Dan Smith

Navy Strength Old-Fashioned

at Queen Mary Tavern

In this era of fancy techniques and infusions, wild garnishes and unorthodox flavors, it’s the very simplicity of this drink that makes it stand out. It sets a new standard for old-fashioneds, starting with the fact that it doesn’t use whiskey. Dan Smith, beverage director of this maritime-inspired tavern, tapped high-proof versions of rum and gin and mellowed them out with Demerara syrup, angostura bitters, and a little salt. It’s perfect. $14. 2125 W. Division St., Ukrainian Village

1 oz. Smith & Cross rum 1 oz. Hayman’s Royal Dock gin
⅛ oz. Demerara syrup (2:1 sugar to water) 2 heavy dashes angostura bitters
1 tiny pinch salt Orange peel, to garnish

1. Combine all ingredients in a mixing glass with ice and stir briefly.
2. Pour into a double rocks glass with a single large cube. Garnish with an orange peel.

Videography by Edgar Ramos

No. 2

Trader Vic Mai Tai

at Three Dots and a Dash

There’s been a mai tai on the menu since Three Dots opened in 2013, but this latest version is most in line with the one that cocktail legend Trader Vic Bergeron created in 1944. Beverage director Kevin Beary uses aged Barbados, aged Fijian, and overproof Jamaican rums to mimic the now-defunct rum in that very first mai tai, then tweaks it until he finds the perfect balance of orange curaçao, lime, and orgeat. Historic yet forward thinking, this drink hits just right. $20. 435 N. Clark St., River North

Photograph: Powell Jordano

Amaro Daiquiri

at Billy Sunday

No bar in town has a better handle on Italian bitter liqueurs. Its twist on the classic daiquiri features herby Amaro Noveis and rhubarb amaro shaken with lime and sirop de capillaire (a syrup of maidenhair fern and orange flower water). The balanced sip lands, improbably, right at the intersection of bitter and refreshing. $15. 3143 W. Logan Blvd., Logan Square

No. 4

Negroni Slushy

at Parson’s Chicken & Fish

On the menu since the first location opened in 2013, the slushy that started the slushy trend is made with local Letherbee gin and Misoo bitter aperitivo along with sweet vermouth and citrus. Slurping one down on the sprawling patio on the first hot day of the year is a Chicago bucket-list experience. $13. 5721 N. Clark St., Andersonville; 2435 N. Halsted St., Lincoln Park; 2952 W. Armitage Ave., Logan Square

No. 5

Ume Boulevardier

at Kumiko

Julia Momosé’s drinks shine a light on Japanese spirits, as is the case with this lovely take on the classic Boulevardier. Created for the bar’s opening in 2018, it combines Japanese whisky, Campari, and Cocchi Americano Rosa with umeshu, a plum liqueur, for punchy sweetness. $20. 630 W. Lake St., West Loop

½ oz. Mito no Kairakuen 5-year umeshu ½ oz. Campari
1 oz. Cocchi Americano Rosa 1 oz. Iwai 45 whisky
Lemon peel, to express Orange peel, to garnish

1. Combine all ingredients in a mixing glass with ice and stir.
2. Pour into a rocks glass with ice cubes. Express a lemon peel over the top, then garnish with an orange peel.

Photograph: The Alinea Group

Jungle Bird

at the Aviary

In what could double as a science project on liquid density, this twist on the tropical drink features two layers of rum, a layer of Campari (with gushy spheres of rum suspended within), and a base of tangy and sweet pineapple-lime simple syrup. It adds up to deliciousness. (Use the wide straw to suck up all the flavors.) $30. 955 W. Fulton Market, West Loop


at Moneygun

The ’90s may be back, but we don’t necessarily want to drink like it. And at Moneygun, the Cosmo has been deftly updated. The bartenders infuse Triple Sec with dried hibiscus flowers and make a cranberry-lemon cordial to amp up the tartness. (We’ll keep the soundtrack of ’90s jams, though.) $13.50. 660 W. Lake St., West Loop

Sportsman Cocktail

at Sportsman’s Club

While the rest of the cocktail list at this neighborhood spot changes daily, this boozy sipper is a constant. The glass is rinsed with absinthe, then filled with a bittersweet blend of bourbon, Zucca Rabarbaro, Luxardo Bitter, and angostura. Both the drink and the bar are Chicago classics. $13. 948 N. Western Ave., Humboldt Park

No. 9

Space Cowboy

at Nine Bar

Joe Briglio and Lily Wang do many things well at their sleek Chinatown bar, but they have a particular knack for highballs. Their latest is made with Japanese whisky, local Rhine Hall apple brandy, Cynar, and blackberry liqueur. It’s brightened up with ginger and lemon juices and topped off with Topo Chico. The only issue is how fast it goes down. $13. 216 W. Cermak Rd., Chinatown

1½ oz. Kikori whisky ½ oz. blackberry liqueur (Nine Bar uses Fruitful Mixology brand)
1/4 oz. Rhine Hall apple brandy 1/4 oz. Cynar
1/4 oz. ginger juice 1/4 oz. lemon juice
Topo Chico, to top Lemon wheel, to garnish

1. Combine all ingredients in a Collins glass with ice cubes and stir.
2. Fill the rest of the glass with Topo Chico and garnish with a lemon wheel.

