Why it rules You can actually taste the tequila you’re paying good money for instead of a watered-down version of it, plus you get more for your money since there’s no ice taking up room in the glass.
Why it blows It’s impossible to keep cool on a hot day, unless you’re an alkie who slams your drink before it has time to warm.
Where to drink it The Spanish margarita ($12) at the Violet Hour(1520 N Damen Ave, 773-252-1500) earns its name by subbing the citrusy vanilla liqueur Licor 43 for triple sec and adding a splash of bitters to balance the sweetness. The only alterations the Matchbox(770 N Milwaukee Ave, 312-666-9292) makes to its impeccable take on the classic is a touch of egg white for froth and a powdered-sugar rim ($8). —Heather Shouse
ON THE ROCKS
Why it rules It’s cold from the first sip to the last, and it’s the style nature (okay, bartenders bent on authenticity) intended.
Why it blows If you’re sitting outside or just can’t keep your hands off your cocktail, that ice will melt and water down your ’rita.
Where to drink it Frontera Grill(445 N Clark St, 312-661-1434) sets the standard for margaritas on the rocks. You can go in a dozen directions, but we love the tamarind version, which gets a kick from a hint of chipotle ($10).—Heather Shouse
Why it rules Unlike machine-made margaritas, there’s actually a chance the blended kinds are made with real lime juice rather than crap mixes, making it fresher-tasting without sacrificing the trashy satisfaction of drinking a frozen alcoholic beverage.
Why it blows Good luck finding one—the vast majority of margaritas denoted as “frozen” come out of a machine. And if you do get your hands on one, there’s still the risk that the ice won’t be evenly blended, leading to chunks hiding out in the glass.
Where to drink it If all you’ve had is the premixed frozen variety, El Cid(2645 N Kedzie Ave, 773-395-0505) takes it to the blender ($5–$9).—Julia Kramer
Why it rules It tastes like a slushie and goes down easier than a glass of water.
Why it blows The brain freeze! The sinus freeze! The splitting, numbing headaches! The total humiliation of ordering one and getting snickered at if the place doesn’t serve them! Not to mention the fact that the vast majority of them are sickly sweet, watery and just plain sucky.
Where to drink it The South Loop restaurant Zapatista(1307 S Wabash Ave, 312-435-1307) does competent versions of frozens ($8), plus the food far surpasses other frozen-margarita destinations.—Julia Kramer