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Why Visit Chicago in Winter: Insider Reasons It's Absolutely Worth It

In a few months, I'll celebrate my six-year anniversary at Travelzoo, where I've edited over 50,000 deals to destinations from Bhutan to Boise. One skill I've honed over 250+ weeks? Spotting the hidden perks of off-peak travel. Here's my expert pitch for visiting Chicago in winter.

Enjoy countless free attractions—plus unbeatable deals saving up to 50%—making your trip affordable and memorable.

New Hotels Galore

In recent months, three standout hotels have opened to rave reviews: The Gwen, Freehand Chicago, and the Chicago Athletic Association. The Gwen, Starwood's first Luxury Collection property in the city, sits right off the Magnificent Mile. Freehand Chicago, an upscale hostel with private rooms, attracts global travelers and locals alike for its acclaimed Broken Shaker bar. The Chicago Athletic Association has earned top honors from GQ, Vanity Fair, Condé Nast Traveler, and Men's Journal, which dubbed it "America's best new hotel." Travelzoo members save up to 35% plus enjoy a $15 daily in-room dining credit.

Seasonal Activities

Ice rinks sparkle across the city, including one at Millennium Park and the innovative skating ribbon at Maggie Daley Park, which debuted last year.

Free Attractions for Holiday Savings

Chicago shines with no-cost gems perfect for winter. Warm up at the Garfield Park Conservatory, where the new site-specific art installation solarise: a sea of all colors (opened last month) delights visitors, and kids explore the free children's garden. For skyline views at dawn or dusk, stroll or jog the elevated 606 path—burn calories to indulge guilt-free.

Secure Prime Reservations

A little planning unlocks tables at Chicago's hottest spots. Check OpenTable.com now for New Year openings, like dry-aged prime ribeye at Bavette's or small plates at Girl & the Goat. November visitors can join the city's inaugural French Restaurant Week. Master local pizza-making with this exclusive Pizzeria UNO deal, or browse more restaurant offers here.

Catch a Show

Chicago ranks top three in Travel + Leisure's 2014 America's Favorite Cities for architecture and boasts a vibrant arts scene. Many Broadway-bound shows preview here with savings up to 50%. Favorites like "Blue Man Group" and "Million Dollar Quartet" endure as must-sees.

Lead photo by Blanscape / Shutterstock.com

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