Visiting Chicago in Winter? Trust Us, It’s Worth It

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Deal Expert, Chicago
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In a few months, I’ll hit my six-year anniversary at Travelzoo. My best guess is that I’ve edited more than 50,000 deals to places from Bhutan to Boise. And of the skills I’ve acquired over these past 250+ weeks, none is stronger than this: finding the positive perks of going to places outside of peak season.

So here it is: my pitch to come to Chicago in winter.

We have lots of free things to do — plus deals to make things extremely affordable, with savings of up to 50% off.

New hotels galore

In the past few months, three hotels have opened to much fanfare: the Gwen, the Freehand and most notably, the Chicago Athletic Association. The Gwen is Starwood’s first Luxury Collection hotel in Chicago, and is right of the Mag Mile. Freehand, an upscale hostel including private rooms, draws an international crowd for its guests — and locals are flocking for the creations from the Broken Shaker bar inside. The new Chicago Athletic Association Hotel has been praised by GQ, Vanity Fair and Conde Nast Traveler; Men’s Journal calls it “America’s best new hotel.” Travelzoo members save up to 35% and receive a $15 in-room dining credit daily.

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Seasonal activities

Ice rinks dot the city, including one at Millennium Park, and the ice skating ribbon weaves its way through downtown’s Maggie Daley Park, which opened just last year.

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Extra cash for Christmas presents

One of the many things I love about my hometown is just how many attractions are available to everyone, at no cost. My favorite two? The Garfield Park Conservatory is the perfect spot to warm up and fog up your glasses during the cold winter months. A new site-specific art instillation called solarise: a sea of all colors opened just last month, and kids can roam free at the children’s garden. Head to the 606 elevated path for the best views of the skyline at dawn or dusk for a stroll or a jog so you can eat with abandon.

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Get a reservation

With just enough planning you can reserve a hard-to-nab table at some of the city’s most popular spots. Check opentable.com now for openings in the new year, and start looking forward to dry-aged prime ribeye at Bavette’s or the small plates at Girl and the Goat. For those coming in November, there’s the city’s first French Restaurant Week as well. While you’re here, learn to make pizza like the locals with this exclusive deal from Pizzeria UNO. Or find other restaurant offers here.


And see a show

In Travel + Leisure’s list of America’s Favorite Cities 2014, Chicago lands in the top three for architecture, but it’s also home to a thriving arts scene. Many shows do a test run in Chicago before launching in New York, with savings up to 50%. Long-standing shows, such as “Blue Man Group” and “Million Dollar Quartet” continue to be favorites.

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Lead photo by Blanscape / Shutterstock.com

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