—The Chicago Trolley & Double Decker Holiday Lights Tour (ChicagoTrolley.com): Sure, it’s a little schmaltzy to some, but others find this tour—a two-and-a-half-hour event that brings riders to two of Chicago’s best-loved holiday attractions, including the Christkindlmarket at Daley Plaza and ZooLights at Lincoln Park Zoo—to be pretty cool. It will take place at held at 5:30, 6 and 6:30 p.m. Nov. 30-Dec. 2 and Dec. 7-23. (BTW, the tour is marking its 25th anniversary this year.)
—Skydeck at Willis Tower (theskydeck.com/): The prospect of stepping outside the tallest building in the Western Hemisphere (1,353 feet) can be daunting to almost anyone—but the reward is definitely worth it. But you can do more than see four states (Illinois, Indiana, Wisconsin and Michigan) and strike cool poses on the ledges: There’s the Pie in the Sky dinner experience, complete with pizza, and Selfies with Santa on Dec. 20-23, 12-5 p.m.
—Glamping at Raised (RaisedBarChicago.com/events.html): This past summer, The Gwen offered an extravagant glamping experience. Now, Raised, an Urban Rooftop Bar (at the Renaissance Hotel at 1 W. Wacker Dr.), is inviting both Chicago residents and visitors to check out a cheaper (but no less fun) option. For the entire winter, this rooftop destination is decking out its outdoor area with lush blankets, pillows, trees and greenery to bring an urban glamping experience. Additionally, Raised will be offering a special menu of winterized food and beverage items for guests to enjoy. Be sure to check out the hot toddies!
—Chicago Gay Men’s Chorus (CGMC.org): The acclaimed group is marking its 35th anniversary Nov. 30-Dec. 2 with a series of concerts at different Chicagoland venues. In addition, there will be collaborations with About Face Theatre, Allegrezza, Artemis Singers, Chicago Pride Guard, Chicago Spirit Brigade, Chicago Tap Theatre, GayCo, Lakeside Pride Music Ensembles, Lakeview Orchestra, Pride Films & Plays, and Windy City Gay Chorus.