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When I made this a few weeks ago, I used Canadian Club 12 year as my base (fairly mellow, medium rye spice in a mixed mashbill), which paired nicely with Jacob’s Creek Double Barrel Shiraz (Australian, and finished in whiskey barrels). It was definitely a full-bodied drink as a whole - the shiraz adding deep plum fruit and chocolate notes - I quite liked it. Whiskey-barrel-finished reds are pretty commonplace (but not all are equal) among many brands and varietals, but definitely experiment! My choices may not scream “New York” but if this drink is Chicagoan in actual origin anyways - well, whatever tastes great!