Are you thirsty enough to take on our ultimate drinking to-do list? Some of the drinks features here are signatures that have become synonymous with the bar or restaurant that serves them. Others are just so delicious they've earned legendary status around the RedEye newsroom. From sweet to sour to downright boozy, there's a little something for everyone. Cheers!
1. Margarita ($8.50) at Matchbox
Ready for a 'rita that will knock you off your barstool? The boozy version at this teeny-tiny cocktail bar-served in a martini glass rimmed with powdered sugar instead of salt--makes margs on the rocks look like they're for sissies. -Lisa Arnett
2. Rosa ($5 for a 14-ounce pour) at Revolution Brewing
This hibiscus ale is a quintessential summertime sipper with a slightly floral flavor and an orange-derived tartness. Look for it in cans this summer as well as on draft at Revolution's Logan Square brewpub. -Kate Bernot
3. Pisco sour ($11) at La Sirena Clandestina
The next best thing to a South American vacation (seriously), this Fulton Market restaurant's pisco sour is a refreshing and lightly frothy combo of Peruvian pisco, bitters, lemon juice, egg white and just a bit of sugar. -KB
4. Dulce de leche licuado ($4) at Big Star
I'm never patient enough to wait for a table at Big Star to drink cocktails, and that's OK. Why? Because I can still get the dulce de leche licuado from the walk-up window, and, my god, it's the best milkshake in the neighborhood. --Jessica Galliart
5. Sherry ($6-$28) at Vera
If you think sherry is only for grannies, a trip to this Spanish-inspired West Loop restaurant will change your mind. Sherries shine the brightest when sipped with food. The staff here expertly pair all different styles of this fortified wine that hails from the Jerez region of Spain (and yes, if it isn't made in Jerez, it isn't sherry by definition) with just the right dishes. -LA
6. Chilled drinking chocolate ($7) at Katherine Anne Confections
The hot chocolate at this Logan Square shop is a seriously indulgent winter warmer, but-sorry Katherine Anne!-I don't want to touch it with a ten-foot pole when it's sweltering outside. Flavors for the summer season range from salted caramel to malted milk to chai. -LA
7. Italian sodas ($2.75) at Cipollina
Hot days spent shopping in Wicker Park necessitate these fizzy coolers made with locally produced Jo Snow syrups in creative combos such as grapefruit-rosemary, tangerine-lavender and hibiscus-basil-orange. -KB
8. Nutella milkshake ($4 at Lincoln Park location) at Edzo's Burger Shop
Generous scoops of Nutella and ice cream are mixed by a retro-cool Hamilton Beach mixer, then topped with the requisite whipped cream and cherry. Bonus: You can slurp up every last bit from the metal mixing cup served along with your shake. --KB
9. Bubble tea ($3.15-$4.05) at Saint's Alp Teahouse
No summer stroll through Chinatown is complete without a bubble tea break at this tea shop. Flavors range from classic green tea to peanut to sesame, though I'm partial to the coconut milk tea. -LA
10. Aguas frescas ($2.50 for a 12-ounce glass) at Antique Taco
Here's your mini-Espanol lesson for the day: aguas frescas translates to "fresh waters." At this cute-as-pie Wicker Park eatery, that means water flavored with sugar, lemon juice and whatever pureed fruit is tasty and in season. When watermelon rotates in, I'm a happy camper. You can even order 'em spiked with vodka if you're in the cocktailing mood ($12 a pint; $23 per pitcher). --LA
11. Moscow mule ($9) at Homeslice
Plenty of bars make a fine version of this classic vodka-lime juice-ginger beer concoction, but there's just something about this one-maybe it's the charming Russian Standard copper cup that it's served in--that makes you want to order another round and another round. --LA
12. California egg cream ($8) at California Clipper
I can't go to this Humboldt Park bar without ordering this vodka-spiked spin on the classic soda fountain drink, made with cream, soda and dark crème de cacao liqueur (and confusingly, no eggs). If you don't do dairy, go for the Purple Martin, a coconut rum drink that that showcases the amazing fact that the Clipper has grape soda on its bar gun. -LA
