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Best Outdoor Drinking Spots in Chicago

Photo for: Best Outdoor Drinking  Spots in Chicago

08/10/2020 From the surrounding decks with stunning views over the skyline to the strident beer gardens to the cozy patios, here are the best outdoor drinking spots in Chicago.

(Header image credit: LH on 22 at London House Chicago)

Chicagoans have plenty of options to participate in two of their favorite summer pastimes from the surrounding decks with stunning views over the skyline to the strident beer gardens to the cozy patios concealed behind the neighborhood's taverns.

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We have just the place for you, whether we want to impress a date or meet friends after work.

Ten Cat

Ten Cat had been an under-the-radar entry on our list of the best fireplace bars, and its patio also makes the cut a low-key spot to drink with friends. It's the next best thing to have a backyard of your own.


Montrose Saloon

The patio of the saloon has some of the same facilities as its trendiest counterparts — the bocce courts, the communal tables (right from Germany) and the hop vines scaling the "Green Monster" wall — but the corner bar is still in its heart.

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Half Acre

It's the first summer of the Bowmanville taproom and beer garden Half Acre, which opened in autumn 2017. Opt for more than one visit to work your way through the list of Half Acre tap brews and get hungry, too. Eats are a step above the pub grub, like herb-roasted salmon and duck liver pate. Keep an eye out for updates on the annual Big North Bash, where the whole brewery is run by the visitors.

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LH on 22 at London House Chicago

Folks stared up at London House forever — one of the "big four" skyscrapers soaring over Michigan Avenue and the Chicago River. Now check out the opposite view from the LH rooftop bar on the 22nd floor of the building. Spoiler Alert: It's unbelievable.

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Apogee Lounge at Dana Hotel

The breathtaking view from Apogee's 26th-floor bar is hard to beat, but the cocktails here offer the skyline a run for its money. Created by Ben Schiller, an exceptional mixologist, the cocktail menu is Instagram gold: beautiful colors, ingenious use of flowers and ice cream, and custom barware. Reservations are strongly recommended.

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Aire at Hyatt Centric The Loop

Hamm's Expense at Aire: 8 bucks. That feeling of being above all else: priceless. If you meet friends here for drinks after work, be specific: this 24th-floor rooftop bar mixes up a name with Aire Ancient Baths, which is a totally different kind of hangout.

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The Bistro at Streeterville Social, Loews Chicago Hotel

See the sunset from this oasis in the sky as you drink a cocktail that tastes like a summer bottle. Stop by for # WeDrinkPink Wednesdays, when the rosé glasses are just $5.

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Tree House at Tavern at the Park

Tavern at the Park has a good enough sidewalk cafe, but for a next-level experience, head to the Tree House rooftop lounge with a view of Millennium Park. The Tree House opens for the season of May 25, no reservations approved, closed on Sundays.


Cabana Club at The Robey

A day at the Cabana Club is a must for a vacationer. Order mojitos from your deck chair, dip your legs in a tiny pool (the staff says it suits 15 people with a drinking room) and take a photo of yourself floating across the Caribbean instead of lounging six floors above Wicker Park. To enhance the illusion, carry earbuds to block the rumble of the Blue Line trains going by.

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Whiskey Business

The name here says it all, but it's not exactly. Yeah, there's a big list of whiskeys, but there's also a way to make less sophisticated choices, including boozy popsicles, "adult" Capri Sun, and frosé. TV screens make the rooftop a perfect spot to watch Cubs or Bears al fresco. The signature menu item also sounds straight out of Wrigley — hand-cut fries with plenty of seasoning options ranging from Blazing Hot Cheetos to chocolate. Whiskey Company sometimes holds karaoke and yoga brunch parties on its rooftop.

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Big Star

Big Star's recipe is very simple: alcohol + tacos = fun. When the Margaritas and Micheladas are flowing, there's no doubt that the Big Star has a good thing going on. Will the same magic formula work at Wrigleyville's new Big Star location? Umm, well.

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Kaiser Tiger

Whenever it comes to beer gardens, bocce is a new bag (though nothing in our hearts can dethrone Jarts). Kaiser Tiger has courts that are used for curling in the winter. But don't make a mistake — and how could you, it's written on the building—"sausage, bacon and beer "are the real attractions here.

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