At some steakhouses, diners with the courage to finish a Flinstones-sized piece of beef get a prize and a free meal. The same should be offered to anyone who can down a 48-ounce martini or 2-liter beer boot, no? These monstrous cocktails pose the ultimate challenge, one we don't recommend taking alone.
Cocktail Size Matters: Prost
2566 N Lincoln Ave, Chicago, IL
If you dare to order the 2-liter 'Das' beer boot at this German beerhall, you better abide by the rule: Once you pick it up, don't put it down until it's empty. Drinkers' advisory: Do not operate heavy machinery.
Zocalo Restaurant and Tequila Bar
358 W Ontario St, Chicago, IL
It may be called Aguardiente, or 'firewater,' but this 28-ounce concoction housed in a clay cazuela bowl is deceptively sweet with its blend of Herradura Reposado Tequila, grapefuit, lime, pineapple and orange juices. Drinkers' advisory: Keep five Advil by the bed.
Rockit Bar & Grill
22 W Hubbard St, Chicago, IL
Maybe the last time you had a Bomb Pop was on your Schwin next to the ice cream truck. Well, this River North bar's red-white-and-blue beauty arrives in an erect, 14-ounce glass filled with Bacardi Raspberry, Bacardi Limon and other ingredients. A cherry topping and popsicle stick garnish completes the party. Drinkers' advisory: pre-bedtime omelette and four extra hours rest.
Pops For Champagne
601 N State St, Chicago, IL
You and your crew will be way beyond bubbly once you get through a magnum-sized bottle, worth about 1.5 liters of champagne. Drinkers' advisory: Trying to beat a hangover? Forget about it.
Big Bar
151 E Wacker Dr, Chicago, IL
This bar, and its martini, is for those who know that size really does matter. So when posed with the question, "Would you like your martini big ... or bigger?," know that the correct answer arrives in an eye-popping 48-ounce glass. Drinkers' advisory: Drunk dialing highly likely.
Ceres Cafe
141 W Jackson Blvd, Chicago, IL
A 12-ounce drink doesn't sound like too much to handle, unless of course, it's filled with pure alcohol. In order to make room for a mixer of their choice, patrons must suck down the poison first. Drinkers' advisory: That's worth about four airplane mini-bottles of booze.
Merkles Bar & Grill
3516 N Clark St, Chicago, IL
This Wrigleyville hang earns the prize for best barware. On game days, regulars imbibe Long Island Ice Teas and other specialty cocktails from 100-ounce fishbowls. Drinkers' advisory: Write your address down on your hand before you go out so the cab driver will know where to drop you.
Crobar Nightclub
1543 N Kingsbury St, Chicago, IL
Maybe The Graveyard is a sign of how you'll be feeling the next day. A few glasses of the pint-sized concotion of Bacardi 151, vodka, gin, triple sec, tequila, bourbon, scotch and beer will have you wishing for death. Drinkers' advisory: Likely to cause embarrassing private confessions or full-on PDAs.
Favorite Spots for Martinis and Manhattans in 
