Chicago transforms into a winter wonderland when temperatures drop, and while the cold might tempt you to hibernate, there's too much happening to stay inside. From ice skating under twinkling lights to cozy museum afternoons, the city comes alive with seasonal magic.
We’re here to make this winter your best one yet. Whether you're planning a day trip with friends or organizing group outings, Chicago Motor Coach makes winter adventures easier — we'll handle the driving while you soak up everything the season offers.
1. Ice Skating at Millennium Park
Nothing says Chicago winter quite like gliding across the ice at the McCormick Tribune Ice Rink. Nestled right next to Cloud Gate (or as locals call it, the Bean), this free outdoor rink offers one of the most iconic skating experiences in the country. The skyline towers above you, the holiday lights create a magical glow, and there's something about skating in the shadow of downtown that just feels quintessentially Chicago. Make sure to get there early on weekends — this spot gets packed, and for good reason.
2. Explore the Christkindlmarket
Daley Plaza transforms into a little slice of Germany every winter, and the Christkindlmarket is where you'll find handcrafted ornaments, authentic bratwurst, and steaming mugs of glühwein. It's more than just a market — it's an experience. Wander through rows of wooden huts, pick up unique gifts you won't find anywhere else, and embrace the festive chaos. The smells alone are worth the trip: inhale the scents of roasted nuts, grilled sausages, and cinnamon everything. Bundle up and bring cash for the smaller vendors.
3. Visit the Lincoln Park Zoo's ZooLights
Free admission, millions of lights, and adorable animals — what's not to love? ZooLights turns Lincoln Park Zoo into an illuminated spectacle with light displays draped over trees, pathways, and even some animal habitats. Grab hot chocolate from one of the vendors and watch ice carvers create masterpieces. It's one of those Chicago traditions that never gets old, no matter how many times you go.
4. Catch a Show at the Chicago Theatre
When it's too cold to be outside, Chicago's theater scene heats up. The Chicago Theatre, with its iconic marquee, hosts everything from comedy shows to concerts and classic films. There's something special about settling into a plush seat in a historic venue while the wind howls outside. The architecture alone is worth seeing — those gilded interiors and grand staircases transport you back to the 1920s. Check their winter lineup and plan a fancy, memorable night out.
5. Warm Up at the Art Institute of Chicago
The Art Institute becomes an even better destination when the weather turns brutal. Spend a few hours wandering through world-class collections — from Monet's haystacks to Grant Wood's "American Gothic". The Modern Wing offers stunning views of Millennium Park, and the Impressionist galleries feel like stepping into another world. Pro tip: hit the museum café for lunch with a view. It's the perfect way to spend a frigid afternoon without sacrificing culture.
6. Go Sledding at Cricket Hill
Cricket Hill in Montrose Beach becomes sledding central when snow blankets the city. The hill isn't huge, but it has enough slope to build up speed and enough of a crowd to make it fun. Families pack the hill on snowy weekends, and there's something contagious about the laughter echoing across the park. Bring your own sled, dress in layers, and maybe pack a thermos of hot chocolate. Just be prepared — the walk back up gets tiring after the tenth run.
7. Tour the Museum of Science and Industry
The Museum of Science and Industry is massive enough to take up an entire day, which makes it perfect for when you need to escape the cold. The U-505 submarine exhibit puts you inside an actual German U-boat, the Science Storms section lets you create mini tornadoes, and the coal mine tour takes you underground. Winter is an ideal time to visit because it's less crowded than summer, and you can take your time enjoying all the exhibits have to offer.
8. Experience the Chicago Symphony Orchestra
The Chicago Symphony Orchestra at Symphony Center delivers performances that often include holiday classics and seasonal favorites alongside their regular repertoire. Even if classical music isn't usually your thing, there's something about live orchestral music in a beautiful hall that hits different. Dress up, grab drinks at intermission, and let yourself be swept away.
