer.