Why Chicago is Worth a Winter Visit

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Deal Expert, Chicago
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As a warm-weather-loving North Carolinian living in Chicago, I get why winter may not — yet — top your list of seasons to visit the Windy City. But if you ask our Chicago-based deal experts, who’ve spent a combined 1200 combined winters here, now is actually an ideal time to come see us. Here, five reasons why.

The best restaurants are easier to get into

To the surprise of exactly no one who lives here, 2017 saw Chicago’s anointment as Bon Appetit’s Restaurant City of the Year.  And even before that, A-List reservations could be tough to get in summer. But in winter, everything becomes more accessible—from Michelin-starred meals to cozy corner cafes. In fact, for the foodies among us, the best time to be in the city is Restaurant Week (Jan. 26-Feb. 8), when dozens of Chicago’s best offer tasting menus at an affordable price.

And for the…spirited traveler, the bar scene is a draw unto itself. In fact, one of our local deal experts, Chris Vassil, contends that “the unique bars, lounges, distilleries and breweries are worthy of a trip on their own.” Our favorite spots to cozy up tend to involve fireplaces or rooftop fire pits, plus comfy chairs and sophisticated cocktails. Try the Chicago Athletic Association, which also has a luxe game room, Drumbar or Roof on the Wit.

If beer is more your bag, consider the Chicago Ale Fest Winter Edition on Jan. 20—a daylong ode to American Craft Beer in the Grand Ballroom at Navy Pier. Think 150+ brews, the city’s favorite food trucks and a DJ.


You’ll have world-renowned masterworks (practically) to yourself

Yes, you’ll find shorter lines and thinner crowds all over the city in winter, but the phenomenon is particularly noticeable at the famed museums, where you’ll now have blessedly unobstructed views of the marquee masterpieces, from Seurat’s A Sunday Afternoon on the Island of La Grande Jatte at the Art Institute of Chicago to the beluga whales at the Shedd Aquarium (and yes, on the basis of cuteness alone, belugas are masterpieces of the mammalian world). Not for nothing, you’ll be indoors…potentially for days if you also hit the Adler Planetarium and Museum of Science and Industry (both family travel favorites).

The music and theater scene heats up

Though perpetually vibrant, this aspect of the city really comes to life in wintertime, with venues large and small offering something to lure you in from the cold. Theatre Week—Feb. 8-18—brings specially priced seats ($30, max) to 120+ shows, and though the participating productions have yet to be revealed, know that everything from the iconic, percussive Blue Man Group to musical-of-the-moment Hamilton is in town. Plus, the Theater District hosts touring Broadway shows all winter long. Then, there are the local legends: the Steppenwolf Theater Company and the Goodman Theatre, both beloved for their original and thought-provoking plays.

If it’s a concert you’re looking for (or just a selfie!), see who’s playing at the Chicago Theatre, home to one of the nation’s most Instagrammed marquees. Entertainment Deal Expert Ann Guettler also recommends scanning the calendar listings for everything from the city’s historic blues clubs to its large arenas. The whole gamut attracts amazing talent all winter long.

This is an epic winter sport-loving town

And our office is no exception. In fact, we’d bet we’re as psyched as anyone about scoring this deal for tickets to Bulls games. Not that all local winter sports relegate you to spectator status: If you’re here on a sunny day, we recommend checking out the skating ribbon at Maggie Daley Park (open through the first week in March) and the rink at Lincoln Park Zoo.

It’s the best time to indulge in a little luxury

Because this is generally low season for the city’s high-end hotels, they offer deals on everything from room nights to dining. We particularly love taking advantage of the deals on spa days to treat ourselves and warm up after a chilly afternoon. We’ve rounded up our team’s favorites – and even scored discounts at the best spas in the city.

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