Chicago got its famous Second City nickname way back when, but if you’ve ever spent time there – and certainly if you’ve come to fall in love with the place – you’ll know that it’s something of a misnomer. You’d be hard-pressed to find anything resembling an inferiority complex here, or anything in the way of runner-up status, in a city this grand, where there’s a majesty and sweep to the skyline and a general feeling among die-hard fans of the city that it is in fact second to none, thank you very much. This is a metropolis of steel and glass, working class neighborhoods, men in suits who fill the high towers, a city that’s built on art, dive bars and fine dining, with so many tributaries of commerce and human enterprise – and then there’s the booze.

Chicago, it turns out, is home to more breweries than anywhere else in the U.S. The chief economist of the Brewers Association told The Chicago Tribune in December that this is “a very versatile beer city.” Which is a fancy way of saying – if you love a great hole-in-the-wall, if you’re a connoisseur of the perfect brew, a denizen of fine drinking establishments who has warmed your fair share of barstools and cocktail lounge seating in your day, then Chicago just might be a booze-lover’s idea of paradise on earth.

Here, without further ado, are a few of our suggestions of bars and drinking spots worth passing through if you ever find yourself with time to kill in Chicago:


Regarded as one of the premiere tiki bars in the country, this cocktail hideaway offers visitors a tropical-themed drinking spot found through a back alley in Chicago’s trendy River North neighborhood. It’s decorated with kitschy touches like skulls and a hut theme, and the menu features tiki cocktails prepared with fresh fruits and spices, along with delicious rums and distilled spirits. Juices and elixirs are cold-pressed and prepared in-house daily, making this memorably named establishment the perfect way to get a taste of the tropics without leaving the big.

435 N. Clark St.; @threedotsandadash/