Rebecca Engel
Chicago doesn’t soften its winters and nobody there pretends otherwise. The wind comes off the lake, the shoreline freezes into slabs of grey ice, and there are stretches of January when the high never climbs out of the twenties. The city keeps running anyway, partly because it has to and partly because it’s had a hundred and fifty years of practice.
That practice is the reason to come. Hotel rates drop, the museums empty out, the theaters and music rooms hit their busiest stretch of the year, and a good number of the city’s best traditions only exist between November and February. These are twenty one things to do in Chicago this winter, and most of them are better in the cold than they’d be in July.
1. Skate The Ribbon At Maggie Daley Park
The Skating Ribbon is a quarter mile of ice that loops through Maggie Daley Park instead of sitting in a rectangle like a normal rink. It winds around rock formations and passes under a footbridge, so it feels closer to a trail than a lap.
Skating is free if you bring your own skates and rentals are cheap enough if you don’t. Weekend afternoons fill up fast, so a weekday morning is the easy win.
The view is what makes this the one to pick. You’ve got the Michigan Avenue skyline directly over your shoulder the whole way around, which no indoor rink is going to match.
2. Wander The Christkindlmarket At Daley Plaza
Christkindlmarket has run in Daley Plaza since 1996 and it’s modeled on the Christkindlesmarkt in Nuremberg. Wooden stalls, a lot of German vendors, and a great many people packed into one downtown square.
Come for the food more than the shopping. Bratwurst, potato pancakes, roasted nuts, and hot spiced wine served in a collectible boot mug with a new design every year.
Go on a weekday if your schedule allows it. Weekend evenings in December are shoulder to shoulder and the lines for food get genuinely long.
3. Walk Through ZooLights At Lincoln Park Zoo
ZooLights strings a couple of million lights through the trees and along the paths at Lincoln Park Zoo, and it runs most nights from late November into early January.
The zoo itself is one of the last free zoos in the country, though ZooLights has moved to reserved tickets on some nights, so it’s worth checking the calendar before you make the trip.
Dress for it properly. This is an outdoor walk in the dark in Chicago in December, and the hot chocolate stands along the route are there for a reason.
4. See Christmas Around The World At The Museum Of Science And Industry
The Museum of Science and Industry has been putting up Christmas Around The World since 1942, when it was a single tree honoring the Allied nations. It’s now more than fifty trees, each one decorated by a different community in the city.
The Grand Tree in the rotunda runs several stories up, and a Holidays of Light section covers the winter celebrations that aren’t Christmas.
It’s included with regular museum admission, so it stacks onto a day you were already planning to spend indoors.
5. Sled Down Cricket Hill In Lincoln Park
Chicago is famously flat, which turns the handful of real hills into a big deal the moment it snows. Cricket Hill sits in Lincoln Park near Montrose Harbor and it’s the one everybody heads for.
The run isn’t long, but it’s steep enough to be worth the walk back up and wide enough that a crowd doesn’t ruin it. Bring your own sled because nothing is rented up there.
The lake sits right behind it, so from the top you get the skyline to the south and open water to the east.
6. Eat Your Way Through Chicago Restaurant Week
Restaurant Week lands in late January and early February, which is the deadest stretch of the year for the city’s restaurants and exactly why it exists.
Hundreds of places put out fixed price menus for it, and the list runs from neighborhood spots all the way up to rooms that are near impossible to get into the rest of the year.
Book early. Reservations open weeks ahead and the best tables go within days of the list being published.
7. Celebrate Lunar New Year In Chinatown
Chicago’s Chinatown throws one of the bigger Lunar New Year parades in the country, usually on a Sunday in late January or February depending on where the date falls.
Lion dancers, floats and firecrackers work their way down Wentworth Avenue while the restaurants on either side stay packed straight through the afternoon.
Get there early if you want a table, or eat first and watch second. Trying to do both at once on parade day doesn’t really work.
8. Walk The Auto Show Floor At McCormick Place
The Chicago Auto Show takes over McCormick Place in February and it’s the largest show of its kind in North America, which is a strange title for a city this cold to hold.
There are well over a thousand vehicles spread across roughly a million square feet, and unlike a lot of auto shows you’re allowed to climb into most of them.
It’s an easy way to burn four hours indoors on exactly the weekend when the weather outside is at its worst.
9. Warm Up Inside The Garfield Park Conservatory
The Garfield Park Conservatory is two acres of plants under glass on the West Side, and in February it’s comfortably the warmest and greenest place in the city.
Jens Jensen designed it in 1908 to read as a landscape rather than a greenhouse, which is why the Fern Room looks like a prairie river scene instead of rows of pots on benches.
Admission is free, though it’s worth checking whether you need to reserve a time slot. It’s a straight run out on the Green Line, and going on a grey day is the entire point.
10. Look Up At The Tiffany Dome In The Chicago Cultural Center
The Chicago Cultural Center was the city’s first public library, and the dome in Preston Bradley Hall is the largest Tiffany dome anywhere. It runs about thirty eight feet across and holds something like thirty thousand pieces of glass.
The whole building is free and nobody stops you wandering it. There are two grand staircases in marble and mosaic before you even get up to the dome.
Free concerts and exhibitions run through the week, so it’s worth a look at the schedule before you turn up rather than after.
11. Tour The Gilded Age Rooms At The Driehaus Museum
The Driehaus Museum is a restored 1883 mansion just off Michigan Avenue, built for a banking family and later rescued by a collector who filled it with period furniture, glass and lighting.
It’s small enough to see properly in about ninety minutes, which makes it the right call on a day when another enormous museum sounds like work.
The house runs a decorated holiday season through the winter, and the stained glass and lamps hold up regardless of what time of year you go.
