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TRAVELER NOT TOURIST | 18 February '19
And one thing you definitely *shouldn’t* do.
Ahh, Chicago—one of America's great cities, and a place that's sometimes colder than Antarctica. Luckily, the hardy people of this frozen wasteland have figured out excellent ways of entertaining themselves in their frigid hometown. And while I’d prefer to go in a livable month like May, somehow I find myself in Chicago every January. Here are seven of my favorite ways to beat the cold:
If you're already hitting some tourist hotspots, the Chicago Athletic Association, just a block north of the Art Institute, is a great place to take a break and warm up. Don’t let the name fool you—the CAA reopened as boutique hotel a few years ago. The Drawing Room (also known as “the lobby”) has comfy leather seats and roaring fireplaces that give it a Hogwarts vibe, made all the better with the superb craft cocktails on offer. Feel like a change of scenery? No need to go back outside. Head behind the front desk and check out the Game Room, which has shuffleboard and bocce courts, a good beer selection and elevated bar eats. And keep venturing farther back to find the Cherry Circle Room, a posh cocktail bar and fine dining destination with a sexy, mid-century vibe. Any one of these spots alone would merit a place on this list, but the fact that you don’t have to step foot outside to go between all three make them a wintertime must.
Cold weather is a fantastic excuse to sample each of the more than two-dozen vendors at the Chicago French Market. This popular food hall predates its Italian competitor Eataly by a few years and isn't quite as devoted to the theme—the emphasis is more on ‘local’ than ‘French.’ Sample everything from Parisian crêpes to Chicago-style hotdogs, and have a bubble tea to wash it all down.
This Wicker Park institution is so much more than a used bookstore. Myopic Books has more than 70,000 volumes for sale, so even picky readers can find something they're into. With live music and poetry readings, it’s also a cultural hub of the local community, so there's plenty to do even if you somehow get tired of browsing the endless shelves.
Tourists keep comedy mecca The Second City a consistently hot ticket, but The iO is truly the home of Chicago's best improv and sketch comedy. Plus, with four different stages inside their new space, you can spend a whole night seeing headliners and up-and-coming acts under one roof. Keep an eye out for when TJ & Dave are in town—it's the best improv show in the country.
"Good British Food" sounds like an oxymoron to some, but if there's one thing the Brits are good at it's food that will warm you up (read: tons of mashed potatoes). The Red Lion Pub's menu offers all the British classics, like their craveable full English Breakfast and Shepherd’s Pie. And if that doesn't help thaw you out, their space has three—yes, three—fireplaces.
One of Chicago's premiere jazz spots, this old speakeasy has live music seven nights a week. Listen, everywhere in Chicago is heated, but between the decades of history, the lively bar and some of the best jazz in the world, fewer spots have more warmth. At the Green Mill you won't have to worry about a venue change as the night goes on—the music just gets looser as the scheduled acts give way to impromptu jam sessions in the wee hours. Plus, if you're really freezing, you can warm up by sneaking into the Prohibition-era tunnels beneath the bar (don't actually do this, it's definitely against the rules).
"The Cold?" you ask, "Hah! I laugh at the cold! The cold means nothing to me!" Ok, you’re being weirdly aggressive about weather—but if you insist, you can try your hand (and broom) at the Curling rink at The Gwen Hotel's rooftop bar. Plus, once you realize you aren't immune to frostbite, you can warm up under their heat lamps and fire pits (with a Hot Toddy for good measure). The view of River North is pretty fantastic, too.
Just kidding—this is a terrible idea.
Whether you want to embrace the chill or escape it, we've got you covered with the ultimate winter travel guide.
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