No, We're Not Crazy: 10 Reasons Why Chicago is Better in Winter
A Chicago winter is cold — but don’t let it keep you away (Stocksy)
As a lifelong Chicagoan, I get very defensive when people talk smack about my city, especially when winter is concerned.
Yes, it can get cold. Yes, it can snow. But if that’s all you know, then you don’t know Chicago. The city’s winter chill for too long has eclipsed the cultural treasures found even in the coldest and darkest months.
Cabo and Cancun can wait. So find your winter coat, a pair of gloves — and your sense of adventure. Here are 10 reasons to trade clichéd tropical destinations for a Chicago getaway this winter instead. And no, it’s not as crazy as it sounds.
Hotel Discounts
As the temperature drops, so do the prices at hotels across Chicago. The savings are crazy: Hotels that command $300 per night other times of year can easily fetch between $100 and $150 per night in winter. Sometimes even less. Case in point: Hilton’s Chillcation program offers rates as low as $85 a night at properties like the Palmer House Hilton, a landmark palace hotel that recently underwent a massive overhaul.
Easy Access
Flying into a Chicago winter wonderland (Getty Images)
Chicago is a major transportation hub with nearly every airline flying into one or both of its major airports, Midway and O’Hare. With competition among airlines, it’s easy to find a deal on a flight. The only real risk is a snowstorm shutting things down. But think about it: unpredictable weather can affect your flight anywhere in the world come winter. If flying still has you on edge, consider Amtrak, which serves Chicago with a dozen routes.
Food
Digging into this delicious mess will make you forget how cold it is outside (Corbis Images)
Nothing warms you up like deep-dish pizza. Beyond this Chicago staple, however, exists a culinary renaissance starring the likes of award-winning chefs Rick Bayless (Frontera Grill), Stephanie Izzard (Girl & the Goat), Paul Kahan (Blackbird) and Grant Achatz (Next Restaurant).
Related: The Ultimate Chicago Chow Down: Pies, Dogs, and Italian Beef You’ll Drool Over
In fact, Chicago recently tied New York City with the most AAA Five-Diamond restaurants (five). Not bad for a town better known for its artery-clogging pizza.
Seasonal events
With so many free and low-cost things to do, winter rivals summer as a great time to explore the city. Head to Millennium Park for ice-skating beneath a dramatic city skyline and the Cloud Gate, affectionately known to Chicagoans as “The Bean.” At night, the free Lincoln Park Zoo is great for its twinkling ZooLights extravaganza.
Museums
The Art Institute of Chicago is a great place to escape the cold (Vasenka Photography/Flickr)
Tuck indoors for culture that will blow your mind — and keep you warm. TripAdvisor recently crowned the Art Institute of Chicago the No. 1 Museum in the World. The Museum of Contemporary Art Chicago is the only North American stop for the critically acclaimed exhibition David Bowie Is, while the Museum of Science and Industry is hosting the Treasures of the Walk Disney Archives — a must for any Disney lover.
Related: Hold on to Your Deep Dish… Chicago is Full of New Art and Design
Theater
Chicago’s famous theater district (Foto4Lizzie/Flickr)
Chicago’s Theatre District test runs a ton of theater before it migrates to Broadway. For belly laughs, check out the Second City, a legendary comedy and improv theater that’s produced comedians such as Bill Murray and Tina Fey. You could catch a show featuring Saturday Night Live’s next breakout star.
Architecture
Enjoy a drink high above the city at the Signature Lounge (TheeErin/Flickr)
Home to the world’s first skyscraper, Chicago boasts a glistening, modern-day collection of architectural marvels that astound year-round. For a birds-eye view of Chicago’s skyline, take the elevator up to the 96th floor of John Hancock Center and have a cocktail at the Signature Lounge. Or test your nerves at the Willis Tower, where you can dangle 103 floors above city streets in a glass box called the Ledge.
Sports
Wear your craziest Superfans ‘stache to cheer on the three B’s: Bears, Bulls, and Blackhawks. Chicago buzzes with beer-soaked sports fever in winter. If you can’t score a ticket to Soldier Field (football) or the United Center (basketball and hockey), belly up to the bar at a Chicago pub to cavort with locals. Just don’t diss Ditka.
Related: WATCH: See the Secret Tunnels in Al Capone’s Favorite Chicago Bar
Lakefront Path
Last year’s most famous Polar Plunge participant, Jimmy Fallon (Corbis Images)
Bundle up for an invigorating walk along the 18-mile path that hugs Lake Michigan. With summertime bikers, rollerbladers, and runners absent, it’s a serene stroll full of the city’s best photography opportunities — especially around the Museum Campus and Olive Park. If you happen to be walking along North Avenue Beach on March 1, you’ll witness the Chicago Polar Plunge, an annual tradition where Chicagoans run into a frigid Lake Michigan dressed in costume, some in their skivvies. Last year, Jimmy Fallon was among the celebrities who participated, fully clothed.
Bragging Rights
You think this is brave? Try being a Cubs fan! (Getty Images)
“You survived Chicago in winter? You are so brave!” That’s the sort of reaction you’re likely to receive around the water cooler when you casually mention where you spent your winter vacation. Regardless of whether others think you crazy or courageous, do regale them with anecdotes that don’t linger on the weather — please. Not doing so would only perpetuate a travel blemish that this Chicagoan hopes to diminish.
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