When we picture a day out in Chicago, we’re probably imagining laying out in the sun on Montrose Beach, or taking in a concert in Millennium Park, or perhaps walking the Lakefront trail. But just as New York is famously the City That Never Sleeps, Chicago may just as well be the city that never hibernates. Just because the temperature drops, doesn’t mean there is any shortage of things to do during the winter, so if you, your family, or a loved one are itching for a reason to get out of the house, there is more to do in Chicago in the winter than you might expect.

Dress for Winter in Chicago

First things first, let’s talk about how to get ready for the cold. With average temperatures just barely cracking 30 degrees, Chicago winters can be unforgiving to the unprepared. If you’re looking to tackle the Windy City in the winter months, it starts with your outfit. The best thing to remember is to dress in layers. Depending on how long you’ll be out in the elements, the most versatile approach is a layer to insulate topped with a heavier coat, ideally something water-resistant. Remember; you won’t stay warm if you don’t stay dry. Don’t forget to accessorize with a proper pair of boots, gloves or mittens, and a nice hat. Naturally, if it’s too warm you can always lose a layer if need be. It’s better to find out you’re a little too toasty than to realize you’ve under dressed. 

So now that we’re dressed and ready for adventure, what can we do in Chicago in the winter?

Things To Do In Chicago During the Winter

Get Outside!

Visit Chicago’s Major Attractions — They’re Open in Spite of the Cold

The most important thing to remember is that with a few exceptions, most of Chicago’s major attractions are still open in spite of the cold, but often with modified hours and schedules. Unless you’re planning for a weekend on the beach, you shouldn’t find yourself too limited by a Chicago winter. First-time visitors may be surprised to see how active Chicagoans are even in the dead of winter. It can’t be overstated how important it is to get outside and soak up some sunshine, especially with the limited amount of daylight we may see over the winter. 

Photo by Sawyer Bengtson on Unsplash

Don’t Miss Out on Sledding

First and most importantly, what kind of Midwestern winter would it be without sledding? For a city and region as flat as it is, there are few people raised in Chicago that don’t have fond memories of weekends and evenings spent rocketing down a hill on a plastic saucer. If a fresh coat of snow has recently fallen, bring your sled to Cricket Hill in Lincoln Park (with parking located just off west Montrose Ave), where views of the skyline and the lake can make even a grey winter day the start of a lifelong memory.

Winter Stroll Through Lincoln Park or the Lakefront Trail

If the conditions aren’t quite right to go sledding, instead consider a walk through Lincoln Park or the Lakefront Trail. Often cold winter days have great visibility and little cloud cover, making for wonderful panoramas of Chicago’s famous skyline. We recommend a long but rewarding stroll from Lincoln Park south towards Navy Pier, stopping near Oak Street Beach for photos of the John Hancock Building. If you’ve still go the energy, continue south to the Museum Campus or even further to Promontory Point; both of which boast excellent views from some of Chicago’s favorite lakefront parks.

Photo by Jonathan J. Castellon on Unsplash

Live Theatre

Chicago’s theatrical tradition can be traced back at least as far as 1834, just one year after the incorporation of the city itself! While Chicago’s theatre scene may always work in the shadow cast by the giants in New York City, Chicago theatre is lively, vibrant, and ingrained with the same blue collar work ethic that inspired Carl Sandburg to dub it the “City of the Big Shoulders.” This is why there are as many as two hundred active theatre companies here at any given time, and winter is the heart of their season.

If you want to take the family to see some of Chicago’s biggest plays and musicals, the Loop is home to some of the city’s largest productions and touring companies. The James M. Nederlander Theatre (24 W Randolph), the Cadillac Palace Theatre (151 W Randolph), and Chicago Shakespeare (800 E Grand) feature some of Chicago’s biggest shows, often before they make it to NYC!

For a mix of familiar favorites, revivals, and new emerging works, Chicago’s regional theatres such as Steppenwolf (1650 N Halsted), Goodman (170 N Dearborn), and Lookingglass Theatre Company (821 N Michigan Ave) offer top-notch productions. If you would like to try something a little more informal, take in some improv or stand-up comedy from one of SNL’s most fertile grounds for recruiting future cast members, The Second City (1616 N Wells St).

