Maker’s Mark–laced salty caramel shake at 25 Degrees

There’s no finer way to drink in the bliss of a fleeting Chicago summer than through a straw in a thick, velvety milk shake. This shake season, we couldn’t help noticing how chef-driven creations have transcended the traditional fast-food varieties (which we still love all the same). In search of the best, most creative, and most outrageous shakes out there, we sipped and slurped all sorts of frozen goodness to bring you this list, tailored to the type of liquid indulgence you seek.
 

HIGHBROW
Those with discerning taste buds seek out Allium, where the Four Seasons’ pastry chef Scott Gerken handcrafts shake ingredients. His repertoire features three ultracreamy options: two rotating picks (currently peach Melba and caramel popcorn) and the mainstay, miso butterscotch ($5), anchored by Homer’s vanilla ice cream and swirled with a rich butterscotch sauce that contains actual miso paste. The result is 14 ounces of ambrosia, which Gerken says is meant to be shared. We say otherwise. Four Seasons, 120 E. Delaware Pl.; 312-649-2349

TOTALLY INSANE
If you prefer your frozen treat fully loaded with housemade baked goods, break out a spork at BadHappy Poutine shop. You are already sabotaging your diet so you might as well go gangbusters with a shake ($5 for 12 ounces). Packing a whole slice of yellow sheet cake and littered with rainbow sprinkles (which unfortunately settle at the bottom), the oddly lumpy birthday cake shake is your ten-year-old self’s nirvana. Ditto the chocolate and peanut butter one, which boasts chewy chunks of flourless chocolate cake. 939 N. Orleans St.; 312-890-2165

DIY
If you long for a plethora of flavors, peruse the selection at Choppers—the perfect spot to unleash your inner shake chef and combine the 15 options into endless iterations. Coconut mocha Oreo? Why not! According to owner George Mavraganis, the key to his spoonable frozen treat is twofold: a soft-serve ice-cream base with a higher-than-normal butterfat content, and real ingredients. These include apple chunks cooked with cinnamon, cloves, and brown sugar to taste surprisingly like apple pie, and strawberries, which are blended with creamy peanut butter for the nostalgic PB&J (both $3.39 for 20 ounces). 1659 N. Ashland Ave.; 773-227-7800

SECRET
If you get off ordering off menu, flaunt your insider credentials at Edzo’s, and try the Speculoos (made with a gingerbread-tasting Belgian spread), the Elvis (peanut butter, chocolate, and banana), or the Mudslide (Oreo and coffee). The secrets aren’t tough to uncover, nor are they meant to be (a jar of Speculoos sits atop the blender). In fact, owner Eddie Lakin freely divulges all the details about his fabulous 20-ouncers ($4 to $5), from ingredients (no-frills Kemps vanilla ice cream) to his secret weapon for creaminess (a slow-blending spindle machine). 1571 Sherman Ave., Evanston; 847-864-3396

BOOZY
If you’re looking for a buzz, tip one back at the River North burger bar 25 Degrees. The 16-ounce spiked shakes satisfy both the desire for alcohol and the craving for a creamy grease-soaker-upper in one malt-shop-style glass. All eight concoctions are enticing, but the best we tried was the Maker’s Mark–laced salty caramel ($10). Although standard vanilla Häagen-Dazs serves as the base, a speckling of Hawaiian red sea salt (made ruddy by volcanic clay, which also imparts a subtle earthiness) and a streak of housemade butterscotch add pizzazz. Bottoms up! 736 N. Clark St.; 312-943-9700

Photograph: Anna Knott