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The 12 Best Cocktail Bars In Chicago

By Anthony Todd in Food on Oct 21, 2015 4:05PM

Chicago is in the midst of a cocktail boom. Things have radically changed from a decade ago, when a cocktail menu was a novelty and most of the ingredients the bars on this list use hadn’t even been imported yet. These days, it's a bit abnormal if a restaurant or bar doesn’t have a cocktail program.

That doesn’t mean, however, that all drink menus are created equal. There are plenty of bad spots trying to cash in with $20 mediocre martinis, and just because a drink sounds complicated doesn’t mean the mixer knows what they are doing. With that in mind, here are 12 of our favorite spots to kick back and have a well-crafted drink.

A selection of cocktails at GreenRiver. Photo by Kaitlyn McQuaid.

The Whistler

One of the granddaddy’s of the craft cocktail scene, The Whistler is a combination art gallery, concert venue and cocktail lounge. The Logan Square bar turns seven this year, and keeps cranking out some of the most reliable, creative and (importantly) inexpensive drinks in the city. Head in early and grab a seat at the bar and stick around for the music.
2421 N. Milwaukee Ave.

Sea Urchin Mug. Photo by Anjali Pinto, Courtesy of Lettuce Entertain You.

Three Dots and a Dash

This tiki paradise may have lost a tiny bit of its luster when opening bartender (and national star) Paul McGee packed up his shaker and left last year, but its still one of the prettiest bars in town, even if the menu has gotten slightly less classy. New bar manager Diane Corcoran is serving up creative twists on tiki classics like the Poipu Beach Boogie Board, a combination of rye, rum and fruits that will have you feeling like you’re on a boogie board of your own after two or three.
435 N. Clark St.

The Drifter

This relative newcomer to the scene opened early in the year, and has already established itself as a must-visit. Hidden underneath the venerable Green Door Tavern, this spot fancies itself as a modern day burlesque hangout, with drinks printed on tarot cards and quirky acts evoking a circus sideshow playing in the background. Get there early or be prepared to wait, because the place is tiny.
676 N. Orleans St.

The interior of The Drifter. Photo via Facebook.

Sable Kitchen and Bar

There aren’t many restaurant bars on this list - often, the bar gets lost in the concept, and you don’t always want to drink three rounds of complicated cocktails while trying to eat your dinner. Plus, aren’t downtown hotel bars usually bad? Well, Sable has been bending the rules since it opened, turning out complex drinks to a huge restaurant without breaking a sweat. New bar manager John Stanton has already put his stamp on the menu, and Sable promises to be a destination for years to come.
505 N. State St.

Punch House

One of the best things about Chicago’s cocktail scene is that it’s not just centered in downtown and River North. Many of the best bars are out in the neighborhoods, and Punch House is a perfect example. Located in Pilsen underneath Dusek’s, Punch House uses antique methods to make delicious punches, and serves them in a space with a '60s rec room vibe, complete with fish tank. If there’s a milk punch on the menu (and there usually is) get it—the sweet, creamy drink with a cognac base is a great way to end your night.
1227 W. 18th St.

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The Coal Miner's Daughter at GreenRiver. Photo by Kaitlyn McQuaid.


The newest newcomer on this list, GreenRiver has the most extensive, complicated and exciting cocktail list to come to the city in months. From the same team behind New York’s Dead Rabbit, GreenRiver’s list is themed around Chicago history, with extensive blurbs on Irish-American historical figures and how they inspired the drinks named for them. This place pulls no punches, with ingredients like mushrooms, soy, coffee, and other things I haven’t even heard of before, but they all come together to make some of the most interesting (and sometimes pricy) drinks around.

259 E. Erie St.

Drinks at The Berkshire Room. Photo via Facebook.

Berkshire Room

The Berkshire Room, helmed by bartender Ben Schiller, still has my single favorite drink in town - the Weston, made with whiskey, coffee and pipe tobacco essence. But that’s not the only thing to love at this gorgeous bar, located in a marble-filled converted hotel lobby. They’ve got a creative cocktail menu, a list of cheap beers, and an antique spirits list complete with whiskeys that are literally impossible to get anywhere else. It can get a little loud and broish on the weekends, but during the week it’s a great quiet hangout.
15 E. Ohio St.

The Aviary

O.K., so it’s a bit pretentious, and the drinks are crazy expensive. But I’ve become much more of a fan of this bar from the folks behind Alinea and Next since they implemented the Tock ticketing system that allows you to get a reservation in advance. Grab a seat and hang on, because these drinks can get a little crazy. If you can manage to worm your way into the much-more-comfortable secret bar, The Office, underneath, go for it—and don’t worry that your credit card will come out kind of sad, it’s a memorable experience.
955 W. Fulton Market

The new syrup, photo courtesy of The Violet Hour

The Violet Hour

It’s the original fancy Chicago cocktail bar, and it’s still keeping up with the times. Sidle up to the unmarked door in Wicker Park and walk into the perfect dark, candlelit romantic drinking space - especially if you’re into bars where you can talk to your companion and enjoy your beverage without televisions or other patrons blaring in your ears. The seasonally-rotating drink menu rarely has a miss, and if you don’t like the options, the bartenders will craft you anything you want. Not a fan of drinks with 98 obscure ingredients? This is a good spot for you, because simple and balanced is their signature style.
1520 N. Damen Ave.

Lost Lake

When he left Three Dots, Paul McGee didn’t disappear - he just moved across town. While comparisons to the other big tiki bar in town are inevitable, Lost Lake is a total different animal - a chill neighborhood joint with a thatched roof and drinks that will blow you out of the water. My favorite feature is the rotating nightly daiquiri, an inexpensive way to try new and exciting rum selections. Follow it up with a “Saturn in the House of Saturday Forever,” combining rum, gin, fruit, falernum and Letherbee Besk (their version of Chicago classic Malort).
3154 W. Diversey Ave.

Barrelhouse Flat

If you’re looking for an encyclopedic drinking experience, rather than a preciously-curated one, head to this Lakeview bar with a cocktail menu that spans pages and pages. They’ve got any drink you can imagine, and they’re all perfectly crafted. The main bar is pretty, but if you can get upstairs to the wood-and-red-velvet-covered paradise and sit in front of the fireplace you’re guaranteed to have a great night.
2624 N. Lincoln Ave.

Billy Sunday

Yet another great Logan Square bar, Billy Sunday channels the feeling of an antique Chicago tavern better than any other cocktail spot in the city. You can practically feel the warmth of gaslights walking into this bar. My favorite part of the menu is the “good book,” a giant leatherbound volume of antique bitter amaros and scotches that is totally unique in the entire cocktail world. They’ll pull down a faded bottle from the 1950s and pour out the final drop - it’s like tasting another world for the last time.
3143 W. Logan Blvd.