No. 10

Bowl of Fire

at Sepia

Keith Meicher has fun with the cocktail program at this Michelin-starred restaurant. Take this drink: He stirs together El Tesoro reposado tequila that’s been aged in former Knob Creek whiskey barrels, Bénédictine, and cherry bark bitters, then pours it into a vessel with smoke from barrel staves. A play on a Martinez, this cocktail is as elegant as its surroundings. $28. 123 N. Jefferson St., West Loop

Photography: Rose Mary
No. 11

Rum Coconut Milk Punch

at Rose Mary

Kyle Davidson, who headed up the beverage programs at Blackbird and Elske, quietly took over the bar here in 2022. Where he goes, serious drinkers need to follow. His menu is jammed with hits, but this one, a perfectly clear, stirred colada accented with quince and oolong, is the must-order. $16. 932 W. Fulton Market. West Loop

No. 12


at Estereo

This fizzy cocktail reflects the easygoing vibe of this all-day Latin spirits bar. It’s made with yerba maté, Falernum, lime, and the spirit of your choice. There’s no wrong answer here, since the nutty, herby flavors work with anything, but the rhum agricole adds a nice grassy funk. $12. 2450 N. Milwaukee Ave., Logan Square; 1001 W. Fulton Market, West Loop

Photograph: Rob Brenner

Forest Fire

at the Whistler

You don’t encounter too many shaken Scotch cocktails, which is a shame, because this one from owner Billy Helmkamp demonstrates how great they can be. Inspired by the woodsy walks he took on a trip to Finland, it features spruce-tip-infused Scotch, orgeat, lime, and barrel-aged bitters. It straddles the line between wintery and tropical, which makes it the ideal balm for cold Chicago evenings. $14. 2421 N. Milwaukee Ave., Logan Square

1 oz. Compass Box Glasgow Blend Scotch ½ oz. spruce-tip-infused Laphroaig 10-year single-malt Scotch
1 oz. Liquid Alchemist orgeat 3/4 oz. lime juice
6 drops Fee Brothers whiskey-barrel-aged bitters

1. Make the spruce-tip-infused Laphroaig: Combine 1 liter Laphroaig with 2 ounces spruce tips (available at spruceontap.com) and let sit for a week. Pour through a coffee-filter-lined strainer into a bottle.
2. Combine all ingredients in a cocktail shaker with ice and shake. Strain into a Nick and Nora glass.

Photography: Best Intentions

Todd Appel’s Year-Round Horchata Margarita

at Best Intentions

Todd Appel, a bartender who sells syrups and cordials through Appel’s Cordials, initially created this drink for outdoor imbibing. It’s made with his cinnamon-spiced oat orgeat, tequila, lime, and a dash of angostura. The warming spices and creamy texture give it a complexity apt for any season, but it remains an easy patio crusher. $10. 3281 W. Armitage Ave., Logan Square

Monica Casillas-Rios
No. 15


at Elske

Martinis are so personal — some like them dry, others wet; some with gin, others with vodka. But no one can argue about this riff from Monica Casillas-Rios, who nabbed a Michelin award last year. She infuses vermouth with dill and cucumber, then stirs it with vodka and Salers, an herbal liqueur, for a drink that straddles the line between a 50-50 martini and a white Negroni. $15. 1350 W. Randolph St., West Loop

Photography: Kelly Sandos

The Violet Touch

at the Violet Hour

It’s a good sign when the bartender serving you says, “This is the drink we all get when we come in ourselves.” It’s easy to see why: With rye, smoky rhubarb amaro, rich PX sherry, and tobacco bitters, this is a grown-up cocktail for when you just want to take a step back from it all. $17. 1520 N. Damen Ave., Wicker Park

Photograph: Shon Gibbs
No. 17

Double Chai Daiquiri

at Lilac Tiger

This spiced number from David Mor is a perfect companion to Zubair Mohajir’s Southeast Asian fare. Mor infuses rum with chai, then shakes it with Indian single-malt whisky, lime, and a chai syrup made with black tea, green and black cardamom, jaggery, ginger, black pepper, and cinnamon. “It’s my favorite cocktail on the menu,” he says. Ours too. $15. 1742 W. Division St., Wicker Park

El Sótano

at Bar Sótano

This shaken refresher, the namesake drink at Rick Bayless’s cocktail spot under Frontera Grill, is made with mezcal and sugarcane and lime juices, plus hoja santa syrup and green Chartreuse for an herbal punch. Light and easy, it’s the right thing to kick off the night — especially along with an order of the pork carnitas taquitos. $16. 443 N. Clark St., River North

1½ oz. Cuentacuentos El Barro mezcal 1½ oz. sugarcane juice (like Goya brand)
¾ oz. lime juice ½ oz. hoja santa syrup
½ oz. green Chartreuse

1. Make the hoja santa syrup: In a pot, dissolve 1 liter cane sugar in 1 liter water, then bring to a boil. Add 65 grams dried hoja santa, then remove the pot from the heat and let steep overnight. Strain into a bottle and store in the refrigerator for up to 2 weeks.
2. Combine all ingredients in a cocktail shaker with ice and shake. Double-strain into a coupe glass and garnish with a dehydrated lime.

No. 19

Red Snapper

at Scofflaw

If you prefer to treat a Bloody Mary as a drink rather than a whole appetizer, seek out Danny Shapiro’s refined gin-based version. Available for brunch, it’s gently spicy with a mix of lemon, mustard, Worcestershire, and celery salt. $13. 3201 W. Armitage Ave., Logan Square

Frozen White Russian

at Avondale Bowl

There are White Russians at bowling alleys, and then there’s this White Russian at a bowling alley. The revelatory slushy is made with vodka, local Maplewood coffee liqueur, coconut cream, and oat milk. It’s vegan, it’s half-price on Thursdays, and it’s a reminder that, above all, cocktails are supposed to be fun. $12. 3118 N. Milwaukee Ave., Avondale