Holiday Deals in Chicago

Description

Whether it's due to the wind, the fast talk, or the food, the Windy City isn't shaking its moniker any time soon. With this adventure, you can catch Second City at its breeziest and most delicious: a BYOB, ugly sweater trolley ride through Chicago's seasonal attractions and holiday landmarks. Don your ugliest festive threads and head to The Fireplace Inn, where our guides will be waiting to check us in. Here, we'll shoot the breeze while noshing on sliders and fries, and prep for our gawker ride through Chicagoland's yuletide lights. As soon as we board a vintage trolley from Chicago Trolley & Double Decker Co, we'll be whisked off toward Christkindlmarket, The Magnificent Mile, State Street and Macy's Holiday Windows, and Daley Plaza's 40-foot Tree. (Trips on weekends and Fridays also include a stop at ZooLights.) At each site, we'll hop off, pose with the decadently dressed models and event hosts, and snap our cameras at will. After soaking in the urban winter wonderland, we'll head back to Fireplace, where we'll show off our ugly sweaters and vote for the one wearing the most unappealing. A cash bar will fuel the reverence further, letting us catch wind of all the seasonal sparkles we just saw.