A Winter Walk Around Chicago: What to Do and See

by  Laura Motta | Feb 24, 2015
Chicago / Sean Pavone/iStock

Why would you visit Chicago in the winter? Before you balk, or proclaim that the city is simply too cold for sightseeing before June, hear us out. The windy city lives up to the moniker in February or March, but a visit in the coldest months can reveal the friendliest, least crowded, and most affordable sides of America’s second city. We visited in January, courtesy of Hilton Hotels and their incredibly affordable Chillcation package, and experienced it firsthand. So bundle up and follow our advice for a stimulating, brisk walk around downtown Chicago…


No matter your tastes, whether you’re into stately neoclassical, '60s mod, or swooping steel-and-glass, Chicago has an architecture style for you. And if you’re happy to gawk up at all of the above, it’s a feast. Stop into The Rookery, one of the most iconic structures by World Exhibition designers Burnham and Root, for a tour of the lobby ($7), which was given a gold-and-glass update by Frank Lloyd Wright in 1905. For a free glimpse at an architectural marvel, stop into the Chicago Cultural Center. The space not only offers programs and classes throughout the year, the building’s showpiece is a swoon-worthy Tiffany glass dome -- the largest in the world. For more modern trappings, snap photos of the famous “corn cob” towers, more formally known as Marina City, situated right on the Chicago River, then warm up by the fire in the lobby of the nearby Raddison Blu at the Aqua. The exterior by architect Jeanne Gang, with its irregularly shaped balconies, is a geometric feast for the eye, and the hotel lobby has a coffee bar and a sleek gas fireplace that spans the length of the room. Be sure to pop into the expansive lobby of the Palmer House Hilton, with its brilliantly frescoed ceiling by French artist Louis Pierre Rigal. Have a drink at the bar, but be sure to stop at the Monroe St. entrance for a glimpse at the gilded “peacock door” -- another scrolling Tiffany confection that dates back to the days when there was a fine jewelry store in the building.


Shopping in Chicago is so much more than basic retail therapy. Some stores are experiences unto themselves, whether you’re looking to spend your money at the biggest chain stores on the planet, or in intimate, rigorously curated boutiques. In the heart of the Loop, you’ll find a Forever 21 that’s so big it looks more like a car dealership from the outside than a clothing store. There’s also a Bloomingdale's that focuses only on home goods and is situated in a restored Moorish revival theater called the Medinah Temple that dates back to 1912. As you browse top-of-the-line espresso makers or pick out your wedding pattern, pay a visit to the upstairs restrooms, of all places, for an up-close view of the theater’s original stained glass. If that’s not enough history for you, stop into Macy’s on State Street -- the site of Chicago's original Marshall Field's department store -- and look up at the Tiffany glass mosaic that glimmers on the arched ceiling. For a lower key, but no less interesting experience, head to P.O.S.H., a small shop on State St. on Chicago's North Side, that offers a discerning collection of new and vintage items from dishwear to jewelry to soap. Think of it as an independent, more-interesting Anthropologie.

Art & Activities:

Green Sawfish at Chicago's Shedd Aquarium from ShermansTravel on Vimeo.

What better way to stay warm than with a walk through one of America’s top art museums? The Art Institute of Chicago’s impressionist collection ranks among the best in the world, and its new modern wing, which opened in 2009, is as elegant and boundary-pushing as the art it houses. For a free glimpse at what’s quickly becoming one of the most recognizable pieces of public art in America -- and also a glimpse at your own smiling reflection -- pay a visit to Cloud Gate, affectionately known as "the bean," in Millennium Park by artist Anish Kapoor. Often snow-covered in winter, it welcomes selfie-snapping visitors 365 days a year. Among Chicago’s other top-tier museums -- although it’s not located downtown -- our favorite besides the Art Institute is the Shedd Aquarium. Watch white beluga whales swoosh by, spy long-nosed paddle fish, and even see shark eggs waiting to hatch. Another way to keep toasty is to get moving. The ice rink at Millennium Park is a surprisingly cozy way to spend an afternoon or evening. Skate rental costs $12, but you can’t put a price on the romantic winter atmosphere. Note that daytime skating offers fewer crowds, while the rink fills to capacity in the evenings.


Two things we love about Chicago food -- besides deep-dish pizza? Nearly every restaurant has a more-than-decent chicken soup on the menu and boots and sweaters are welcome attire in almost any establishment. For a laid-back lunch or a snack near Millennium Park, head to The Gage. With affordable pub fare and an excellent beer selection, it’s perfect for a post-sightseeing -- or post-skating -- break. If you're famished after hours of shopping on the North Side, stop into the newest outpost of Mario Battali’s Eataly for fresh mozzarella, oysters, or even craft beer. The Italian food mega-space feels right at home among the outsized stores in the area. For dinner, nothing feels quite as iconic as Park Grill, which serves new American fare with views of Millennium Park. And if you need a quick warm-up, our favorite coffee in the city is at Dollop.

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