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What To Do in Chicago for The Holidays

by Maggie Suszka

Sweet home Chicago. The windy city where the pizza is deep, the winters are brutal, the folks are wholesome, the “aaa’s” are longer, and our sports teams are worth defending — and some would say, worth fighting for. I’m not one to hide any of my gushing love for the Chi, but I’m not the only one. Two of Chicago’s coolest neighborhoods have made the ranks in Hot Spot’s 25 Hottest Neighborhoods in America, Wicker Park and Logan Square.

So brace yourself for a love letter to my hometown as I show you a must-to-do list of Chicago’s best spots to check out during these colder months in the city – whether you’re taking a trip, meeting your S.O.’s family, going to your five-year high school reunion, visiting those relatives you haven’t seen in years, or if it’s your first trip ever. Scroll below to see where you can have a chill time in the Chi.

Igloos to Stay Chill Outdoors

The first is one I have yet to check out myself, but in one of the hottest up-and-coming areas in the city, which isn’t a neighborhood but the city’s Riverwalk. At the Riverwalk at Chicago City Winery, they currently have fabulous and fairytale-like igloos pitched in lieu of their regular tables and bar seating. So, if you find yourself wanting to get drunk in the chilling temps, City Winery is the place to head straight to, so you can spare yourself frostbite, but still get drunk. The only downside to these Narnia, otherworldly homes is that it’s a set price, so it could hurt if you’re balling on a budget. Check out the details to the igloos and how to reserve one here.

Hot Cocoa Hotline

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Yes, it is.♥️☕️📍

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If you’re looking for the best hot cocoa or your favorite latte to warm you up during your time sight-seeing in the River North Neighborhood, the place to go is Bodega Imports. Not to mention they have perfect (Instagram, kind of perfect) picture floors. And they’ll make some pretty chill art on your lattes – like Bruno Mars and Post Malone faces or an inscribe Chicago, like I requested during my last visit. Also, you can’t leave without something sweet – they have everything from adorning that cup of hot cocoa with doughnuts and other frills to full-blown Churro Sundaes.

Serious Winter Window Shopping

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#macyschicago #chicago

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During your sightseeing, it’s worth going to check out Macy’s holiday windows. Macy’s on State Street will put you in the holiday mood instantly. If it’s not below 0, you will find groups of tourists and people huddle around the beautiful windows. I learned that Macy’s have been wowing folks on the street with their windows since 1870. Macy’s was the very first store to feature holiday windows created for the pure joy of the season. Macy’s has a few other fun events for the season, including Santaland, their tree lighting, and tea in the beautifully decorated Walnut room (my personal, close to my heart favorite).

All of the Lights

Lincoln Park, a nightlife destination and more family-focused neighborhood in the city, (who thought those two could be in the same description of a neighborhood. Zoo Lights is where to have a romantic walk central park kind of style, where to bring the kiddos along, spend time with your best friends, or have a few drinks and run around the zoo a little tipsy admiring the lights and majestic animals. And even after the holidays are coming to a wrap and you’re looking for a place to celebrate the new year, you can spend it at Zoo Year’s Eve, where you can enjoy all the magic of zoo lights from carousel rides, ice sculpting games, along with some sweet tunes and cocktails all night long.

Art (for Art’s Sake)

The Lions, dubbed the “Guardian Lions” in front of the Art Institute of Chicago help pronounce when it’s finally “’tis the season” in Chicago. The tell-all holiday sign is when the guardian lions festively, and proudly, dawn their yearly wreaths around their necks. While the Art Institute of Chicago is a very exceptional source of art, culture and works new and old year-round, it’s a special place to visit during the holiday months.

Skating And The City

Looking to bust a move and get a winter friendly and fittingly festive workout on? Look no further than the fairly new ice-skating rink at Maggie Daley Park. The rink is one that is out of the ordinary, shaped like a winding ribbon – perfectly curving to the shape of the city’s skyline, providing unmatchable views and an unforgettable skating experience. The downside? Wait times to rent skates can be brutal, and the Zamboni takes upwards of an hour to clean up the ice due to the unique shape. But there are some fast passes available. If you arrive and find the line wrapping too far away to the far curve of the ribbon, there’s another rink a few blocks away at Millennium Park. But it’s an oval shape and probably just as crowded, so you might as well wait out the line – or try to catch the ribbon during an off time. Can you tell I’m biased?

Christkindl Market

The Christkindl Market in Chicago is in the heart of the city at Daley Plaza – a focal point for offices in the city, right off of State Street. If you’re looking to kill some time during the day, or in need of a cup of hot cocoa to warm up while out and about shopping or even a pick-me-up after-work look no further than the Christkindl Market. Any Chicagoan will tell you that the pop-up holiday village is an incredibly special tradition to the city. It is reminiscent of German and European tradition (with Chicago’s own local charm) and equipped with pop-up wooden home-like shops, selling festive high-quality goods from ornaments, home décor, clothes, handmade crafts and more. Not to mention the impossible to resist food vendors. My go-tos include roasted nuts, sweet cakes, and hot cocoa. If you can’t make it to the open air festival downtown, there’s another one in Wrigleyville — paired with an outdoor ice skating rink!

He Sees You When You’re Drinking 

Speaking of Wrigley, and the fact this list would not be complete without a drinking specific destination to send you off too, Santa Baby Bar is the *allegedly hottest* city’s pop-up bar of the season. It’s completely covered in Christmas decor, has multiple bars for whichever holiday mood you’re in — whether you want to *chill* in the beer hall of the Alpine Village, get whimsical in the Winter Wonderland, tell Santa what you really want this year in his workshop, bust a move with DJ SC or hit the “diver bar” — Rudolph’s with all the other drunk elves. Plus, don’t forget about the festive drinks! They’re offering specialty drinks, ranging from The Clausmopolitan, Jingle Juice, the Elf Fashioned, to the Rum Bull Rudolph and more.

Tea For Two

If you’re not a member at Soho House, don’t fret. You’re still invited to tea, at The Allis. Below the Soho House in Chicago (located in the up and coming West Loop neighborhood), is a warm and welcoming social space – a perfect escape from the frigid Chicago air. While afternoon tea seems fitting for a reunion or to catch up with a special someone whether it’s a friend or family, they also serve breakfast, lunch dinner and of course, happy hour! There’s Live Music every Tuesday from 6 pm to 9 pm and Happy Hour is Monday through Thursday, 3 pm to 6 pm.

Traveling in Holiday Style

And the best way to travel in holiday style? The dazzling ‘L’ train. The unique, difficult-to-miss and hard-to-catch train is a tradition during the winter months in the city. With the original holiday train hitting peak popularity in past seasons, a second train has hit the tracks of Chicago: Elves’ Workshop Train. CTA is hoping to bring a little bit of holiday cheer to your daily commute and it’s difficult to not smile once these cheery caravans pull up to your stop. Another beautiful thing about the trains (besides serving up loads of holiday joy), is that they also deliver food baskets to various charitable agencies throughout the city. To learn more about this special holiday tradition or to catch Santa on the train yourself, check out the schedule here.


Feature image via Stocksy 

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