9. Walk Through the Garfield Park Conservatory
When you're desperate for green and growing things, the Garfield Park Conservatory is your answer. Step inside, and suddenly you're surrounded by tropical plants, humid air, and temperatures that feel like summer. The Palm House features towering palms and exotic blooms, while the Fern Room creates a misty, otherworldly atmosphere. It's free to visit, and they often have special winter exhibitions. Don’t forget to bring your camera — the contrast between the winter world outside and the lush paradise inside is striking.
10. Browse the Randolph Street Market
The Randolph Street Market continues through the winter months, offering vintage finds, antiques, and artisan goods in an indoor setting. It's treasure hunting at its finest — you never know what you'll discover, from mid-century furniture to handmade jewelry. The indoor market means you can browse without freezing, and there are always food vendors serving up something warm. Go with time to spare; you'll want to dig through everything.
11. Attend a Chicago Blackhawks Game
Hockey season means the United Center fills with fans ready to cheer on the Blackhawks. Even if you're not a die-hard hockey fan, the atmosphere during a game is electric. The national anthem alone — sung by Jim Cornelison with the crowd roaring — is an experience. Plus, there's something perfect about watching people smash into each other on ice while you're sitting safely warm inside with a beer and a hot dog.
12. Visit the Money Museum at the Federal Reserve
Here's a free activity most Chicagoans don't even know about: the Money Museum at the Federal Reserve Bank of Chicago. You'll see millions of dollars behind glass, learn about counterfeiting, try to detect fake bills, and discover how currency works. It's surprisingly interesting, completely free, and provides about an hour of indoor entertainment. Plus, you can say you visited a federal bank — not everyone can claim that.
The Best Places to Go in Chicago for Christmas
Chicago goes all-out for Christmas, turning neighborhoods and landmarks into festive spectacles worth bundling up for.
The Magnificent Mile Lights Festival kicks off the season with a parade, fireworks, and a spectacular tree lighting. Michigan Avenue becomes a river of lights, stretching from the Chicago River to Oak Street.
Navy Pier's Winter WonderFest transforms the pier into an indoor holiday playground with rides, entertainment, and enough decorations to satisfy any Christmas enthusiast. The Ferris wheel looks magical against winter skies.
The Chicago Botanic Garden's Wonderland Express features model trains winding through miniature Chicago landmarks made entirely of natural materials. It's surprisingly enchanting, even for adults.
State Street's Holiday Windows showcase elaborate displays that department stores spend months perfecting. Walking the strip to see each window's theme is a Chicago Christmas tradition.
Getting Around Chicago in the Winter with Chicago Motor Coach
Winter weather makes group transportation trickier — icy roads, limited parking, and freezing walks from distant parking spots can derail even the best-planned outings. That's where having reliable transportation changes everything.
Our fleet at Chicago Motor Coach handles Chicago winters like pros, getting your group where you need to go safely and comfortably:
56-Passenger Motor Coach Buses are perfect for large groups heading to holiday events, school field trips to museums, or corporate outings exploring the city's winter attractions.
50-Passenger Coach Buses offer similar amenities in a slightly smaller package, ideal for church groups touring Christmas lights or company teams attending downtown events.
40-Passenger Mini Buses strike the balance between capacity and maneuverability, making them great for sports teams heading to games or neighborhood holiday tours around the city.
28-Passenger Mini Buses are perfect for intimate group outings — think family reunions, exploring Christmas markets, or small tour groups hitting multiple winter attractions in one day.
14-Passenger Mercedes Sprinter Vans provide luxury transportation for executive outings, small wedding parties, or VIP groups.
No matter the vehicle you choose, you'll have a professional driver who knows Chicago's winter streets, climate controls to keep everyone comfortable, and the peace of mind that comes from not navigating icy roads yourself.
Ready to Plan Your Chicago Winter Adventure?
With our Chicago charter bus rental services, you can count on safe, reliable, and comfortable transportation for any group size. Our modern fleet, professional drivers, and flexible schedules make it easy to enjoy Chicago’s biggest holiday celebration without the hassle of traffic or parking. Get your quote now, and we’re excited to have you on board soon!
Experience Chicago's best winter activities from ice skating at Millennium Park to ZooLights. Let Chicago Motor Coach handle group transportation this season.
