Oh, the weather outside isn’t so frightful! Inside your Chicago Stay Alfred is certainly delightful, but when these fun cold-weather activities are on, you’ll want to get out and explore the Windy City’s winter wonderland. The crisp lake air might chill your cheeks and Jack Frost might nip at your toes, but when the temperature drops, Chicago’s holiday spirit reaches a peak. Chi-Town pulls out all the stops during the winter season, with twinkling lights and over-the-top window displays that rival those of the Big Apple. Add a little extra sparkle to your winter getaway and check out our top 7 things to do in Chicago during winter – and don’t forget to pack some wool socks!
Celebrate the season at Chicago’s Christkindlmarket
Inspired by Germany’s legendary Christmas markets that date back to the 1500s, the Christkindlmarket in Chicago brings old world charm and mouthwatering mulled wine to the Midwest. The market opens in mid-November and runs through Christmas Eve, so you’ll have nearly six weeks to get your fill of German beer, schnitzel, and soft pretzels.
The market sets up shop on Daley Plaza in the heart of Downtown Chicago, just a couple blocks from the Cloud Gate sculpture, and shopping is certainly one of the market’s highlights. A slew of vendors sell unique and seasonal wares including nutcrackers, beer steins, jewelry, clothes, décor, and wooden handicrafts as far as the eye can see. It’s the perfect place to find holiday gifts for those on your “nice” list!
Even if you’re not in a shopping mood, the market is worth a visit for some hearty German-inspired eats and festive entertainment. Swing by one of the many food or drink stands to find sausages, potato pancakes, roasted nuts, German chocolates, and apple strudel. For the full Christkindl experience, sing along, dance, or just tap your toes the sounds of live music. Of course, it all pairs beautifully with a pint of beer or a steaming, boot-shaped glass of Gluhwein, the traditional warm wine infused with herbs and spices.
Ooh and aah at the Magnificent Mile Lights Festival
For many Chicagoans, the Magnificent Mile Lights Festival is the event that really kicks off the holiday season. And it truly is a signature Chicago experience; besides the mind-boggling amount of bright and shiny lights up and down the street, it’s a fabulous way to experience the more than 50 landmarks and attractions found on the Magnificent Mile. The festival has something for everyone, from family-friendly fun to shopping, a parade, and a jaw-dropping grand finale of fireworks over the Chicago River.
Grand marshals Mickey Mouse and Minnie Mouse bring their “Happiest Place on Earth” ethos and will be making seasons bright by illuminating more than 1 million lights on 250 trees along the route. Make sure your phone is charged – this event is definitely photo-worthy.
Our local experts report that for the most amazing aerial views of the Magnificent Mile, a visit to 360 CHICAGO’s 94th-floor observatory is in order. During the spectacular fireworks show over the Chicago River at the DuSable Bridge, standing along Wacker Drive or in Pioneer Court are the prime viewing spots. The DuSable Bridge (formerly known as the Michigan Avenue Bridge) closes as early as 3:30pm each year, so if you want to get to your favorite spot for the lighting procession, be sure to make your way across the bridge before then.
Stretch your legs at the Turkey Trot
Before you gather around the table on Thanksgiving and go for seconds (and thirds – hey, no judgement here) of those yummy mashed potatoes, you can embrace a more balanced day with a little outdoor exercise along the shores of Lake Michigan at Chicago’s annual Turkey Trot. This “fun run” includes a 5K, an 8K, and a special Plymouth Rock Ramble race just for the young turkey trotters.
Make sure to meet up with your flock of Turkey Day runners at the Turkey Day Tailgate for pre- and post-race activities like corn hole, football toss, turkey bowling and more. Prizes will be awarded to the best dressed Thanksgiving-inspired group. When else do you get to strut around the city dressed like a turkey?
But this run isn’t just fun, it also supports a good cause. You’ll be giving back to the community by supporting the Greater Chicago Food Depository and helping to ensure no Chicagoan goes hungry this holiday season.
Snap some wintry shots at ZooLights & BrewLights at Lincoln Park Zoo
It’s not only nocturnal animals that bring the zoo to life at night! During ZooLights, the Lincoln Park Zoo transforms into a winter wonderland, with multi-colored, glowing light arrangements and unique 3D displays. During this holiday celebration, you can experience musical light shows, watch live ice sculpture carving, and ride a carousel, train, or ferris wheel. Snack on winter-themed goodies or warm up with a cup of spiced wine. Or, challenge yourself and see if you can find your way out of the Light Maze!
On most nights, ZooLights is 100% kid-friendly, but a few nights each year are reserved for grown-ups. Check the calendar to see which evenings host BrewLights, the adults-only version of holiday fun at the zoo. These events present an opportunity to expand your beer horizons and taste local and seasonal brews from notable breweries like Begyle Brewing Company, Noon Whistle Brewing, Saugatuck Brewing Company, and many more.
Local tip: Going to be in town for Thanksgiving? Don’t miss the ZooLights Opening Night, which happens on the day after Turkey Day.
Glide across the rink at Ice Skating at Millennium Park
Don your best winter wear, stick some handwarmers in your pockets, and head over to Millennium Park to do a few laps around the McCormick Tribune Ice Rink. This is the perfect time to lace up those blades of glory and channel your inner figure skater – you will have no choice but to get in the holiday spirit and have a few laughs with friends and family.
Once you’re ready for some apres-skate, go across the street for a beer at The Gage or walk over to Miller's Pub, where a nice selection of craft brews is always on tap. Skating will surely work up an appetite, so you might want to plan ahead and book a reservation at the swanky Cherry Circle Room or tried-and-true Wildberry Pancakes & Cafe.
Sing your heart out during Caroling at Cloud Gate
Why limit your inner pop superstar to karaoke night, singing in the car, or hitting those high notes in the shower? Bundle up and head to Millennium Park to belt out holiday classics at Caroling at Cloud Gate. Part concert, part sing-along, this annual event features local choral groups who lead hundreds of revelers in song. Get into the holiday spirit and wear a Santa hat while you let the sounds of the season keep you warm. Bring the whole family along, since this is one of the best things to do in Chicago with kids. Make it a full afternoon and evening of winter activities; after all that singing you can always head over to the McCormick Tribune Ice Rink for ice skating under the stars.
Warm up in a festively fabulous Chicago vacation rental
Let’s face it, there are some times during the typical Chicago winter that you just don’t want to go outside. If you choose to stay in, cozy up in style at one of Stay Alfred’s fabulous vacation rentals in Chicago. Though you’ll have to provide your own holiday decor, every one of our travel apartments comes complete with a kitchen where you can whip up hot chocolate and Christmas cookies, a couch where you can watch Frosty the Snowman, and large windows that showcase the falling snowflakes.
We’ve also chosen ideal locations across the Windy City to ensure you never have to brave the cold for long to reach the city’s top attractions. From River North to South Loop, our neighborhood digs put the best of Chicago at your mitten-wearing fingertips.