Signature Sunset Ice Cream at Bobtail Ice Cream Company
One of a handful of always available flavors at this Lakeview ice cream shop, Signature Sunset is a genius combination of Merlot ice cream and dark chocolate chips. Just like the real thing, the Merlot base carries hints of berries and plums that provides a strong backdrop to the shards of premium dark chocolate, making for one variation of red wine that you'll want to devour all summer long.
Spiked Milkshakes at 25 Degrees
If you want a spiked milkshake that looks like it'll politely shake your hand but then pulls you into a fierce bear hug when you get too close, go for the Salted Caramel. Maker's Mark bourbon is by far the dominant flavor, but it blends well with the sweet vanilla ice cream, butterscotch, and sea salt sprinkled whipped cream. If, on the other hand, you want a milkshake that smiles sweetly at you and blows a liquor-scented kiss, the Bananas Foster is the one. The ying to the Salted Caramel's yang, this milkshake is more subtle in every way. It's sweeter, there is likely a little less of the featured liquor (rum in this case), and there are just hints of the supporting vanilla and banana flavors.
Jameson Soft Serve at The Boiler Room
For the true whiskey-lover, this velvety soft serve is ideal if you've ever thought to yourself: "This shot of Jameson is great and all, but what would really make my day is if it were just a tad sweeter and I could eat it with a spoon."
Butterscotch Bourbon Pecan Gelato at Black Dog Gelato
The Butterscotch Bourbon Pecan gelato at this young Chicago legend has the trademark soft and creamy texture, interrupted only by whole, perfectly toasted pecans. The tasting experience is exceptional, akin to slowing down the bourbon-tasting process. The first thing that hits you is the silken texture while you wait for the flavor to arrive. Then you'll discover subtle sweet vanilla and caramel flavors, followed by the lightest burn of whiskey, which slowly builds to a smooth finish.