Five Reasons to Visit Chicago This Winter

Chicagoans don’t let a little cold weather cramp their style. Outdoors or indoors, the Windy City revs up when the thermometer dips. From skating to sipping to celebrating, here’s how to join in the fun.

> Get your blood pumping: 

A twirl around Chicago’s beloved Millennium Park ice-skating rink makes for a lovely winter afternoon, surrounded by perfect views of the downtown skyline. Top it off with hot chocolate and snacks at ice-side Park Grill Café.

If you’re feeling a little shaky, hone your skills with free skating lessons from Friday to Sunday, one hour before the rink opens. Tip: The 16,000-square foot space can get crowded, so visit at non-peak hours to avoid lines.

Or, check out one of the city’s other rinks, like the new Alpine-style skating ribbon at Maggie Daley Park, where athletic skaters zoom through chutes among the pines, or the glamorous Peninsula Hotel Sky Rink, four stories above Michigan Avenue’s Magnificent Mile.

Children in town? They’ll love the outdoor ice at the Lincoln Park Zoo, next to the big red barn.

When the snow comes down, take a break from visiting museums for a bit of cross-country skiing or snowshoeing on the trails at newly restored Northerly Island—site of the city’s former downtown Meigs Field airport—in the heart of Chicago’s Museum Campus zone.

Equipment is available at the Northerly Island field house. Or, for intrepid post-snowfall urban skiing in the park and along the lakefront paths, rent cross-country skis at the Lincoln Park REI store.

> Unwind and imbibe:

Had enough hot chocolate? Try tropical-themed hipster hideaway Lost Lake in Logan Square, on the city’s northwest side, for cocktails by local mixologist Paul McGee.

Closer to downtown, follow the torchlights through the alley to Three Dots and a Dash, a lively underground tiki bar in the River North neighborhood.

And for a touch of Havana-style glamour, complete with rum-based cocktails, in a restored 1920s-era lobby bar, hole up at Sparrow, an intimate space on a quiet Gold Coast street just west of Magnificent Mile

> Refuel with the locals:

Get reinvigorated with comfort food from old favorites like romantic, palm tree-studded Le Colonial—where chef Chan Le (aka “Mama”) has helmed the kitchen since 1997—or Old Town’s atmospheric German-American Glunz Tavern, established in 1888, but renovated and re-opened by the original owner’s granddaughter and great-grandson in 2012.

In the Loop, the mahogany and brass details of Altwood, a seasonal American food and drink restaurant on the ground floor of the historic Reliance Building, have recently been enlivened with contemporary, whitewashed touches.

New instant Logan Square classics like Osteria Langhe for Piemontese tajarin pasta with seasonal white truffles and buzzy Fat Rice for Macanese specialties likewise satisfy stomach and soul.

> Hibernate in style: 

Chicago is in the midst of a hospitality boom, and a spate of historic buildings have been restored and renovated into new hotels. These are cozy places with communal gathering areas and plenty of options for eating, drinking, and even keeping fit in a clubby, warm ambiance updated with a splash of bright color, a dash of industrial chic or steam punk panache, or a swath of midcentury-style wallpaper.

The Chicago Athletic Association, a stately 1890s Venetian gothic landmark across from Millennium Park, includes five eating and drinking spots (There’s a Shake Shack on the ground floor!), 24-hour fitness facilities with a basketball court sporting the original Cubs logo, plus a recreation floor where you can down a beer while playing indoor bocce ball and shuffleboard before dining at tony supper-club style Cherry Circle Room.

In the happening West Loop, Chicago’s outpost of the Soho House–a London-based club-hotel–occupies the former Chicago Belting Factory with six stories of retro cool for the creative class. Hotel guests have access to the gym (with a professional boxing ring), the club floor for all-day drinks and food, and the 30-seat private screening room. Two casual—and open-to-the-public—restaurants, Pizza East and Chicken Shop, serve wood-fired pizza and spit-roasted chicken.

The Virgin Hotel Chicago is Richard Branson’s first hotel in North America and it’s tech-enabled in every way, from check-in to room service. Friendly touches abound, like when the bellboy offers you a (free) lift in the hotel’s red limo. And the rooftop lounge, Cerise, is a sweet spot from which to watch the snowflakes fall.

In good news for savvy budget travelers, Chicago hostels are not just for backpackers anymore. At the upscale Freehand “hostel-hotel,” housed in a classic 1927 building in the city’s River North art gallery neighborhood, both private and shared accommodations feature modern amenities. The community vibe is strong in the common areas, with a street-food-inspired menu and Nicaraguan coffee at Café Integral and handcrafted cocktails at The Broken Shaker developed by the award-winning mixologists behind Miami’s Bar Lab.

> Ring in the New Year:

Chicago’s first annual New Year’s Eve party, Chi-Town Rising, will take place along the city’s revived downtown Riverwalk on December 31, culminating in Pioneer Court (where Jean-Baptiste Point du Sable set up the city’s first trading post in the late 1700s) with a host of bands, events, and celebrity guests.

Near midnight, a massive, glowing Chicago star will rise 350 feet into the air as the countdown finishes with a fireworks display. Leave the dropping ball to New Yorkers. Even in the cold, there’s only one direction—up—in the Windy City.

Ceil Miller Bouchet is a travel writer and the author of a forthcoming memoir, The Bordeaux Diaries, about her year studying wine at the University of Bordeaux. Follow her on Twitter @CeilBouchet.