3 Quick Winter Getaways, And What To Wear When You Go

After a very slow start, winter has finally arrived in Chicago, officially marking the countdown to a city-wide cold-weather burnout. If you're dying to get out of Dodge, but don't want to deal with airport security, you've come to the right place. We've planned three super-easy getaways — from sleek museums to stylish ski spots — that happen to be within driving distance but will feel worlds away. And what to wear? We took care of that, too (naturally). So, grab your credit card and fill up your gas tank — we promise you can enjoy a badass break without using a single vacation day. No excuses — it's not like you have to worry about what to pack.
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Who says the Midwest is too flat for any snowy fun? Channel your inner ski bunny at this Wisconsin resort located just two hours away from the city. So what if you’ve never skied or snowboarded! It’s the perfect excuse to invest in some weather-proof threads that will make sure you look hot whether you end up holding down the slalom or getting bandaged up by ski patrol.
JBNY Glossy Down Parka, $197, available at Nordstrom. L.L.Bean Shearling 10” boot, $159, available at L.L. Bean. Topshop Hamper Check Shirt, $56, available at Topshop. Jack Spade Air Quote Mittens, $61.75, available at Jack Spade. Kate Spade Head in the Clouds Ski cap, $42, available at Kate Spade.
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While Chicago has plenty of museums, none are as architecturally stunning as the Milwaukee Art Museum. Take a short drive north to see the “Sexiest Building in the World” designed by Santiago Calatrava. Featuring an incredible exhibit on Outsider art, you’ll feel like an insider in these cosmopolitan looks fit for the gorgeous space itself.
Need Supply Co. Draped Wool Coat $68, available at Need Supply Co. Sonia by Sonia Rykiel Striped cotton-blend and silk-chiffon dress, $140, available at The Outnet. Hansel from Basel Chunky Rib Thigh Hi, $32, available at Hansel from Basel. Freebird by Steven Heathrow Boot, $328, available at Free People. Inverted Triangle Necklace, $48, available at Need Supply Co.
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Vintage hatboxes, pristine hard-shell train cases, and candy colored mid-century furniture are just a few things you’ll want to spend your rent money on in South Haven, particularly at Sweet Pickin's Antiques. Make sure you're travelling light so there's plenty of room in the car for all of your finds. Finish your trip with a drive along the lake at sunset — you can’t miss it.
A.P.C. Women's New Cure Jeans, $175, available at A.P.C.. T. Babaton Caroline Blouse $115, available at Aritzia. Burberry Brit Gabardine Parka, $795, available at Net-A-Porter. Topshop Taupe Silver Lurex Tights, $20, available at Topshop. Jeffrey Campbell Suede Zip Back Booties, $165, available at Jeffrey Campbell.
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