Best Chicago Winter Activities: Beyond Ice Skating

Brisk city sidewalks, the glow of holiday lights, cozy spots for hot chocolate, and the stunning skyline sparkling against the winter sky—welcome to Chicago in winter!

Get ready for the ultimate city-winter experience. I know—this has been said before, but it’s true! Chicago in winter is like walking into a scene from a classic holiday movie. Not the ones where Uncle Bob is falling asleep in the corner after too much turkey, but the ones where the main street is all lit up, couples are skating hand-in-hand, the air is filled with the smell of roasted nuts, and you can’t help but be swept up in the holiday magic.

It’s a season of lights, laughter, and yes—a bit of chill, but with layers and a sense of adventure, you’re all set for an unforgettable winter in Chicago!

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• 15-page Chicago Travel Guide 

If you’re planning to visit Chicago in winter, you’re in for a truly magical experience! While the city can get incredibly cold, there’s something special about cozying up with a warm drink, taking in the holiday lights, and exploring the snow-covered streets. Here’s everything you need to know to make the most of your Chicago winter adventure.

How Cold Does It Get in Chicago This Time?

Let’s start with the reality check: Chicago winters are no joke! Temperatures can dip below freezing, with January often being the coldest month, averaging between 18°F (-8°C) and 32°F (0°C). Wind chill can make it feel even colder, so be ready for some intense blasts of “Chicago chill.” But don’t let that scare you off—seeing the city covered in snow has its own charm, and with the right layers, you’ll be just fine.

How Do I Get Around Chicago in Winter?

Navigating the city in winter isn’t as tough as it sounds. Here are some of the best options:

1. Public Transit (CTA): The “L” trains and buses are great for getting around and avoiding icy sidewalks. The city keeps public transit running smoothly even in the snow, and it’s a warm, cozy way to explore.
2. Rideshares and Taxis: Sometimes, taking a quick Uber or Lyft is worth it to avoid walking in the cold. Taxis are also readily available, especially in busy areas and downtown.
3. Walking: Many of Chicago’s must-see sights are close together, so if you’re dressed warmly, walking can be enjoyable. Just make sure to bundle up, wear insulated boots, and keep an eye out for icy patches!
4. Your private car: Once you’re in the city, finding parking can be tricky, especially in busy winter months, but SpotHero makes it easy! Don’t forget to use my exclusive link SpotHero to save 15% off on your parking.

What Apps Should I Download for Chicago?

Here are a few helpful apps I found invaluable:

• Transit App: This app will give you real-time updates on buses and trains, so you’re not left out in the cold waiting for public transit.
• SpotHero: (Enjoy 15% OFF HERE) If you’re driving, SpotHero helps you find and reserve parking in advance—a lifesaver in busy areas!
• Ventra: This app is essential if you plan to use the CTA often. You can purchase and manage your transit cards, making it super convenient to hop on buses and trains.
• Chicago Travel Guide: This app is a comprehensive mobile app that provides essential information and recommendations for your trip to Chicago

1. Ice Skating at Millennium Park: The iconic rink near “The Bean” is a must. There’s also Maggie Daley Park nearby, where you can skate along a ribbon-like path.
2. Shoreline Boat Cruise: Some companies offer winter cruises with heated cabins. Seeing the city’s architecture covered in snow is a unique experience.
3. Drunk Shakespeare Chicago: Watch Shakespeare like never before at Drunk Shakespeare, where one cast member performs tipsy while delivering classic lines. It’s a hilarious and one-of-a-kind show—get your tickets here.
4. Chicago Bulls or Blackhawks Game: Nothing says Chicago like cheering on a home team during winter.
5. Chicago Christkindlmarket: If you’re visiting in November or December, this German-style Christmas market is full of cozy holiday vibes.
6. Lincoln Park Zoo Night Out: Enjoy a festive evening of holiday lights, music, and drinks at Lincoln Park Zoo’s Adults Holidaze Night Out. Don’t forget to use code TWTR for special savings on your tickets!
7. Comedy Show: Laugh your way through a cold evening at one of Chicago’s top comedy clubs. From improv to stand-up, there’s no shortage of talent. Grab your Comedy Show Tickets for a night of guaranteed giggles
8. Hip Hop Nutcracker: Experience a modern twist on a classic with the Hip Hop Nutcracker. This electrifying performance combines Tchaikovsky’s score with hip-hop choreography for a show you won’t forget. Book your tickets now!
9. Neon Brush Kids Chicago: Unleash your creativity with your little ones at Neon Brush Kids, a family painting experience perfect for all ages. Grab your tickets for a colorful and fun-filled day.
10. Explore Navy Pier: Though some of the outdoor rides may be closed, there’s plenty to do indoors, like visiting Offshore Rooftop, Winterland, FlyOver and Light Up The Lake.
11. Ferris Bueller Movie Tour: Relive iconic moments from Ferris Bueller’s Day Off with a guided movie tour through the Art Institute of Chicago. Snag your tickets and step into cinematic history.
12. The Escape Game Chicago: Challenge your mind and teamwork skills at The Escape Game Chicago. These epic 60-minute adventures are thrilling and fun for all ages. Book your spot here and see if you can solve the puzzles in time!
13. Spray Paint ‘n’ Sip Urban Art Workshop: Channel your inner artist at the Spray Paint ‘n’ Sip Urban Art Workshop. Learn graffiti-style techniques while enjoying a relaxed, creative vibe. Tickets are available here.

Packing right can make all the difference! Here’s what I’d recommend:

• Warm, Insulated Coat: A long, down-filled coat with a hood is ideal for staying warm and keeping the wind at bay. See this option here: https://amzn.to/41uJxdv
• Layered Clothing: Start with a thermal base layer, add a sweater, and then finish with your coat. Layering helps you stay warm and lets you adjust if you’re indoors. See my favorite thermals here: https://amzn.to/3ZYWtaF
• Waterproof Boots: Insulated, waterproof boots are a lifesaver for trudging through snow and slush. Look for good grip to avoid slipping on icy sidewalks. See my favorite winter boots for Chicago here: https://amzn.to/4itcBZ5
• Accessories: Don’t forget a hat, scarf, and touchscreen gloves. You’ll want every bit of skin covered on those extra-cold days! See my favorite set here: https://amzn.to/3VCbY5t
• Hand Warmers: These are amazing for staying cozy during outdoor activities or long walks. The best hot hands hand warmers here: https://amzn.to/41u4HID
• Moisturizer and Lip Balm: The winter air can be really drying, so pack a good moisturizer and lip balm. My favorite chapstick for the winter, here: https://amzn.to/3D9hbvv

Chicago in winter is an experience that’s truly one of a kind. Sure, it’s chilly, but with these tips, you’ll be ready to embrace everything the city has to offer. So layer up, grab some hot chocolate, and get ready to see the Windy City in all its winter glory!

If you need detailed planning for your trip to Chicago without thinking too much, grab this to travel as a local!

Remember to tag @travelwiththerussells on social media to share your adventures and connect with other travelers.

Enjoy your trip to Chicago and I’m waiting for you to tag me to share your experience!