12. Spend A Cold Afternoon At The Museum Of Contemporary Art
The MCA sits just off Michigan Avenue behind the Water Tower, and it’s one of the largest contemporary art museums in the country while pulling a fraction of the Art Institute’s crowds.
The collection covers work made since 1945 and the exhibitions rotate hard, so it’s rarely the same museum twice in one year.
Illinois residents get in free on Tuesdays. The stairway and the window looking out toward the lake are worth a few minutes on their own.
13. See The Free Galleries At The National Museum Of Mexican Art
The National Museum of Mexican Art sits in Pilsen and holds one of the largest collections of Mexican art in the country. Admission has been free since it opened in 1987 and it’s stayed that way.
The permanent collection runs from ancient work all the way through to contemporary Chicago artists, and the Day of the Dead show each autumn is what it’s best known for.
Pilsen justifies the trip on its own. The murals along 16th Street and the bakeries on 18th make an easy afternoon wrapped around the museum.
14. Dig Into The City’s Past At The Chicago History Museum
The Chicago History Museum sits at the south end of Lincoln Park and covers the fire, the World’s Fair, the stockyards and the city’s music, which is a lot of ground for one building to hold.
The Fair section is the standout. Chicago built a temporary white city on the lakefront in 1893 and then lost nearly all of it, and this is where that story actually lands.
It’s a short walk from the zoo, so the two pair up neatly on a day you’re already that far north.
15. Settle In For A Long Lunch At The Berghoff
The Berghoff opened on Adams Street in 1898 and it still has the dark wood, the tile floor and much the same German menu it’s been putting out for over a century.
It holds Chicago liquor license number one, which it collected the day Prohibition ended after spending those years quietly selling root beer instead.
Order the sauerbraten or the schnitzel and take your time over it. It’s the kind of room that makes an hour indoors feel like a plan rather than a retreat from the weather.
16. Catch A Set At Buddy Guy’s Legends
Buddy Guy’s Legends is the best known blues room left in the city, down on Wabash in the South Loop, and it puts live music on every night of the week.
January is its biggest month by a distance. The club books a run of shows that sells out well ahead, so look at the calendar before you build the rest of the trip around it.
Get there early enough for a table and plan to eat there. The kitchen does Louisiana food and the room fills up long before the headliner goes on.
17. Hear Late Night Jazz At The Green Mill
The Green Mill has been open in Uptown since 1907 and it looks every bit of it, which is precisely the appeal. Booths, a long curved bar, and low ceilings that keep the sound in the room.
Al Capone’s outfit ran the place through Prohibition and there are tunnels underneath it. The Sunday night poetry slam started here in 1986 and invented the format that every other city copied afterward.
Music runs late and cash is easier than a card. Talking through a set is the one thing the room genuinely won’t tolerate.
18. See A Show At The Second City
The Second City opened in Old Town in 1959 and the list of people who came through it is faintly absurd. Belushi, Murray, Fey, Colbert, Poehler, and a long line behind them.
The mainstage revues change a few times a year, and there’s a free improv set after most shows if you just stay in your seat when it ends.
Weekends sell out, so book ahead. Old Town is a good neighborhood to eat in beforehand rather than after.
19. Take In The Symphony At Orchestra Hall
The Chicago Symphony plays at Orchestra Hall on Michigan Avenue, a building put up for the orchestra in 1904, and its brass section is what the ensemble is most famous for worldwide.
The season runs right through the winter, which is when the programming is heaviest and the hall is doing what it was built to do.
Cheap seats exist and they’re worth taking. The upper gallery is steep and a long way back, but the sound in that room carries perfectly well up there.
20. Watch The Blackhawks At The United Center
The United Center is out on the Near West Side and it houses both the Blackhawks and the Bulls, so there’s a game on most nights through the winter.
The Blackhawks crowd is worth seeing on its own terms. The anthem gets cheered straight through at full volume rather than listened to politely, and it’s been that way since 1985.
Tickets are far easier to come by than a Cubs game in July, and the entire evening happens indoors.
21. Slurp A Hot Bowl Of Pho On Argyle Street
Argyle Street in Uptown is the city’s Vietnamese stretch, a few blocks of restaurants, bakeries and grocers gathered around the Red Line stop.
A bowl of pho on a February afternoon is one of the better things this city does, and most of the places along here are cheap and stay open late.
The train stop has a pagoda style roof, the only one on the whole L, put there to mark the neighborhood. It’s a useful landmark when everything else is under snow.
A Few More Things To Do In Chicago In The Cold
The McCormick Tribune Ice Rink in Millennium Park is the other place downtown to skate, sitting right beside the Bean, and it’s free if you’ve brought your own skates. It’s smaller and busier than the ribbon, but nothing beats it for location.
The Lincoln Park Conservatory is the smaller, closer cousin of Garfield Park. Four glass houses, free to walk through, and about twenty minutes well spent if you’re already up at the zoo.
Navy Pier runs Winter WonderFest indoors through the season, which is pointed squarely at families and does the job on a day when nobody wants to be outside at all.
And when the lake properly freezes, the shore along North Avenue and Montrose stacks up into ice shelves that look nothing like the beach does in July. Stay off them. They’re unstable, they sit over open water, and people go through every winter.
Final Thoughts
Chicago in winter asks something of you that the summer version doesn’t. You have to dress for it properly, and you have to accept that on some days the wind is simply going to win.
What you get back is a city running at full speed with a fraction of the visitors. The best things to do in Chicago in winter are mostly indoors and mostly cheap, and the traditions that carry December and January don’t exist at any other time of year.
Pick two or three of the big outdoor ones, build the rest of the days around the museums and the music rooms, and leave yourself room to duck inside when you need to. That’s how the people who live there get through it.
