Chicago in Winter: 7 Ways to Avoid the Cold (& Have Fun)

Dec 15, 2015

While we admit that wintertime doesn’t seem like the most ideal time of year to visit Chicago, low airfare and hotel rates will have you thinking twice. If you can just look past the weather and pack your warmest jacket (and hat, scarf and gloves), we promise you can still enjoy Chicago while staying warm. How? Head indoors!

Travelzoo and Google Local Guides have partnered up to recommend top indoor things to do in Chicago when it’s cold outside. Also read through the end to find out how you can win $300 toward your next Chicago adventure!

The most obvious way to keep warm is to eat, amirite?

Head to Fulton Market District and select from a number of 4.5-star restaurants, rated by Google, to dine at. Local Guide Jacqueline Stoutin says the dishes from Girl and the Goat are “standing ovation delicious.” Top contenders also include Au Chevale and Publican.

Or warm up your belly the Chicago way, by stuffing yourself with deep dish pizza. Local Guide Raj Desai recommends Lou Malnati’s “The Lou,” which comes on a garlic butter crust, while Local Guide Juan Antonio Fuentes prefers Giordano’s, but recommends visiting the Prudential Plaza/Millennium Park location for a shorter wait.

Travelzoo also has a variety of top-rated Chicago restaurants to select from, and with savings up to 50% off, here.

Grab a drink!

Warm the soul with a drink from the 96th floor of the John Hancock Center on the Magnificent Mile. The Signature Lounge at the 96th offers a variety of wine or whiskey paired with views of Lake Michigan and the Chicago skyline.

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But if alcohol is not your thing, Mindy’s HotChocolate in Bucktown makes a mean cup of hot cocoa. From Mint to Mexican, Local Guide Megan Town says the hot chocolates are served with a “made-from-scratch marshmallow that really balances out the treat,” and Lara Poeppelmeier recommends the homemade doughnuts, covered in cinnamon, sugar, and served with raspberry jam, which compliments “perfectly” with your hot chocolate.

Visit a museum

A trip here isn’t complete without visiting one of the many fine museums and institutions. Consistently ranked among the best museums in the world is the Art Institute of Chicago. Local Guide Jessica recommends designating an ample amount of time to go through their comprehensive art collection spanning from ancient to contemporary and to take a free guided highlights tour for a “more interesting perspective.”

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Art lovers will also appreciate the Museum of Contemporary Art Chicago, dedicated to sculpture, video, painting and film. Save 25% on admission with Travelzoo’s deal. Or explore mind-boggling facts about our universe with 45% off a visit to the Adler Planetarium -- America’s first planetarium.

Shop the Magnificent Mile malls

Dodge the cold and shop indoors. Hop from mall to mall on Magnificent Mile where you’ll be sure to get your fix of retail therapy. 900 North Michigan Shops and The Shops at North Bridge boasts luxury brands and specialty shops, while the Water Tower Place sprawls eight levels of household name stores from Gap to Banana Republic. Local Guide Dave Seefeld recommends stopping by the Dr. Seuss art gallery on the second floor.

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Snuggle up at a good bookstore

Nothing says warm like cozying up with a good book. It’s all the better when you’re at a bookstore shelved with endless options. The steps are easy: head to one of our favorite bookstores (Myopic Books in Wicker Park, Quimby’s in Wicker Park, The Book Cellar in Lincoln Square, 57th Street Books in Hyde Park), stack up on your favorite titles and then find a corner to spend the rest of your day in. Happy reading!


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Treat yourself to a day of pampering

Because after all, you deserve it right? Chuan Spa at The Langham was named one of the Best Spas in Chicago by Travel + Leisure. Pamper yourself this winter with a spa package that saves 50% and includes a massage, fitness class, prosecco, chocolates, a robe to take home and more. Or head over to the AAA 5-Diamond Four Seasons Hotel for over 35% off a massage. Both deals include access to luxe spa amenities.

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Admire Chicago from the inside

Soar to the top of Chicago’s tallest building – the Willis Tower -- and see the Windy City from 103 stories above street level. Travelzoo’s offer saves over 20% on admission. The Skydeck’s Ledge has four glass balconies that extend 4.3 feet outside of the building and provide views straight down at the city 1,353 feet below. Afterwards, head down to the 67th floor, to the exclusive Metropolitan Club for a luxe dinner for two for $89 overlooking downtown Chicago and beyond.

A photo posted by Toby Mitchell (@_tobymitchell) on

What do you like to do in Chicago when it’s cold out? Are there any expert tips and suggestions you can share with us? Let us and our friends over at Google Local Guides know by leaving a review here.

Local Guides is a global recognition and reward program for creators on Google Maps — those who help others make more confident decisions about where to eat, shop and play. Every high-quality review you leave on Google Maps starting now through the end of the year will increase your chance of winning $300 toward Travelzoo, so get reviewing!

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