From the book Shaken Not Stirred: A Celebration of the Martini, I’ve culled the following Chicago-related tidbits:
A “Chicago”-sized martini is a whopping 8 oz., double that of a large (or “boardroom”) martini. (p. 12) Chicago is famous for it’s “more-than-generous double-sized drinks, served in birdbath-sized cocktail glasses…”. (p.105)
Serve it “superlatively dry,” a la the martinis served on the Twentieth Century Limited train from New York to Chicago before WWII. (p. 48)
Doug Varnes at Chicago’s Set 'Em Up Joe “‘polishes’ his double Martinis with a light vermouth spray.” (p.55)
Kimon of Chicago’s Lion Bar serves up “smoked” lemon peel twists with his Martinis, holding the peel two or three inches over the glass and twisting it after lighting the match, giving the peel an expert twist. If you do it right, you’ll get a little flame and puff of smoke; promptly drop the peel into the drink. The peel must be fresh and should have “just a touch” of the inner lemon attached, not just rind. The author recommends you enlist a friend to hold the match, at least while you’re learning the technique. (pp. 82-3)
The Chicago Blue Martini (at Set 'Em Up Joe): 3 oz. Tanqueray Sterling Vodka and .5 oz. Blue Curacao. (p.91)
On chocolate Martinis: “When we recently visited the Windy City, we discovered… [a] chocolate Martini lover’s heaven. (Maybe it’s the aroma of Milk Duds wafting from the Holloway Candy Company production plant near the downtown area…).” In this town, the choco Martinis are often served with cocoa-frosted rims and Hershey’s Kisses for garnish, although other candies are used (Tootsie Pops and Tootsie Rolls), as are fruit and nut flavorings. A good side dish to serve with these drinks are strawberries and Godiva chocolates… and “to brighten the flavor of the berries, [cut off their tops and] stand them cut side down in a tablespoon or two of balsamic vinegar.” (pp.105-6)
Jerry Langland’s Double Chocolate Martini: equal parts Stoli Vodka, Godiva Chocolate Liquor, and Kahlua or Bailey’s Irish Cream.
Langland’s Mixed Chocolate/Chocolate Swirl: the above, but substitute Godet White Chocolate Liquor for the third ingredient.
The Chocolate Kiss (at Set 'Em Up Joe): 3 oz. Tanqueray Sterling Vodka, .5 oz. Bols Dark Creme de Cacao, 1 dash heavy cream, and a Hershey’s Kiss for a garnish.