Where To Get a Sidecar Cocktail In Chicago

Order a Sidecar from one of these places.
Where To Get a Sidecar Cocktail In Chicago image

photo credit: Sandy Noto (taken before shutdown)

If we asked you for a Sidecar, you might draw us a picture of a vintage motorcycle. Cool as that might be, it’s not what we were looking for. Instead, we’d hope you’d hand us a Sidecar cocktail. Or if you don’t happen to have Cognac, orange liqueur, and lemon juice handy, you’d go pick up an excellent version at any of the spots on this guide.

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The Spots

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Bar Food

River North

$$$$Perfect For:Casual Weeknight DinnerDining SoloDrinking Good CocktailsDrinks & A Light BiteEating At The BarFirst/Early in the Game Dates
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Good Measure makes fantastic drinks, and this River North bar recently opened a large patio. And while it’s a great spot to hang out, cocktails are also available to-go. Also worth noting - this place is a great restaurant, too, with dishes like Nashville hot-fried duck livers, warm pimento cheese, and an excellent burger.

This West Loop spot is a barbershop in the daytime, but at night, Blind Barber turns into a bar. And this year, this bar/barbershop hybrid has an outdoor patio so you (and your great haircut) can drink outside.



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The large sidewalk patio at Proxi is perfect for enjoying small plates (like tempura elotes or burrata), drinking cocktails (like a sidecar), and ordering more small plates and cocktails.

Neon Wilderness is a bar in Wicker Park near the Division Blue Line stop. It serves fun cocktails (including one made with Malort, and, of course, a sidecar), and affordable cans of beer. They also have a spacious back patio.



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Lazy Bird specializes in cocktails that are updates on classics (like the Clover Club or a daiquiri made with aguardiente) and we haven’t had a bad one yet. And yes, this includes the sidecar.

This Italian restaurant in Bucktown is meant to resemble a 1940s supper club, and that’s why coming here always puts us in the mood for a classic cocktail. And while they’re famous for their signature martini, they also make a fantastic sidecar.

During the summer, you should make Saint Lou’s Assembly a part of your regular rotation. This spot has a great outdoor space, where you’ll find a covered area with picnic benches, round tables on mulch, stadium seating benches, and an outdoor bar so you never have to go inside.

Sportsman Club opened in 2013, but has an old school feel (with a big wooden bar and leather seats), and a focus on classic cocktails. But this tavern also has a fantastic hidden back patio with lots of space between tables.

This River North spot has a lot going for it right now. This summer they debuted a brand new sidewalk patio, and now they also have a great Happy Hour - Wednesday through Friday all cocktails are half-off from 4-6pm.

Willow Room in Lincoln Park is an upscale restaurant that makes a great classic Sidecar - Rémy Martin, orange liqueur, and an orange peel. It’s straightforward and delicious.

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