The Perfect Winter Weekend in Chicago
Most people tell you to visit Chicago in summer. They’re not wrong, but they’re missing something. A winter weekend here is cheaper, quieter and honestly cozier than you’d expect, as long as you dress for it and plan your days around a few warm places to duck into.
In this guide
- First, what winter in Chicago is really like
- Friday night: the Christkindlmarket
- Saturday morning: the Bean and the skating ribbon
- Saturday afternoon: a big museum
- Saturday night: deep dish, then the blues
- Sunday morning: a free greenhouse
- Sunday afternoon: stay underground
- Where to stay
- What to pack
- A rough budget
- Common questions
Here’s how to spend two days in Chicago in winter, from Friday night to Sunday afternoon, with the stuff that’s actually better when it’s cold.
First, what winter in Chicago is really like
It’s cold. Daytime highs in January hover around freezing, and nights drop well below that. The real issue is the wind off Lake Michigan, which makes the lakefront feel far colder than the number on your phone.
The upside is real, though. Hotel rates in January and February are some of the lowest of the year, museums are calm, and restaurant tables you’d fight for in July are suddenly easy. December is busier because of the holiday markets and lights, so book that month earlier.
Friday night: the Christkindlmarket
If you’re visiting between mid-November and Christmas Eve, start at the Christkindlmarket. It’s a German-style holiday market with wooden stalls, ornaments, sausages and potato pancakes, and it’s been running in Chicago for decades.
Order a mulled wine. It comes in a collectible boot-shaped mug that changes design every year, and you can keep it. Go on a weeknight or right after it opens if you can, because Saturday evenings get packed. Outside the season, swap this for dinner in the West Loop.
Saturday morning: the Bean and the skating ribbon
Head to Millennium Park early, before the crowds. Cloud Gate, the giant mirrored sculpture everyone calls the Bean, looks great with snow around it and the skyline reflected in its curves. Ten minutes is plenty.
Then walk next door to Maggie Daley Park and its skating ribbon. Instead of skating in circles on a rink, you follow a quarter-mile path that loops through the park. Entry is free if you bring your own skates, and rentals are available. Reserve a time slot online on weekends, since sessions fill up.
Saturday afternoon: a big museum
Winter is museum season, and Chicago has some of the best in the country. Our pick for a cold afternoon is the Museum of Science and Industry in Hyde Park. It’s enormous, so you can spend hours inside without ever thinking about the weather.
From mid-November to early January it hosts Christmas Around the World, with dozens of trees decorated to represent different countries. Even without that, there’s a real German submarine, a coal mine you can ride down into, and a giant model railroad. Take the Metra Electric line from downtown to get there.
Prefer art? The Art Institute is right in the Loop and is just as easy to lose an afternoon in.
Saturday night: deep dish, then the blues
Cold weather is the perfect excuse for deep-dish pizza. It takes about 45 minutes to bake, so many places let you order while you wait for your table. Lou Malnati’s and Pequod’s are both reliable, and Pequod’s caramelized crust is worth the trip north.
After dinner, go hear the blues. Kingston Mines in Lincoln Park has two stages and music until late, and Buddy Guy’s Legends in the South Loop is a classic. Both are warm, loud and full of people, which is exactly what you want on a January night.
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Sunday morning: a free greenhouse
Here’s the best trick for a Chicago winter. The Lincoln Park Conservatory is a Victorian glasshouse full of palms, ferns and orchids, and it’s kept warm and humid all year. It’s free, and stepping inside from the snow feels like a quick trip to the tropics.
The Lincoln Park Zoo is right next door and is also free. In December it hosts ZooLights in the evenings, with the paths lit up for the holidays. If you’re there on a Sunday morning, a slow loop through both makes an easy, low-key start to the day.
Sunday afternoon: stay underground
Chicago has a secret weapon for bad weather. The Pedway is a network of tunnels and walkways under the Loop that links train stations, office buildings and stores. It’s not glamorous, and the signs can be confusing, but it’ll get you across downtown without a gust of wind.
Use it to reach Macy’s on State Street, where the Walnut Room has its giant Christmas tree in December. If the sky is clear, finish with a walk to the lakefront to see the ice piling up along the shore. It’s a strange and pretty sight, and you won’t need long.
Where to stay
Stay in the Loop or River North. You’ll be close to the L, the Pedway and most of the weekend’s plans, which matters when walking ten blocks in the wind isn’t fun. The Magnificent Mile has big hotels with good winter deals, especially after New Year’s.
What to pack
Bring a proper winter coat, a hat that covers your ears, gloves and a scarf you can pull over your face. Waterproof boots with good grip are important, because sidewalks get slushy and icy. Layers beat one giant sweater, since museums and restaurants are kept warm.
A rough budget
A winter weekend here can be surprisingly reasonable. In January and February, solid downtown hotels often drop well below their summer rates. The skating ribbon, the Bean, the conservatory, the zoo and the Pedway are all free, so your main costs are food, one museum ticket and a night of live music.
Honestly, the splurge worth making is dinner. Chicago’s restaurant scene is one of the best in the country, and winter is when you can actually get a table. Look out for Chicago Restaurant Week in late January and early February, when hundreds of places offer set menus at good prices.
Common questions
Is Chicago worth visiting in winter?
Yes, if you like cozy food, museums and lower prices. Just plan indoor backups for each day.
When is the Christkindlmarket open?
Usually from mid-November until Christmas Eve. Check the dates before you book.
How cold does it get?
January highs are often around freezing, with wind chill making it feel much colder.
Do I need a car?
No. The L, buses and the Pedway cover everything here, and parking downtown is expensive.
What’s the cheapest time to visit?
January and February, after the holidays, when hotel prices drop the most.
