(Photo by Scott Olson/Getty Images)

(Photo by Scott Olson/Getty Images)

Whether you’re visiting from afar or are an ex-urb, Chicago offers a sled-full of reasons to visit during your Winter Break. The Midwestern burg boasts The 2015 TripAdvisor Traveler’s Choice Award for the top hotel in the U.S. (The Langham Chicago —and its spa is the only spa in Chicago to garner a five-star rating from Forbes Travel Guide) and Condé Nast Traveler named Chicago one of the best shopping cities in the world. Plus, Chicago can’t even carry all the recognition it gets for gay travel, dining, walkability, art, bars, museums and architecture. Better yet? It’s all probably cheaper in the winter!
Chi-Town Rising
Chicago River between Michigan Avenue and Columbus Drive
Chicago, IL 60611

Organizers promise an epic New Year’s Eve celebration in an effort to rival New York and Vegas on the last night of the year. Presented by Corona Extra and hosted by Hyatt Gold Passport, the privately-funded festival will be televised and feature well- known musical acts on a number of stages located on each side of the Chicago River, followed by an exciting countdown to 2016 at the huge Hyatt Regency Chicago, a Chicago star inching toward the sky and fireworks.

Sketch Comedy Festival
1225 W. Belmont Ave
Chicago, IL 60657
(773) 327-5252

Every January since 2002, the city has celebrated its comedic roots with the Sketch Comedy Festival, the largest sketch comedy festival in the nation. From Jan. 7-17, see original scripted material on stage, as well as sketch comedy experts talk about the form in various panel discussions. Tickets are only $15 to see national and international comedy groups in reunion performances, as well as brand new shows. 

Chicago Restaurant Week

Trip Advisor declared Chicago the number one pizza city in the country — the Food Network says we have the best burger in America, and 59 Chicago restaurants snagged approval by Michelin for its 2015 guide. Yeah, we got the goods, but why pay full price? Visit eateries on your must-eat list during Chicago Restaurant Week and enjoy special prix fixe menus starting at $22 for lunch and $33 and/or $44 for dinner (excluding beverages, tax and gratuity). From Jan. 22 to Feb. 4, 2016, more than 250 restaurants will be satisfying your kim chee taco, bacon cheeseburger, ramen, cowboy steak, fried chicken and duck l’orange hankerings at a great price.

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Tomorrow Never Knows
Lincoln Hall
3159 N. Southport
Chicago, IL 60657
(773) 525-2508

Adversity makes smart people resourceful, and ergo, the Tomorrow Never Knows festival held at Lincoln Hall and Schubas takes the bleak month of January in Chicago and tosses in well-regarded and emerging local and national independent acts to lift locals and visitors out of the deep freeze. Although too soon to tell what aural treats await Jan. 13-17, 2016, know that artists featured during the previous incarnations of the festival include Bon Iver, The Walkmen, Wild Belle, Cloud Nothings, Twin Shadow, Neon Indian, Little Dragon, Betty Who and Atlas Sound.

Chicago Theater Week
Various venues

From Feb. 11-21, 2016, you can choose from over 100 productions at very affordable prices ($15 or $30) during Chicago Theater Week. Tickets go on sale Jan. 5, 2016, so peruse the sched and choose your faves ASAP. More than 115 productions participated in 2015, including venues throughout the city and suburbs. Live theater fans can experience musicals, comedies, dramas and family-oriented theatre.

Related: Best Hotels For Business Trips To Chicago

Jacky Runice has been a columnist with the Daily Herald Chicago since grunge music and flannel was the new black. Her fingers and gray matter have been busy as travel editor of Reunions Magazine; penning a column that was syndicated around the nation via Tribune Media Services. Her work can be found at Examiner.com.