It’s no secret that Chicago can get brisk in the winter. The Windy City is right on Lake Michigan, creating a lake effect that chills visitors from November till March. However, don’t let that scare you away from the city, as there is so much to do in these months that will create lasting memories. With our tips, you’ll be prepped to face the weather like a local and enjoy your winter vacation in the most iconic city in the Midwest.

What to Pack

Chicagoans know that layers are the secret weapon for surviving the city’s frosty months. The trick is to start with a thermal base layer, add a cozy sweater, and top it all off with a sturdy, insulated coat to block that famous lakefront wind that seems to cut right through you. Accessories aren’t just for style, they’re your best defense. A warm hat, soft scarf, and lined gloves will help keep the chill at bay while still looking effortlessly chic in your winter photos. Don’t underestimate the power of a good pair of boots or a pocketful of hand warmers either; they can make the difference between shivering and strolling comfortably down Michigan Avenue. With the right wardrobe, you’ll be ready to explore the Windy City in comfort and confidence.

Getting Around

With winter comes a dusting of snow that transforms Chicago into a glittering wonderland, but locals know that getting around takes a bit of strategy. Instead of trudging through icy sidewalks and snowdrifts, Chicagoans have mastered the art of staying warm on the go. The city’s public transportation system is one of the best in the country, with CTA trains and buses connecting nearly every corner of downtown and beyond. Hopping on a train instead of walking several blocks in the wind can save you from frozen fingers and rosy cheeks. 

Another hidden gem is the Chicago Pedway, an underground network of tunnels linking dozens of buildings, hotels, and train stations. It’s the perfect escape from the elements and a fun way to explore the city from a new perspective. Of course, rideshares like Uber and Lyft are always within reach if you prefer door-to-door comfort. And for those who want to take in the snowy cityscape firsthand, a leisurely stroll can still be magical, just make sure to pop into one of the city’s countless cozy cafés for a steaming cup of coffee, seasonal cocktails, or rich hot chocolate to thaw out before your next stop.

Focus on indoor attractions

Chicago isn’t short on attractions that let you escape the chill, and winter is one of the best times to experience them without the summer crowds. On Museum Campus alone, you can spend entire days exploring world-class institutions like the Shedd Aquarium, The Field Museum, and the Adler Planetarium, all connected by stunning views of the iconic skyline and Lake Michigan. For those with an eye for design, the city’s legendary architecture shines just as brightly in winter. Join a guided architecture tour or simply wander downtown to admire the intricate details and historic charm of Chicago’s most recognizable buildings amid the snow. 

If live entertainment is more your style, the theatre scene is in full swing this time of year, with Broadway shows and local productions bringing the streets to life with music and storytelling. And for an evening of elegance, the Chicago Symphony Orchestra offers performances that fill the air with warmth and wonder, creating the perfect backdrop for your winter getaway.

‍Enjoy the seasonal events

Winter is often called a wonderland for a reason, and Chicago brings that magic to life in every corner of the city. As the air turns crisp, storefronts transform with festive window displays, bows and garlands drape the streetlights, and horse-drawn carriages make their way down Michigan Avenue, bringing with them a timeless holiday charm. The beloved Christkindlmarket is a highlight of the season, drawing locals and visitors alike to sip hot mulled wine, browse handcrafted ornaments, and shop from artisans selling unique, giftable treasures. Outdoor ice skating is another essential Chicago winter pastime, whether you’re gliding beneath the shimmering reflection of “The Bean” at Millennium Park or circling the scenic Maggie Daley Park ribbon, you’ll find yourself immersed in Instagram-worthy moments. 

Evenings come alive with the glow of Lincoln Park ZooLights, a family favorite that captures the spirit of the season year after year. As the holidays fade and we step into the new year, Chicago Restaurant Week offers the perfect reason to warm up indoors, savoring creative seasonal dishes from some of the city’s most celebrated chefs. From twinkling lights to culinary delights, Chicago’s winter is a celebration of comfort, creativity, and pure joy.

Warm up after a day of adventure

No matter how chilly the Windy City gets, Chicago in winter is full of magic waiting to be explored. With the right preparation of cozy layers, clever navigation, and a mix of indoor and seasonal activities, you can experience the city like a local while creating memories that last a lifetime. When it’s time to rest and recharge, Hotel EMC2 offers a warm welcome in a central location, putting you just steps away from the city’s top attractions and seasonal highlights. From there, it’s easy to step back out and continue discovering the charm, culture, and winter wonder of Chicago. We can’t wait to see you this winter!