13. Daiquiri ($10) at Billy Sunday
Cane sugar rum and overproof rum add oomph to this Logan Square bar's take on the tropical staple. Lime, passion fruit and pineapple bitters are balanced, not overly sugary-and there's nary a plastic umbrella in sight. -KB
14. Peanut butter and jelly martini ($8) at Blue Line Lounge and Grill
This might not sound like a flavor combination you'd want to consume in liquid form, but trust me on this one. It's frothy, sweet and quite like a PB&J. The best part is they're only $5 on Wednesdays. -Leonor Vivanco
15. Swirl margarita ($8.50) at Uncle Julio's
Yeah, I went there. This cheesy Tex Mex joint's signature drink is exactly what you get when frozen sangria mixes with a frozen margarita. Don't be ashamed. Just order it. -Jessica Cantarelli
16. Smokey violet smash ($14) at Maude's Liquor Bar
You can't go wrong ordering any cocktail here, but the smashes-with their crushed ice and lovely mint leaf garnishes-are a signature. You can order 'em with vodka, gin, whiskey, rum or chartreuse, but I prefer the smokey violet version for its herbal flavor and purple hue that lightens as the ice melts. Don't say I didn't warn you: The price adds up quick for how quick these go down. --LA
17. Iced coffee ($3.25) at Bow Truss Coffee Roasters
The house-roasted varieties at this local coffeehouse (with locations in Lakeview and River North) are even more of a morning wake-up call when served on ice. --LA
18. Orzata float ($3.29) at Medici on 57th
Sure, you can get a classic root beer float at this Hyde Park café. But why would you do that when you can order this dreamy concoction made with almond soda and a scoop of chocolate ice cream? --LA
19. Negroni slushy ($8) at Parson's Chicken & Fish
On opening weekend, this recently opened eatery had diners clamoring to get their hands on this hybrid of a Slurpee and the negroni, a classic cocktail traditionally made from gin, vermouth and Campari or other Italian bitters. You'll find it stirring in the frozen drink machine behind the bar. --LA
20. Mango lassi ($3.25) at Uru-Swati
Smoother than a milkshake but not quite as thick as a smoothie, this blended yogurt drink is just the thing to cool your tastebuds in between bites of spicy curry. -LA
21. Horchata martini at Late Bar
When this Avondale bar opened in 2009, it's late-night license was the primary draw; however, it didn't take long for this spiked version of a taqueria favorite to become a signature. Not to leave vegans out of the fun, there's a soy milk version available, too. -LA
22. Spreetz ($12) at Bar Toma
Drink like the Italians do with this Gold Coast pizzeria's take on a spritz, made with prosecco, bitters and orange-flavored Italian liqueur Aperol. It's bubbly, citrusy and infinitely refreshing; if you take a sip and close your eyes, I swear you'll almost feel like you're in Venice. -LA
23. Red sangria at Cafe Iberico
White peach sangria, strawberry sparkling sangria, sweet cherry sangria I do love a variation on a classic, but sometimes nothing but the original will do. This River North tapas bar knows just how to do it by the glass ($6.95), half pitcher ($11.95) or pitcher ($17.95). --LA
24. Dark 'n' stormy at Bar DeVille
The bartenders at this Ukrainian Village bar make a mean version of this classic cocktail made with ginger beer and pucker-worthy lime juice. It gets four stars for the pretty factor thanks to a float of dark rum on top and a big sprig of mint for garnish --JC
25. Champagne at RM Champagne Salon
There are plenty of classy joints around town to sip a flute of champagne, but you can't do much better during the summer than the hidden courtyard patio at this West Loop lounge. There's a bit of bubbly here for just about any price range, from $9 all the way up to $26 per glass, plus tons of options by the bottle. --LA
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