Because drinks with awesome views of Chicago > drinks without awesome views of Chicago, here are 17 places to enjoy the former, from rooftop bars in the heart of the city, to pond-side tipple-ries with Michelin stars.
The Loop Armed with expansive, western-facing views of the city from its iconic location atop the 40th floor of the Chicago Stock Exchange, Everest offers more than just a dining experience by famed Chef Joho. It also offers booze. Really, really good booze. And lots and lots of it. We're talking 1,600 bottles of wine and, according to The New York Times, "The Country's Best Selection of Alsace Wine." Pro tip: the truffle risotto is a must.
This Vintage Cocktail Lounge Is in a Rare Airplane From the 1960s
River North This super-elegant spot inside The Langham has one of the absolute best views right in the heart of Chicago -- courtesy of those floor-to-ceiling windows -- and has enough curated cocktails (and seriously addicting fried pinwheel pasta bar snacks) to make enjoying them for a whole bunch of hours totally doable. Oh, and there's also a live harpist, a killer Mediterranean menu, and chicken wings that are on fire (literally!). So. There's. That. Cocktails to try: Trinidad James, London Dove, and Beet It.
River North Day or night, Dana Hotel's rooftop lounge/club/restaurant brings the mile-high, middle-of-the-city-view goods, and along with them strong house cocktails and a chance to let your inner voyeur flag fly -- the indoor-outdoor rooftop gives you a bird's eye view into all the surrounding high-rises.
River North The view from this newly remodeled roof (there's so much more room for activities!) will make you feel honored to be living in Chicago, as it plants you right in the midst of River North. The cocktails from this newly remodeled roof will make you feel not much of anything. Enjoy.
Lincoln Park Located inside Lincoln Park (the actual park), this Michelin-starred restaurant is not only one of Chicago’s oldest restaurants, but it’s also the only one located next to a real, live pond. Also cool: a buck from every bottle of wine you purchase (pro tip: purchase a bottle of wine) gets donated to any of four local charities that push the sustainability envelope.
Gold Coast Because sometimes you get tired of Chicago's architecturally acclaimed skyline* (*lie), hit up Spiaggia, which throws down gorgeous views of Lake Michigan and Oak St, which you can take in while downing classic cocktails, Italian beers, and expressive wines.
River North The Langham's cool little sidewalk cafe occupies prime real estate on the riverside plaza, which means stunning river panoramas, plus the opportunity to drink any of four six-person punches in prime riverside plaza real estate. Awesome extra: each table comes equipped with its own boombox and pre-set playlist.
River North Another special occasion spot with out-of-this-world unobstructed views, the Terrace at Trump is pretty spectacular when it comes to looking points of Chicago. The unrestrained views of the river, lake, and city peer through the skyscrapers and over the bridges, creating an awe-inspiring feeling of depth in a city oasis. Note: you’re paying for the view and the venue, not the drinks, so opt for wine over cocktails. Also, having a Lobster Maitake Roll and the K-Chick Steam Bun can't hurt.
Gold Coast This upscale whiskey bar focuses on expertly crafted cocktails, with an intimate and cool cocktail patio atop Raffaello Hotel. The 18-cocktail menu showcases house-made infused syrups and a concentration on savory drinks. Try the My Little Lotus, Figgin’ Awesome, and Generally Mackin’ (triple fisting!).
Streeterville You’re 95 floors up. You can see everything. Probably even Michigan and Indiana on a clear day. It doesn’t matter what you order (though a martini seems appropriate). And just beg to be seated near a window.
Loop If you’ve ever walked across the bridge from the Modern Wing at The Art Institute of Chicago and wondered why you can’t just sit and take in that view of Chicago’s massive skyline, now you can. Terzo Piano is one of the best (liquid!) lunch spots for dropping your jaw over Chicago’s Mag Mile view. Bloody Marys and Negronis? Both things you should be drinking here. FYI: Terzo Piano only does dinner on Thursdays and brunch on Sundays, but it's open for lunch daily.
Loop Since we all know how temperamental Chicago’s weather can be, it's nice that Tavern at the Park has indoor views from a glass atrium that's called “Tree House.” Views of South Michigan Ave and Millennium Park pair with the "Stop! Tequila Thyme!" (which features a vanilla bean, thyme & cucumber-infused Maestro Dobel tequila served in a heated snifter over a rocks glass of boiling water!).
Lincoln Park This gem of a rooftop at Hotel Lincoln sports a view built to extend your day drinking time (as will the 10 craft cans) -- a serene lake look that also provides a nice escape from the cookie-cutter Downtown rooftop scene.
River West Surpass the loud dining hall (sorry Morimoto) and head downstairs to The Blue Room, which offers a unique view of Chicago -- the river is literally level with you, and on the other side of it? The more industrial side of Chicago. Skip the food, but do try the Morimotini, and ask for sake recommendations.
River North All shiny and new, Rockit’s relaunch is so versatile you could stop here on the way to a gala or game and not be out of place. With garage door entrances and a revamp of the interior and exterior, the cool new upstairs lounge has windows that open onto the street with massive views of Hubbard St nightlife. Try the pork belly nuggets with a Rockit Old Fashioned or The Kipling (upstairs menu).
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Danya is contributing writer for Thrillist, who moved to Chicago to dabble in graphic design, fashion, and journalism. In short, to basically take the city by storm. Follow her at @directedbydanya.