Cheers! 7 New Chicago Watering Holes

Time for a booze cruise! Okay, fine: not a real booze cruise, since Lake Michigan's so frozen it may never thaw again. But, cruising between these new Chicago watering holes is sure to warm you up. And, drinking craft cocktails and cask beers is way better than being captive on a boat with overpriced well drinks anyway.
From a grandpa-esque basement with a giant aquarium behind the bar to the distillery serving perfect (and extra-strong) martinis to the Wicker Park tap room with 36 craft beers (and Fernet Branca!) on draft, these spots are worth ducking out of work early. Just don't blame us if you come home a little tipsy…
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Photo: Courtesy of CH Distillery.
CH Distillery
We're all for cocktails with infusions and house-made syrups and fancy bitters, but the reason we tell everyone to come to this new bar/distillery hybrid on Randolph Street is for something much simpler: a straight-up gin and tonic. You won’t find a better one in the city, which really is how it should be when you're the only bar in the city where the gin is made on site. If you're more of a vodka, rum, or whiskey person, good news: CH distills that, too. Start with the most basic cocktail you can find and savor the liquor-forward flavor. After that, venture into the fancier stuff, like the Czech Mate (spice-infused vodka, grapefruit juice, and honey syrup) — it's delicious, too. A delight for total spirits geeks: The narrow dining room has massive windows overlooking CH's custom-built stills.

CH Distillery, 564 West Randolph Street (at Jefferson Street); 312-707-8780.
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Photo: Courtesy of Lone Wolf.
Lone Wolf
This new Randolph Street spot is everything you want a bar to be: dark, comfortable, completely unpretentious, home to a drink list from Barrelhouse Flat’s Stephen Cole, and boasts a menu of savory pies from Pleasant House Bakery in Bridgeport. Get cozy in a high-backed booth and order the Seven Sisters, a pleasantly bitter cocktail with Fernet Branca and two types of amaro, or one of three sgroppinos, fruit-forward cocktails inspired by Italian after-dinner drinks.

Lone Wolf, 806 West Randolph Street (at Halsted Street); 312-600-9391.
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Photo: Courtesy of Big Bar.
Big Bar
After a recent remodel, this shiny drinking destination in the Hyatt on Wacker Drive professes to have the longest bar on the continent, a fact we would happily verify by visiting every bar on the continent if Hyatt would pay for it. We kid (sort of). In any case, it’s a really big bar, complete with a really big 1,400-bottle liquor collection and really big 90-inch televisions and a really big view of the Chicago River and the Wrigley clock tower, which is all perfect if you’re gathering a large group — particularly a work happy hour, given the hotel’s proximity to the Loop. And, we can’t forget the big drinks, although if you have too many, you undoubtedly will; options like the mangotini or the spiced ginger-pear martini are available in whopping 48-ounce glasses.

Big Bar, 151 East Wacker Drive (at Stetson Avenue); 312-565-1234.
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Photo: Courtesy of The Dawson.
The Dawson
On paper, this new River West spot is as much a restaurant as it is a bar; in practice, the drinks are the real reason to go. And, there's a very compelling reason: The cocktail menu is from Annemarie Sagoi, who we've had a crush on since her days inventing sophisticated Jell-O shots (surprisingly not an oxymoron) at the Charleston. Similar jigglers are available here as an off-menu treat, or order from a list of about a dozen cocktails. Many have a pleasant sweet component, from pineapple syrup to cherry phosphate. If you're looking for something boozier, we love the Officer's Club, with two types of Scotch, aperol, Thai bitters, and lemongrass.

The Dawson, 730 West Grand Avenue (at Halsted Street); 312-243-8955.
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Photo: Courtesy of Punch House.
Punch House
Between the wood paneling, tiled floor, tufted leather bar stools, ’70s low-slung couch, and shelves of knickknacks, this bar beneath Dusek’s in Pilsen is strangely reminiscent of our grandpa’s basement when we were growing up — which is, by the way, a major compliment. The two big differences: That was B.H. (before hipsters), whereas Punch House is home to every tuft of ironic facial hair in Pilsen. And, Gramps didn’t have boozy punches on tap for us (probably for the best when we were 8). Try the Philadelphia Fish House, in which peach liqueur adds just the right hint of sweetness to rum, cognac, and lemon.

Punch House, 1227 West 18th Street (at Allport Street); 312-526-3851.
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Photo: Courtesy of Analogue.
Logan Square's newest cocktail bar may come from two Violet Hour vets, but don't expect Analogue to be anything like the dark, hush-hush speakeasy with a hefty booklet of drink options. What you can expect: a small space offering six cocktails, a shot of the day, some solid craft beers, and $3 Budweisers. Plus, DJs spinning soul music and a makeshift dance floor at whatever hour it feels appropriate to push all the tables to the side. To clarify, the shot of the day isn't going to be an O-bomb (think shots based on classic cocktails) and the cocktails are, as expected from VH alumni, high-end (with ingredients like smoked brown sugar and pumpkin bitters). But, ultimately, this is a relaxed bar where anything goes. Just get there early — the small space fills up fast. P.S. At only $10 each, these cocktails are the biggest steal since The Whistler.

Analogue, 2523 North Milwaukee Avenue (between Logan Boulevard and Sacramento Avenue); 773-904-8567.
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Photo: Courtesy of Links TapRoom.
Links TapRoom
The numbers are in, and they’re impressive: 36 craft beers on tap, 40 by the large-format bottle, 10 by the can, and four served straight from the cask. Welcome to Links, a chill new Wicker Park beer bar where you can drink, chow down on sausages with giardiniera, and fries with bacon apple butter — and then drink some more. Links is also tapping into (see what we did there?) some pretty cool technology. Digital screens above the bar show how much beer is remaining in each keg so you know if you should knock down the guy next to you to get the last pint of Dark Horse.

Links TapRoom, 1559 North Milwaukee Avenue (at North Avenue); 773-360-7692.

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