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Know Before You Go: Visiting Chicago in Winter

Cold-weather tips for the Second City.

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Hi, I'm Liam!

Liam Greenwell is a writer and teacher based in Mexico City. He is originally from Cambridge, Massachusetts. You can read more of his work at liamgreenwell.com and find him on Twitter @liam_greenwell.

Chicago’s winter is notorious, a bonding experience for newcomers and old-timers alike. In addition to the Windy City’s namesake gusts off Lake Michigan, there is enough snow, slush, and frigid temperatures to make even hardened Chicagoans second-guess their life choices.

But all is not lost. Though the weather in Chicago may be brutal, there are plenty of holiday events, winter attractions, and indoor activities to keep spirits up. Read on for Chicago winter travel tips to make an off-season excursion worthwhile.

What should I do in Chicago in winter?

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Foto: Roy Harris / Shutterstock

Museums, bars, and neighborhood-hopping.

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.

How cold does Chicago get in winter?

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Below freezing.

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 as a visitor 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).

What holiday events take place in Chicago in winter?

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Family-friendly celebrations.

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 like 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.

What should I wear in Chicago in winter?

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Bundle up.

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](https://www.viator.com/Chicago-attractions/The-Magnificent-Mile/overview/d673-a3871#overview), the shopping street just north of the Loop.

How long does winter last in Chicago?

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Three months…or is it six?

There’s no avoiding 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.

Is Chicago worth visiting in winter?

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Foto: Nagel Photography / Shutterstock

Plenty to do and see despite the weather.

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 is 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. 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.

Is Navy Pier open in the winter?

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Yes, ferris wheel included.

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.

What should I bring to Chicago in winter?

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Foto: kozer / Shutterstock

Warm clothing and a dose of flexibility.

No surprise here: visitors should plan on packing layers, hats, gloves, and thermal base layers. For families with small children, consider packing 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. Those who want to spend more time outside may want to pack cross-country skis or snowshoes for excursions outside of the city.

Is Chicago accessible for disabled travelers in winter?

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Foto: wonderlustpicstravel / Shutterstock

Snow removal and accessible transit.

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% 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.

Frequently asked questions

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Everything you need to know about visiting Chicago.

  • How should I arrive in 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 Dec. 1 to April 1 each year.

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