Ways to Explore Chicago with Classmates Part 2: Winter Activities Guide

Ways to Explore Chicago with Classmates Part 2: Winter Activities Guide

Chicago has a temperate climate. “Summertime Chi” lives in infamy, trumping all other summertime and tropical destinations that have ever existed. With that comes the beauty and excitement of spring, balanced by the charm and nostalgia of autumn. While Chicago is filled with an abundance of joy and activities in the spring, summer, and fall, one season gets a bit of a bad rap. “Don’t go to Chicago in the winter,” “Ohh, the Windy City.” These are a couple of things you might hear when exploring your future MBA experience at Booth.

Like a true Chicagoan, I’ll be honest and tell you like it is (the cold has given us thick skin): winter isn’t my favorite season… but it ain’t all bad! Chicago winters can get old come March/April/May, but they are also wonderful for a plethora of reasons. While this chronicle is by no means exhaustive, it is meant to provide some inspiration for winter activities around Chicago and to paint a picture of what life can be like in the Windy City during the winter.


Want to embrace your inner main character? There isn’t much better than cozying up in a cute café with a cappuccino watching the world go by. Chicago has a vast selection of cafés dotting the city; this is a great way to explore Chicago’s neighborhoods and many Boothies would echo that this is actually an excellent way to set yourself up for a simultaneously relaxing and productive day. To get you started, check out Good Ambler in West Loop, Hexe in Roscoe Village, or The Wormhole in Wicker Park, but know that this riveting adventure could certainly become an endless pursuit. And who’s the cutie pie reading a book by the fire? That’s you!


Like many of Chicagoland’s offerings that I take for granite (pun) as a local, one of the area’s often overlooked (pun) amenities is the handful of ski hills we have close by! Wilmot, the smallest of the bunch (pun), is only about an hour north of the city; the further north you go, the larger the hills become. Past Wilmot, you’ll hit Alpine Valley, Cascade, and Devil’s Head, among others. Whether you want to try skiing for the first time before Ski Trip (Booth’s annual trek with 300 – 400 of your closest classmates), want to break the rust off before your inaugural trip out west, or are board (pun) and simply want to have a stellar day with some friends, run (pun) up to one of the nearby hills. Yes, Wisconsin isn’t Colorado, but like this paragraph, get yourself in the right mindset and you’ll have a ball (pun!). Who is the ski bunny sipping hot chocolate? That is you!


Most Boothies live just a stone’s throw, or a rock’s skip, from an unparalleled cluster of buildings in a park known as Museum Campus. You guessed it – Chicago has a world-class offering of museums, most picturesquely grouped in a scenic area along the lake. Among the most famous are the Field Museum, Art Institute, Shedd Aquarium, and Museum of Science and Industry; but that’s not it, Chicago has many more great museums and exhibits to discover whatever you are looking for. If you want to transport yourself out of the cold and into another world, waste away the entire day in any of Chicago’s incredible museums. Wait, it’s only been an hour?? But wow, look at that statuesque masterpiece. But that’s not a statue, that’s you!


If you’re like me, like a moth, you love lights. If you really want to enter the Christmas spirit, take a break from using your phone as a primarily light source, bundle up, and please go check out some of the incredible light exhibits illuminating Chicago. Most notably, Zoo Lights at Lincoln Park Zoo or Lightscape at the Chicago Botanic Gardens are totally lit! Both shows generally run from mid-November to early January each year. In Chicago fashion, these shows are over-the-top, completely immersive light displays taking place throughout the winter months. Stroll through Lincoln Park Zoo to take in the beautiful lights and the even more amazing animals, or head up to the Chicago suburbs to one of my favorite places in all of Chicagoland, the Chicago Botanic Garden for a light experience that will photosynthesize your soul. If you find yourself wanting more, venture to Brookfield Zoo for Holiday Magic, the City of Chicago Christmas Tree in Millennium Park, or Chicago’s Gold Coast for more residential light displays. What are those twinkling rays of light. They’re your eyes.


The most affordable ticket to Europe over the winter is a trip to Chicago’s Christkindlmarkets in Daley Plaza and Gallagher Way, taking place from November 19th – December 24th. Head there on your own, with a date, or some friends to drink mulled wine, eat authentic Bavarian treats, and grab some trinkets to decorate your miniature, fake Christmas tree. As someone who never celebrated Christmas but loves the holidays, Christkindlmarket totally gets me in the spirit. See that steamy, tall drink over there? That’s mulled wine – go get some!


Chicago, while having among the most robust restaurant offerings in the world, is also very much a meat and potatoes city. When the cold is setting in, my instinctual survival tactics kick in, and like a Chicago Bear, I go on a pursuit to consume all of the hearty food that graces Chicago. Consider this as official research coming out of The University of Chicago (Sample Size: 1, Author :Me) – food consumption should be inversely correlated with temperature; yes, wintertime is your perfect opportunity to indulge in all of the Chicago eats without the guilt and in the comfort of your puffy, warm parka. Additionally, many of Chicago’s restaurants and bars will have secret or not-so-secret Christmas pop-ups over the winter months, so you should absolutely go seek them out too. AS A PLUG, I plan to do a full Chicago restaurant overview – follow along to uncover your next Chicago dining destination for whatever cuisine/occasion you’re looking for. That juicy, stuffed porchetta spinning over the hearth – it’s me.


If you want to be a true Chicagoan, nothing says you’re from Chicago like not being in Chicago. There’s no way around it – our winter is long, and cold, and windy. I know this article has given you enough material to fill every day of both of your winters while at Booth, but when you need a break from hibernation or want to freeze your part-time residency at your favorite coffee shop, get out of town! I have to be honest: the highlight of my winters is travelling – going somewhere warm or skiing on a mountain with an elevation greater than 200ft. Chicago winters make travelling that much more enjoyable, and travelling makes coming home to Chiberia that much more Chiberable. If you couldn’t tell from the tone of this article, I may be a little stir crazy. But that’s ok because Spring Break is just around the corner, and Spring itself is only three months and 3-5 snowstorms away! What is that radiant specimen glistening in the sun? It is Chicago.

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