Earlier this week I had the pleasure of taking a quick jaunt out to Chicago.  It was a good time to see the city as the weather was crisp and pleasant and the mood frenzied, with buildings and people festooned in Cubs gear (sorry to bring it up folks).  Anxious to try out some cocktails but not having much experience on the ground, I turned to the trusty Imbibe Magazine, for the hottest bars.

Boy did it not let me down, sending me to two wonderful bars: the historic Chicago Athletic Association Hotel (CAA) and the Bay-Area themed Presidio.  The CAA is a massive 1890s Gothic sports club restored as a stately boutique hotel. It is the epitome of immersive, with every facet of the complex–including a truly beautiful bocce court–lovingly refurbished.  The building has four bars, each one of them warm, welcoming, and beautiful.  You can read more about CAA’s history at their excellent website here.  And it has a Shake Shack!

So after a few pre-game Schlitzes in the Game Room bar (it’s Chicago!), I got to work in the Cherry Circle Bar, home to a truly cool vibe.  After being warmly greeted by the superb bar staff, I started with the “Old Cuban” made of rum, lime, mint and champagne.  This was a very simple, up-front drink with a nice mint flavor on the edges.  It’s also a generous pouring, so a proper starter, I thought, for a long session. Then I jumped to the “Turf Club” with gin, dry vermouth, maraschino, orange bitters, and absinthe – a very exciting ingredient list.  My anticipation was slaked as this was an excellent drink, unfolding slowly with a chilly hue that bites but doesn’t kill.  Very enjoyable.

My second half at the Circle started with the aggressive “Toronto” with rye whiskey, demerara, and fernet.  This is in your face rye but not overly offensive, as long as you slip slowly. The fernet also plays nicely, adding an almost citrusy tinge.  My time at the CAA ended, sadly, with a “Bizzy Izzy Highball,” made of bourbon, sherry, pineapple, lemon, and soda – this was an easy drinking experience with the pineapple notes playing nicely off of the strong, earthy bourbon.  Sweet and refreshing.

From Victorian club life I jumped to the hip environs of modern San Francisco. Presidio is a stylish venue in the Bucktown neighborhood that promises good drinks and a light, Golden State-influenced menu.  With helpful and fun bartenders, extremely creative and daring drinks, and a relaxed atmosphere, the establishment delivers on all counts.

I started with the “Stirred Byrd” made of pineapple infused rum, blackstrap rum, bitter liquer, citric acid, and lime.  Wow, this was a really intriguing flavor, very butterscotchy with an almost caramel sensation.  This wasn’t my favorite but I give it high marks for creativity and unique flavor.  Next up was the “Civil Disobedience” with vodka, Jamaican rum, cranberry, vermouth, and nutmeg.  With the cranberry and nutmeg, the Disobedience was extremely rich and flavorful on the front end and had a great and full taste through and through.  Enjoyable and refreshing, this complex mix was my favorite drink as Presidio.

I got downright giddy when I read the ingredients for the “California Derby” which included Cognac, White Port, Bourbon, Apricot, Toasted Cinnamon, Grapefruit, and Tiki Bitters.  Sounds magical, doesn’t it?  The follow-through was there in a very unique taste, nutty, with a subtle, warm, almost all-spice taste to it.  A nice creamy taste for a fall evening.  The end of tour drink was the “Sweater Season,” with sherry, scotch, spiced chamomile cider syrup, lemon, dried apple, and grated cinnamon. I didn’t quite love this one as I found the apple syrup heavy and strangely stringent.  The mix didn’t quite work for me.