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Finding "Warmth" in the Winter: Chicago's Winter Festivals

By Travel Savvy

Winters are Hot in Chicago!

Chicago winters are often associated with shorter days, colder nights, and a relentless attempt to stay warm. Although this may be true, don't let the Windy City's frigid temperatures keep you indoors and bring on seasonal blues! Travel Savvy has worked with locals to provide you with a list of Winter Festivals that can brighten up even the coldest and darkest of winter days! 

Randolph Street Market Festival 1

Photo Credit: Time Out Chicago

Randolph Street Market Festival

1340 W Washington Street

December 10th & 11th, 2016

10:00AM - 5:00PM

Every year pickers, collectors, and treasure hunters are in shopper's delight as they make their way through this European inspired indoor-outdoor market. With over 200 vendors, shoppers have the opportunity to buy anything from collectible furnishings to vintage clothing. Spend the day at your own leisure embracing the energetic holiday ambiance, shopping for antique holiday gifts, and enjoying the fancy food markets. 

Christkindlmarket 2

Photo Credit: @christmaschi Instagram


Daley Plaza

November 18 - December 24, 2016

Sunday - Thursday: 11:00AM - 8:00PM; Friday - Saturday: 11:00AM - 9:00PM 

Inspired by Christkindlmarket in Nuremberg, Germany which began in 1545, Christkindlmarket Chicago celebrates German and European tradition with its own local flare. Since 1996, visitors from all over the world travel to the Chicago loop to enjoy the region's largest open air Christmas festival. This magnificent outdoor market offers a unique shopping experience, with typical German Food and Drinks. A must try is the hot mulled wine in ceramic boots! As you walk along the glistening streets, you'll find incredible holiday entertainment, including live music and seasonal crafts. 

Sketch Fest 3

Photo Credit: Time Out Chicago

The Chicago Sketch Comedy Festival

Stage 773: 1225 W Belmont Ave

(773) 327-5252

January 5-15, 2017

Chicago locals know the best remedy for post holiday blues is the Chicago Sketchy Comedy Festival. This comic oasis has been providing the Chicago area with laughter and entertainment for 16 years and has become the largest Sketch Comedy Festival in the world, hosting over 180 groups from around the globe and performing nearly 200 shows in over 8 days. Join the 11,000 patrons who brave the wintery nights for original entertainment, and order your ticket to one of this year's 16th anniversary shows.   

Running of the Santas 4

Photo Credit: Running of the Santas

Chicago's Running of the Santas Pub Crawl

1206 N State St 

Check site for 2016 dates 

The Windy City's festive Pub Crawl is the perfect way for adults to celebrate the holiday season. The fun-filled night begins around 4pm at a local bar and continues as a "run" or drunk walk, to four other popular bars. Make sure to wear your best Santa outfit because the night ends with a North Pole party and Hottest Santa Contest. Tickets provide entry to the bars, entertainment, and drink specials! A portion of the proceeds from the Running of the Santas benefit the Leukemia Foundation and the That Others May Live Foundation. Be sure to check the site for this year's dates as December approaches. 


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