Logan Square cocktail bar Analogue serves two large fishbowls for $36 apiece. The #3 has rum, cognac, sherry and pineapple, while #5 is made with bourbon, ginger beer, black tea, honey and Angostura.
BIG Bar offers all their cocktails, like a mule with Bulleit bourbon, lime and ginger beer, in two formats—Big and Very Big. The Very Big cocktails start at $38 and go up from there, and can serve two or more people.
Chicago Athletic Association rooftop bar Cindy's offers an "apothecary service" that serves 20 people. The Grey Garden is a mix of vodka and creme de violette with tea and lemon, while the Kick in the Daisy is a spicy drink with ancho-infused tequila and watermelon juice. The drinks are $250 each.
The Dawson serves five cocktails in various sizes, from Botija Nueva No. 2, which serves 3-5 and has brandy, Grand Marnier and pomegranate for $48. The largest one, Octopus' Garden, serves 6-12 and is made with rum, cognac, strawberry, grapefruit and other ingredients, and costs $200.
Elle on the River offers a variety of punches—a single glass is $10, and you'll save some cash by bringing friends—a punch for 10 is $75 and a serving for 20 is $150.
Frontier offers three punches that serve up to six people, like the Raspberry Gin Buck, with gin, raspberry-basil syrup, lime and ginger beer. The punches are $55 each.
Fulton Market Kitchen promises three "Cocktails As Big As Your Head," which are $70 a pop. They serve 2-5 guests each, and range from Moscow Mules to mezcal margaritas.
The Jimmy's summer cocktail list includes three pitcher drinks that serve 8 and cost $65. The bourbon tea is sweet with a bite, the Hemingway daiquiri is tart and sour and the Pimm's cup is refreshing with ginger beer and gin.
Lost Lake has four large cocktails to share with others. The cocktails range from $25 to $45 and include Wave of Mutilation/A Fish Tank Needs Sharks, with dark rum and cinnamon, and the Lima Lima Scorpion Bowl with gin and passionfruit.
Nico serves three different cocktails in pitchers—a traditional Bloody Mary, Wake Up and Gin with canteloupe-orange juice and prosecco and the Sandia Fix with tequila, lime cordial and watermelon bitters. They're $55 a pitcher and serve 4-6.