Photo by Neal Kharawala on Unsplash

Shopping

Now that the holiday rush is over and crowds have largely left, it may be the perfect time to take a stroll on the Magnificent Mile; Michigan Avenue. Located in the heart of Chicago, the Mag Mile is known for being the epicenter of high-end retail in Chicago and this may be the perfect time of year to do some window shopping. Stretching from the Chicago River on the south, all the way up to Oak Street on the north, there are over 400 stores and over 200 restaurants, so no matter if you want an intimate boutique experience or would prefer to see the flagship retail locations of some of your favorite brands, there is something for everyone. For a little historical flair while you walk, start your trip at the corner of the Michigan and Wacker at the site of the original Fort Dearborn and work your way up north to the original Water Tower, a surviving remnant of the Great Chicago Fire of 1871.

Go on a Walking Tour of Chicago

During the winter, there’s no shortage of options for taking a guided walking tour of Chicago. Now that there is a chill in the air and more than likely some snow on the ground, the ever-popular architecture cruises and city bike tours may not be everyone’s cup of tea. However, a guided walking tour with Bobby’s Bike Hike is a great way to experience the city while staying comfortably warm.

The Chicago Favorites Food and Walking Tour features classic, soul-warming Chicago foods like deep dish pizza, fully-loaded Chicago style hot dogs, Italian beef, and more, all while learning the stories you might not know about some of the city’s best-known landmarks. For those over 21; ask about the VIP upgrade, which features a sampling of local beers to really round out the local flavors we are known for. The tour runs in any weather, so dress accordingly and show up with an appetite!

  • Active Chicago Food Tours

    Chicago Favorites Walking & Food Tour

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    11:30am Daily, 5:30pm Fri-Sat

    HIGHLIGHTS: Chicago Food Staples, Deep-Dish Pizza, Chicago-Style Hot Dog, Italian Beef Sandwich, Millennium Park, The Loop, Chicago Riverwalk

    Lou Malnati’s Pizzeria – Wrigley Building
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    AGE
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    LENGTH
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    11:30am Daily, 5:30pm Fri-Sat
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    11:30am Daily, 5:30pm Fri-Sat
    DURATION
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    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $69.99 $65.99
    Youth (Ages 4-11) $59.99 $55.99
    Infants (Ages 0-3) when sharing w/ adult $10.99 $9.99
    VIP Craft Beer Tasting Upgrade $19.99
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    Highlights
    Chicago Loop
    Chicago Style Deep Dish Pizza
    Millennium Park
    Chicago Theater
    Italian Beef Sandwich
    Riverwalk
    Chicago-style Hot Dog
    State Street
    Michigan Avenue
    Dessert
    VIP Craft Beer Package upgrade
    PRICE
    Discount Online Rates at $69.99
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  • Chinatown Food & Culture Walking Tour

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    4pm Friday - Sunday

    HIGHLIGHTS: Cantonese Dim Sum, Portuguese-Chinese Bakery Treats, Xi'an Cuisine, Sichuan Dry Chili Chicken, Yummy Noodles

    Phoenix Restaurant – Chinatown
    Kids under 12
    Kids under 4
    Students / Seniors 65+
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    Private Group Request
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    Adult
    $69.99
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    AGE
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    SCHEDULE
    4pm Fri - Sun
    Custom Line
    4pm Friday - Sunday
    Reserve Now
    PRICE

    (Discount Online Rate includes Food Samples.)

    Price: Fri-Sun Mon-Thurs
    Adults $69.99 $65.99
    Youth (Ages 4-11) $59.99 $55.99
    Infants (Ages 0-3) when sharing w/ Adult $10.99 $9.99
    VIP bubbly tea, Beer/Wine Tasting Upgrade $19.99
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    Highlights
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    Dim Sum Treats
    Egg Tarts
    Lamb & Cumin Sandwich
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    VIP Upgrade for beer, wine and bubbly tea
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Lincoln Park Zoo

Lincoln Park has been one of Chicago’s most prominent green spaces since the mid-19th century, and while some seasons are less green than others, Lincoln Park zoo remains open year-round. As one of the oldest zoos in America, generations of visitors have marveled at the thousands of animals on display, including big cats, bears, great apes, and its instantly recognizable flamingos, all of which can be seen year-round. Lincoln Park zoo also features a children’s zoo, which helps promote their message of education and conservation, encouraging kids to think about the species they may see in their own backyards. Admission is free, so take the family out to one of the several on-site restaurants and make a donation to help support the Lincoln Park zoo.

