OMl Worldwide

5 Spots to Get the Best Cocktails in Chicago

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This blog was originally published in 2015; we have since updated it to reflect the best and more accurate information possible. 

So you’re planning a night out in Chicago, and you’re looking for the best cocktails the city has to offer.

Maybe you’re new to the world of specialty beverages; maybe you’ve enjoyed the best drinks in a variety of great spots in different cities.

Whatever is your level of sophistication, we’re positive Chicago has a drink to impress your palate.

Whether you’re planning a night out with clients, planning for a special date with your sweetheart, or simply looking for a way to unwind after work, these five cocktail stops should be on your Chicago radar.

1. The Barrelhouse Flat

2624 North Lincoln Avenue, Chicago

About the Bar: This environment is built for the cocktail-passionate.

The bartenders and servers know their stuff, and you have a ton of menu items to choose from. Appetizers like gourmet popcorn and lobster mac and cheese, as well as main dishes like sliders and poutine populate the menu.

About the Drinks: Their drink menu is sophisticated, and might require a question or two to the bartender about what’s what and what’s good.

The cocktail menu is divided into “Shaken” and “Stirred” options, and each subsequent page of the menu specializes in a particular spirit. The Lion’s Tale, for instance, with bonded bourbon, lime, simple syrup, pimento dram and bitters, is perfect for those who appreciate the complex flavors offered by a whiskey cocktail.

2. The Grafton

4530 North Lincoln Avenue, Chicago

About the Bar: A traditional Irish Pub and Grill, the Grafton’s menu features traditional Irish comfort foods like lamb stew and beer-battered onion rings. The environment is decidedly Irish pub, with heavy wooded fixtures and dark leather booths, a great outdoor seating area and an impressive selection of beers. .

About the Cocktails: The Grafton’s winter cocktail list features entries like the Sippin’ Gin Fizz, coming in way under Chicago’s average cocktail price, at only $8. You can also get a Negroni, with dry gin and sweet vermouth, or a delectable Irish coffee with Jameson whiskey, again a steal at only $7.

3. Celeste

111 West Hubbard Street, Chicago

About the Bar: The menu has eats like lamb shoulder and crab, fit for the upscale vibe of the décor and the majority of the clientele. They also have octopus for the more adventurous palate. There is both a raucous downstairs area and a more tranquil upstairs area. If you go during the summertime, you can enjoy Celeste’s rooftop lounge area, as well.

About the Drinks: An impressive selection of $10 cocktails, with options available like the strawberry sour with gin and the Golden Filigree.

4. The Revel Room

1566 North Milwaukee Avenue, Chicago

About the Bar: Think lots of heavy leather furniture and wood finishes and a dark and ambient atmosphere perfect for unwinding after work or enjoying some time with friends. They have a variety of affordable beers, both canned and on draft, as well as a selection of wines.

About the Drinks: They have a small but impressive selection of $10 cocktails, like the Golden Bullets and Vampires which features Terrior gin, apricot cordial, lime and cinnamon cider. The Sky Hook features blended Scotch, coffee heering, amaro, honey and cream.

5. The Berkshire Room

15 East Ohio Street, Chicago

About the Bar: Though it’s nestled into the bottom of Chicago’s ACME Hotel, the Berkshire Room attracts its own devoted crowd each night. Their appetizer menu features affordable bar snacks like pickled vegetables, onion dip and popcorn, while their entree list features items like ham and pimento cheese, BLT sliders, and pheasant pot pie.

About the Drinks: House cocktails are $12 a pop, but pack a punch; the Swipe Right features tequila, yellow chartreuse and smoked salt, while the Kung Fu Grip features rum, grapefruit and lemon.

The items on their Barrel Finished Cocktails list are $15, and features listings like Old Money, with bourbon, aperol, walnut liqueur, and allspice. For $14, you can request a “Dealer’s Choice” cocktail; simply provide your server with your chosen spirit, flavor profile and glassware and the Berkshire’s expert bartenders will make you a specialty drink.

These, of course, aren’t the only amazing cocktail stops in Chicago; they’re just a few of our personal favorites.

OML Worldwide Transportation would like to remind you to drink responsibly, and always have a safe, sober driver available to handle your transportation after a night of cocktails and fun.

Top Photo Credit: Kevin Dooley

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Dale Schahczinski
Goal driven team leader, with industry experience spanning all aspects of operations and administration.