Know Before You Go: Visiting Chicago in Winter

The third-largest city in the United States doesn’t stop moving, even in winter. Focus on winter events with a festive walking tour through the city’s holiday landmarks. And don’t shy away from using the L, the metro system—it’s quick and can shelter you from the cold. The less-than-perfect forecast also makes it ideal for enjoying indoor activities such as the Garfield Park Conservatory, which has one of the most impressive plant collections in the US.

There are plenty of shows at Improv Mecca, The Second City, all through the winter, too. Alternatively, if you want to embrace the area’s chilly charm, get outside the city to enjoy the nature of the Midwest at the Midewin National Tallgrass Prairie, about an hour away by car.

Chicago gets dressed up for the holidays. At the Chicago Botanic Garden, the annual Lightscape decks out the suburban green space in multicolored flair for after-dark strolls. The German-style Christkindlmarket downtown, meanwhile, offers Christmas classics such as mulled wine. For a memorable meal, you can also check out the Walnut Room restaurant in the Macy’s on Magnificent Mile, where the dining room is overshadowed by a monumental 45-foot (13.7-meter) tree.

And the best way to get around? The light-covered holiday trains, run by the Chicago Transit Authority each year on specific dates to spread holiday cheer and deliver meals to food-insecure Chicagoans—you may even meet Santa on board.

Even in the dead of winter, there’s plenty to do in Chicago. Start at one of the city’s world-class museums, such as the Art Institute, and see work by Vincent van Gogh and Georgia O’Keefe. Then, join locals at a classic dive bar or corner food stall to try one of the city’s iconic dishes: Maybe an Italian Beef sandwich on a Chicago food walking tour or a cold beer at Richard’s Bar in West Town? And despite the cold weather, there’s always a good reason to venture out from the Loop into one of the city’s many distinct neighborhoods—perhaps Logan Square for hip grub or the South Side for Black history.

Navy Pier is one of Chicago’s most famous attractions, and yes, it’s open in winter. While attractions and their opening hours vary on the boardwalk, the interior, with its shopping and dining in view of Lake Michigan, will be open even on snowy days. Make sure to book any boat tours in advance, such as a speedboat tour, many of which depart from the pier and operate on a more limited schedule than in summer. And, of course, don’t miss one of the city's best views from the top of the Centennial Wheel.

The name of the game in Chicago in winter is layers, layers, layers. Make sure you start with a warm base layer, perhaps wool for its wicking properties, then add several other layers you can strip off if necessary. On top, opt for a down jacket plus a windbreaker. Or, do as many Chicagoans and just wrap yourself in a huge parka.

If you arrive without the appropriate gear, especially if you plan to take an architecture cruise on the Chicago River despite the chill, you can shop for winter clothes on Magnificent Mile, the shopping street just north of the Loop.

No surprise here: You should plan on packing layers, hats, gloves, and thermal base layers. For families with small children, consider bringing a heavy-duty stroller to navigate snowy sidewalks. Those interested in local culture should also pack some courage—the best way to warm yourself up in Chicago is taking a shot of Malört, the local tipple infamous for its strong taste. If you instead want to spend more time outside, you might want to pack cross-country skis or snowshoes for snowy excursions beyond the city.

There’s no avoiding the chill in December, January, and February—the depths of winter, which also carry the possibility of snowfall and ice. However, November, March, and April are much more variable—it’s not uncommon for temperatures to dip early in November with gorgeous and comfortable autumn temperatures a few days later. The same goes for March and April—“slush season”—defined by their thawing and refreezing. If you’re traveling in these shoulder months, plan indoor backups if you’re counting on a lot of outside time, as you never know if low temperatures might ruin Plan A.

January is the coldest month in Chicago, with a daily mean of 26.2°F (−3.2°C). Though December and February are slightly warmer on average, don’t count on much time spent above freezing. Add to that the wind coming off Lake Michigan, which routinely creates wind chills of several degrees colder than the stated temperature, and you see why people bundle up for their winter trips to Chicago.

That said, if you get lucky and the temperature is higher, take advantage of it and utilize some of the city’s public outdoor spaces, such as the Lakefront Trail, which stretches 18.5 miles (29.8 kilometers).

Chicago requires property owners to remove snow from the sidewalks in front of their buildings the same day it falls to increase accessibility in winter. The city is prompt at removing snow from its own land, and it is also relatively flat, which may make transportation easier for wheelchair users.

Though there are several options for getting around, it’s worth noting that the Chicago Transit Authority has made strides in accessibility: 100 percent of the bus system and 103 of the 145 rail stations in the network are accessible. There are also audio announcement buttons at bus shelters that allow visually impaired riders to hear when their next bus will arrive.

• How should I get to Chicago? Chicago has two airports connected by public transport to the Loop. However, O’Hare—in the city’s north—has some of the US’s worst on-time arrival rates in winter. Choose Midway, on the South Side, if you have a choice.

• Are Chicago attractions open in winter? Yes, most Chicago museums and attractions have regular winter hours.

• What is parking in Chicago like in winter? Parking in Chicago can be difficult. Look for winter parking ban signage, which marks spots that are illegal to park in overnight from December 1 to April 1 each year.