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Sleepless in Chicago: 5 Ideas for a Romantic Date

You’ve already fallen in love with the Windy City, but now you’re head over heels for a pair of windy eyes too? Chicago boasts numerous opportunities for lovebirds new and old, so just calm your heart and the rest will follow.

As for your first romantic date here, these are our top picks.

  1. Chicago Botanic Garden

Let the story of your first kiss start at the Chicago Botanic Garden, where meandering lanes and secluded benches set up an amazing scenery in spring and autumn alike. This fall, take your date for a picnic there and smooch your way through red and yellow foliage.

  1. Ice Skating at Millennium Park

For your own moment of serendipity, pay a visit to the Millennium Park’s McCormick Tribune Ice Rink. Drink some mulled wine, hold hands, and try pirouetting on ice. The beauty is – even if you fall, you’ll have someone to catch you in their arms.

  1. Romantic Getaway for Two

Alternatively, skip the town and drive off to the outskirts of the city. Book a room for two in a romantic hotel in Illinois and spend a weekend sipping champagne. It’s a perfect way to get to know each other away from the prying eyes.

  1. Green Mill Cocktail Lounge

Fall in love while dancing at the Green Mill cocktail lounge, a swank jazz joint at the heart of Chicago. This smoky spectacular place was once a hangout of Charlie Chaplin and Al Capone, but now hosts local swing musicians and slam poets.

  1. Christkindlmarket

November in Chicago is in full swing, with amazing open-air markets popping around every corner. Christkindlmarket may just be the best for an aimless romantic walk, as it traditionally offers Glühwein, a hot spiced wine certain to melt your hearts.

Enjoy falling in love in Chicago and see you in time for Valentine’s!