Three Cities that Shine in the Winter

While temperatures might be low, visiting Boston, Chicago and New York City during the winter has its perks. Smaller crowds, for one. Skating under a city skyline is pretty great too. The forecast calls for a fun weekend away in these three cities, and here’s why.
swhwn-80053-new york skyline

Bostonshe430wn-160088-Boston Skyline Local Area at Sunset

The World Figure Skating Championships are headed here at the end of March, but the graceful sport is a favorite pastime all winter long at the Frog Pond, an outdoor ice rink in the nation’s oldest public park, Boston Common. Indulge in some fresh-made mac and cheese or Belgian waffles at the Frog Pond’s café before hoofing it over to nearby Cheers on Beacon Hill. Kick back with a beer in the cozy confines of this neighborhood joint formerly known as the Bull & Finch Pub, the inspiration for TV’s legendary sitcom “Cheers.” 
Stay toasty while soaking in 360-degree views of this historic city with a trip up Prudential Tower to the Skywalk Observatory. Photo ops abound from this 50-story perch overlooking Fenway Park, Harvard University, Hancock Tower and other landmarks that look especially lovely with a dusting of virgin snow.
Forget it’s winter for a few hours by taking a deep dive into the New England Aquarium. Watch an IMAX show and treat the kids to one of the aquarium’s behind-the-scenes offerings for an up-close encounter with harbor seals or Myrtle the green sea turtle. 
When the mercury drops, nothing hits the spot like the Polcari family’s brick-oven pies at Regina Pizzeria. Dig in at the original North End location, serving hungry Bostonians since 1926. 


wes1031wn-127858-Michigan Avenue
Start out at Millennium Park and make like the reigning NHL champs with a workout on the ice. Free skating lessons are held Friday through Sunday mornings at McCormick Tribune Ice Rink, where you can practice your moves in the shadow of the park’s beloved “Bean” sculpture through early March.
Take advantage of the lighter crowds and post-holiday bargains with a shopping spree on the Mag Mile, an inviting stretch of Michigan Avenue from the Chicago River north to Oak Street. There’s no shortage of stores to pop into if you get chilly along the way. Mark the calendar for March 12 when the river goes green — thanks to copious quantities of vegetable dye — in honor of St. Patrick’s Day and the annual parade. 
Pack on a pound or two with some piping-hot deep-dish pizza at Lou Malnati’s. Even in the dead of winter, it’s worth waiting outside in the inevitable long lines for a delicious morning treat from Doughnut Vault

New York City

Taking a bite out of The Big Apple can be a real bargain in winter. During the first three months of the year, the city’s average daily hotel rate is lower than any other time of year. 
Bundle up and head outdoors to trace a few figure eights on the country’s most famous ice rink at Rockefeller Center. If you’re feeling extra brave, shed those layers and join the Coney Island Polar Bear Club for a plunge into the frigid Atlantic — a long-standing tradition that takes place at 1 p.m. Sundays from November through April. A more comfortable way to enjoy the water: take a ride on the free Staten Island Ferry. Cuddle up by one of the boat’s picture windows with a beer or coffee and watch the city’s iconic skyline as you cruise by. 
Make tracks to Midtown to warm up at the opulent Russian Tea Room. Afternoon tea service includes an option for kids, who will get a kick out of watching the colorful fish on display in the restaurant’s massive, bear-shaped aquarium.
So forget the sunscreen, put on that puffy jacket and explore these winter wonderlands when they’re at their most magical. No matter how cold it gets, great cities never go into hibernation.

You might also like


Why book here?

When you book on, our hotel brand sites or SPG apps, you get more than a great room.

Best Rate Guarantee*

If you find a lower qualified rate** within 24 hours of booking, we’ll match it–and give you a 20% discount or 2,000 Starpoints®.

Earn Free Nights

Our sites and apps are the only places to earn Starpoints on hotel bookings.

Free In-Room Internet

Get free Internet when you book on, our hotel brand sites or SPG apps.

* The Best Rate Guarantee does not apply to taxes, gratuities, or any additional resort or guest charges or fees that may apply at SPG Hotels.
** Qualified rate means it satisfies all the Terms and Conditions of the BRG program including the required timeframe of receipt of the claim 24 or 48 hours prior to the standard check-in time.