Photo by Marisa Barrett on Unsplash

Garfield Park Conservatory

Located a few miles west of the city, the Garfield Park Conservatory (300 N Central Park Ave) is a hidden gem for family activities. With a full two acres of public greenhouse space grouped by habitat and climate, families can escape the elements and tour the conservatory together, letting their imaginations transport them from cold and blustery Chicago to the deserts of the American Southwest or even the balmy tropics. The family will love taking a day away from the freezing cold to see this explosion of green, itself located conveniently just steps away from the Green Line. While this attraction is free, make sure to reserve tickets online ahead of time.

Photo by J. Brouwer on Unsplash

Shedd Aquarium

Located in Chicago’s Museum Campus, The Shedd Aquarium is home to more than 1,500 species of aquatic life, including thousands of saltwater and freshwater fish, turtles, otters, alligators, and much more. There is something endlessly fascinating and other-worldly about seeing all these creatures close-up and adults and children alike are guaranteed to be awestruck at the experience. First-time visitors absolutely must watch a dolphin show in the Shedd’s Oceanarium, the largest indoor marine mammal facility in the world. For those that think they’ve already seen it all, be sure to look into the Shedd’s animal experiences. These experiences include the chance to feed a shark, meet a beluga whale, or even pet a penguin! 

Photo by Lance Anderson on Unsplash

Winter Date Ideas in Chicago:

Whether you’re planning a first date or are simply enjoying a night out with a loved one, Chicago has no shortage of options for an unforgettable date. Sure, the tried-and-true dinner and a movie date still works, but with so many amazing things to see and do in the city, there’s no reason not to go on an adventure for two.

Ice Skating Dates During Winter in Chicago

Just because it’s cold outside doesn’t mean there isn’t fun to be had outdoors. Usually as early as November every year, Chicago transforms several outdoor spaces into ice skating rinks, including locations on Michigan Avenue, Hyde Park, and Millennium Park among others. The skating ribbon in Maggie Daley park is one of the city’s favorites, so be sure to reserve your spot online before you go. Most skating rinks will offer skate rentals, so all you need is a warm coat and a partner to enjoy the experience with. The best part about skating is that it’s still great fun even when you’re bad at it, so plan your date around having a good laugh at your own expense, and when you’re all done be sure to wrap up the experience with a rich hot chocolate from a nearby cafe.

Photo courtesy Bobby’s Bike Hike

Museums Dates in Chicago

Chicago is home to multiple world-class museums, meaning there is truly something for everyone, and with an average ticket price from about $25 (or even free!) there are options for everyone’s budget. Among these are perennial favorites like the Art Institute of Chicago, the Museum of Science and Industry, and the Adler Planetarium.

However, if you and your date want to stray from the beaten path, you would be smart to check out some eclectic options like the International Museum of Surgical Science, the American Toby Jug Museum, or the decidedly more macabre Medieval Torture Museum. No matter what you choose, any of these exhibits will certainly spark your imaginations and conversations.

Photo by Chris Nguyen on Unsplash

Barcade Dates During Chicago’s Winter

For a more energetic spin on a winter date at your local watering hole, one of Chicago’s many barcades just might fit the bill. Billiards and darts are still a mainstay of just about every corner bar, but for some variety including pinball machines, classic arcade cabinets, and air hockey you have to check out one of Chicago’s several adult-oriented arcades. With a recent boom in these hybrid bars, you can expect to see several choices across the city, from the Headquarters Beercade near downtown or Emporium in both Logan Square and Wicker Park, you’ll find no lack of options. One highlight to check out if you find yourself on the north side is Replay. With locations in Lakeview and Lincoln Park, Replay is known for their immersive themed pop-up experiences, with previous exhibits such as The Office, Harry Potter, and Nickelodeon-styled events. So grab a drink and your favorite Player 2, because Chicago’s barcades are a great pick for an energetic date night.

Photo by Kyle Nieber on Unsplash

If you’re visiting Chicago for the first time this winter or if you’re a local just looking for an excuse to have some fun while braving the cold, there is no shortage of things to do this winter; all you need is a sturdy coat and a sense of adventure.