Our 16 Favorite Places To Start Happy Hour Early

UPDATE: This story was originally published on August 10.
The older we get, the more responsible we should become, right? Most of the time, yes. But, while adulthood does bring the burden of bills and extra hours at the office, sometimes letting loose in an unconventional (read: slightly irresponsible) manner is just what the doctor ordered. It's no secret that Chicagoans like to kick back with a few cocktails—so, to help you enjoy this short period of time when the weather is in our favor, we've rounded up our top locales for early-bird sips.
From outdoor patios where you can soak up the last days of the summer sun to indoor retreats where you won't be spotted by your co-workers, our guide to daytime drinking has got you covered. And, don't worry…we won't tell a soul if you leave work. Like, right now.
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Chicago Cut Steakhouse
The best time to appreciate the killer views of the Chicago River and cityscape at Chicago Cut Steakhouse is during the day — especially with a robust glass of vino in hand. As long as the weather is in our favor, the killer patio is the place to be, so don't waste another minute sipping coffee at your desk.
Chicago Cut Steakhouse, 300 North LaSalle Drive (at West Kinzie Street); 312-329-1800.
Drumbar
The newly opened Drumbar is considered Chicago's hottest rooftop speakeasy. You need not know a special password to enjoy specialty libations like the Smoke, a potent blend of Compass Box Peat Monster Scotch, Lapsang Tea, Dumante Pistachio Liqueur, grapefruit juice, and black walnut bitters.
Drumbar, 201 East Delaware Place (at Meis van der Rohe Way); 312-943-5000.
Eno Wine Bar
The Parisians drink wine during the day, so it's perfectly acceptable to snag a seat on the outdoor patio and people watch with a flight — or a bottle — during the daylight hours too. Eno Wine Bar also has a fabulous cheese and chocolate menu, which could quite possibly be the perfect meal.
Eno Wine Bar, 505 North Michigan Avenue (between Grand and Illinois Streets); 312-321-8738.
Estate Ultra Bar
The Miami vibe that Estate Ultra Bar has makes us want to put back cocktails like the Yachtsman (Pernod Absinthe, Bols Genever, Green Chartreuse, Luxardo Maraschino, lemon, simple syrup) all day long. But with the three drink limit this libation has, we better sip slowly...
Estate Ultra Bar, 1177 North Elston Avenue (at West Division Street); 312-582-4777.
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Photos courtesy of Chicago Cut Steakhouse, Drumbar, Eno Wine Bar, and Estate Ultra Bar
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Bread & Wine
This cozy farm-to-table restaurant and bar will make you feel a little less guilty about letting loose during the day. While there's a small outdoor patio, we love enjoying our glass of small-batch wine (the restos specialty) in the homey interior that feels like a friend's awesome pad.
Bread & Wine, 3732 West Irving Park Road (at North Ridgeway Avenue); 773-866-5266.
Market Bar
The name Market Bar really doesn't even begin to describe the variety of spaces where you can while away the hours with a frosty brew. You can choose to play hooky in the indoor dining room and sports bar, outdoor beer garden, rooftop deck, or the sidewalk café.
Market Bar, 1113 West Randolph (between May and Aberdeen streets); 312-929-4787.
South Branch
South Branch is a great daytime drinking destination for those living or working in the Loop. While we are looking forward to its rustic interior come fall, you'll find us on the outdoor patio with a pale ale until they kick us out.
South Branch, 100 South Wacker Drive (between Monroe and Adams streets); 312-546-6177.
Epic
While it may not be the largest in the city, the rooftop patio at Epic certainly isn't lacking in the charm department. Slip into a cabana with a Naked Lady (the drink, that is), a mix of Beefeater Gin, orange bitters, simple syrup, lemon juice and prosecco.
Epic, 112 West Hubbard Street (between Clark and LaSalle streets); 312-222-4940.
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Photos courtesy of Bread & Wine, Market Bar, South Branch, and Epic
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The Chicago Firehouse
The patio at The Chicago Firehouse doesn't get enough cred in our opinion. It's the perfect hidden respite to enjoy a Fireman's Old Fashioned and some crispy calamari before the steak and wine dinner crew rolls in.
The Chicago Firehouse, 1401 South Michigan Avenue (at East 14th Street); 312-786-1401.
Hopleaf
With a name like Hopleaf, we're not going to try and sell you on a wine list. Enjoy your pint along with the mussels that everyone talks about just as much as the beer.
Hopleaf, 5148 North Clark Street (between Foster Avenue and Winona Street); 773-334-9851.
Fulton's On The River
We love the below street level location of the deck (part of Bridge Bar) at Fulton's on the River — just in case we're looking to be a little more incognito about our daytime drinking. Enjoy the afternoon with the Professor and Ginger, a lively combination of Hendrick's Gin, ginger syrup, lime, mint, and ginger ale. Fulton's on the River
Fulton's On The River, 315 North LaSalle Street (between Kinzie Street and Wacker Drive); 312-822-0100.
The Boundary
The Boundary is a Wicker Park watering hole with a large beer list and a huge bar food menu. Sometimes, basic is best — especially if it means getting in before the crazy late-night crowd.
The Boundary, 1932 West Division Street (between Damen and Winchester avenues); 773-278-1919.
Photos courtesy of The Chicago Firehouse, Hopleaf, Fulton's on the River, and The Boundary
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Hubbard Inn
We love the specialty house cocktails (big fans of the Hepburn) at Hubbard Inn almost as much as we adore its antiquey environs. Make friends at one of the communal tables and talk treason over a Hemingway libation (10 Cane Rum, Luxardo, lime juice, grapefruit juice) and some bacon wrapped dates.
Hubbard Inn, 110 West Hubbard Street (between Clark and LaSalle streets); 312-222-1331.
Pops For Champagne
Celebrate the fact that you're having an afternoon beverage with a flute of bubbly at Pops For Champagne. To keep those tiny bubbles from going to your head, order up some gourmet frites made with garlic and truffle butter.
Pops For Champagne, 601 North State Street (between Ontario and Ohio streets); 312-266-7677.
Red Violet
With its sexy red and purple hued interior, an afternoon visit to Red Violet feels as though you're getting a head start on your night out — or you're already there. Belly up to the bar for a Lychee Martini and some dim sum like shrimp shu mai or vegetarian steamed buns.
Red Violet, 121 West Hubbard Street (between Clark and LaSalle streets); 312-828-0222.
Sweetwater Tavern & Grill
Located right on the Mag Mile, Sweetwater offers prime sidewalk seating and an extensive beer and wine list. Even when the weather takes a turn, the interior offers floor-to-ceiling windows overlooking the cityscape and Michigan Avenue, which isn't exactly a bad place to spend an afternoon either.
Sweetwater Tavern & Grill, 225 North Michigan Avenue (between Wacker Place and Lake Street); 312-698-7111.
Photos courtesy of Hubbard Inn, Pops For Champagne, Red Violet, and Sweetwater
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