Chicago in the Winter: 10 Magical Things to Do (Even If You Hate the Cold)

April 22, 2025
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And why… maybe… you should consider another city for your first trip.

I’ll be honest with you — I lived in Chicago for two years and love the city. The skyline, the lakefront, the deep-dish pizza, and that classic Midwestern spirit? Absolutely unforgettable. But if you’re visiting the U.S. for the first time in the dead of winter, and you only have time for one city, let me play devil’s advocate.

Yes, Chicago is magical in the snow. But much of what makes it truly beautiful? That’s outdoors — and in the winter, much of it hibernates. That being said, if you’re bundled up and bold, here are 10 wonderful things you can do in Chicago in the winter — plus a few honest thoughts on why you might want to save it for a summer trip instead.

❄️ 1. Skate at Millennium Park Under the Bean

There’s something magical about gliding across the McCormick Tribune Ice Rink with the Bean reflecting the city lights. It’s postcard-perfect. If you don’t skate, just grab a hot cocoa and watch — it’s still charming.

✋ But: Millennium Park is usually bustling in summer with music, picnics, and people. In winter, it’s lovely — but quieter, more introspective.

🏰 2. Walk Through the ZooLights at Lincoln Park Zoo

This free zoo transforms into a twinkling winter wonderland. It’s festive, family-friendly, and completely walkable — as long as you’re layered up.

✋ But: Wind off Lake Michigan can be brutal. If you’re not used to it, you might be over it in 30 minutes flat.

☃️ 3. Stroll Through the Snow at Maggie Daley Park

There’s a winding skating ribbon and peaceful snow-covered paths with skyline views. This is where winter in the city can feel like a snow globe.

✋ But: The full charm of Maggie Daley and nearby Grant Park is in their wide-open green spaces and outdoor art — harder to enjoy when your eyelashes are frozen.

🍕 4. Warm Up in a Cozy Pizzeria

Lou Malnati’s, Pequod’s, Giordano’s — deep-dish pizza is practically a Chicago rite of passage. Winter is actually the perfect time to indulge.

✅ Pro tip: Locals hibernate in pubs and pizzerias — it’s the coziest part of the season and a great way to meet real Chicagoans.

🏒 5. Catch a Bulls or Blackhawks Game

Winter = sports season. The United Center is buzzing with energy, and if you time your trip right, you might catch a major game without breaking the bank.

🎟️ Tickets aren’t always crazy expensive — unless it’s playoffs or a holiday.

🧊 6. Marvel at Frozen Lake Michigan

Seriously, you’ve never seen anything like the icy formations along the lakefront. It’s surreal, beautiful, and uniquely Chicago.

✋ But: It’s also very cold. You’re not walking along the riverfront or lakefront for long unless you’re determined.

🍻 7. Escape to a Dive Bar

Chicago has an excellent dive bar culture. Warm interiors, cold drinks, and friendly locals who’ll chat with you all night.

✅ Bonus: Winter means everyone’s indoors — perfect for social vibes.

🧣 8. Visit the Art Institute of Chicago

Home to American Gothic and A Sunday on La Grande Jatte, this museum is world-class and blissfully heated. You could easily spend a day here.

🎨 Perfect indoor day escape when it’s freezing outside.🧊 9. Explore the Chicago Architecture Center

Chicago’s architectural heritage is one of its strongest draws — and while the riverboat tours shut down for winter, you can still geek out indoors.

✋ But: Honestly, the real beauty is seeing it from the river. The boat tours and summer skyline views just hit differently.

❄️ 10. Take a Snowy Photo Walk

Bundle up and explore the snowy streets, vintage neighborhoods like Old Town or Wicker Park, and murals in Pilsen. The city’s character still shines.

🥶 But: You’ll probably be ducking into cafés every 20 minutes to warm up.

❓So… Should You Go to Chicago in the Winter?

If you’re already set on Chicago — go! You’ll have a memorable time. But if it’s your first U.S. trip and you’re choosing just one city, here’s the case for waiting:

Chicago is a summer city. From beach days on Lake Michigan to outdoor concerts, festivals, and rooftop bars, Chicago truly comes alive in warm weather.
Transit is not tourist-friendly. Many CTA train stations are open-air, and getting between tourist spots often requires transfers or walks.
Some experiences are shut down. No boat tours, limited activity at Navy Pier, and outdoor spaces are less lively.

🇺🇸 Better Alternatives for Winter?

🌆 New York City in December–January

Think festive lights, iconic department store windows, the New Year’s ball drop, and world-class museums. Most attractions are indoors, transit is efficient, and it’s still cold — but not Chicago cold.

🌵 Las Vegas & Arizona (in Winter)

Incredibly mild and sunny. Vegas is lively year-round, and Arizona’s desert hikes (like Sedona and the Grand Canyon) are ideal in winter. It makes more sense to see these places in January than in the scorching 110°F summer heat.