Why Chicago is the Romantic Destination You’ve Been Looking For

XWHY Guest Post: Chicago Naitive Liz Kores, gives her view on why the Windy City is the perfect spot for a romantic get away.

Let’s be real, many of the world’s cities that are most popular for being romantic are a little played out in the romance department…

There’s no denying that Paris, Venice and Maui are stunningly beautiful places that set the stage for some good ol’ fashioned romancing. But consider the fact that those places are also packed full of other couples trying to engineer memorable moments, and this tends to lead to overcrowding and inflated costs.

But there are plenty of world class cities that aren’t quite so synonymous with romance, but offer just as much to couples looking for a romantic getaway that doesn’t include hordes of honeymooners.

Chicago is one such town – though you might know it as The Windy City or The Second City, Chicago is also one of the most vibrant and historic cities in the US and is the perfect setting for a love-filled trip.

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Summer is Sexy & Winter is Cozy

This is a town that really and truly has 4 different seasons and each one is romantic in its own way. In the summer, the city’s streets come alive with street festivals and outdoor concerts.  Dining and drinking moves outside to the hundreds of intimate patios, bustling sidewalks and expansive roof decks.

And when the weather turns colder, it makes being inside feel all the cozier – wandering around the Art Institute, drinking a hot toddy in a dark blues bar or getting a couple’s massage at a fancy spa is pretty darn dreamy on a snowy, Chicago day.  And don’t even get me started on ice-skating hand-in-hand at Maggie Daley Park amid the sparkling lights of the city skyline…

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Jaw-Dropping Views for Days

You probably think New York was the birthplace of the skyscraper, but that’s just not so; Chicago was the first city in the world to construct glittering towers that reached dizzying heights and it continues to offer visitors some of the best views and most noteworthy architecture in the world.

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Grab a drink at the swanky Signature Room Lounge for 365 degree views of the city and Lake Michigan from the 96th floor of the John Hancock.  Or take a stroll through a few of the oldest and most beautiful urban neighborhoods in the country, like the Gold Coast, which is home to Oak Street, a street full of picturesque brick townhomes that now house designer boutiques and 5-star restaurants.  And if the weather cooperates, don’t miss out on an architecture river boat cruise the likes of which match any romantic movie setting.

Chicago’s Got the Blues

Chicago is considered to be the world capital of blues music, which most would agree has got to be one of the sexiest music genres around. Sure, the songs tell tales of hard times and broken hearts but, for some reason, its soulful rhythm and vibe inspires dancing and good times.

Head to Chicago blues institutions like Blue Chicago, B.L.U.E.S., Kingston Mines or Rosa’s for nightly live bands that play the real deal. A couple cocktails and a little hip shaking will definitely put you and your better half in the mood.

Speakeasy Style

If your idea of romance is a dimly-lit speakeasy bar that pays tribute to the classy lounges of old and churns out distinctive craft cocktails, you’ll adore Chicago. The city is home to genuine old school joints like The Green Mill jazz bar, where Al Capone used to hang out.

But many new underground, Prohibition-era watering holes have sprung up in recent years as well. Several of them even have secret entrances that will definitely make you and your significant other feel like you’ve stepped back in time and right into a steamy old movie or a mid-century spy novel.

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Comedy is King

For many, the very best aphrodisiac is laughter and Chicago is arguably one of the funniest cities in the world. It’s where improve and sketch comedy originated, and it boasts dozens of comedy clubs, including The Second City theatre and school, where world-famous comedians like Bill Murray, Amy Poehler and Chris Farley got their starts.

The River AND the Lake

Nothing says romance like looking out over a beautiful body of water, your sweetie by your side. And Chicago has not one, but two bodies of water: The Chicago River that winds its curvy way through downtown and Lake Michigan, which is the 5th largest lake in the world and appears, for all intents and purposes, to be a glittering ocean backing right up to the very edge the city skyline.  There are even sandy beaches for summertime lounging.

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Acclaimed Cuisine

With every passing year, Chicago gains more Michelin Star restaurants and eateries headed up by James Beard award-winning chefs and rising stars in the culinary world. So, if the way to your honey’s heart is through his or her stomach, The Windy City is the ideal place for a romantic vacation.

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Try avant-garde favorite Alinea or sample the Italian cuisine of President Obama’s favorite chef, Tony Mantuano at Spiaggia.  And, of course, you’d be remiss not to sample some of the city’s local dishes like an deep dish pizza and Italian beef sandwiches.

Chicago certainly was Sinatra’s kind of town and, really, that should be recommendation enough to visit this romantic city. But if you won’t take Ol’ Blue Eyes’s word for it, take mine – The Windy City is nothing short of magical.

About the Author: Liz Kores is a fashion & culture blogger who loves sharing her passion for all things Chicago. She is also on the board of the Chicago Fashion Incubator and the managing director of Oak Street Chicago, an association of Chicago boutiques, spas, hotels and restaurants. Click here to learn more.



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