Chicago’s Top Rooftops and Patios

Chicago's coolest outdoor spaces for a drink and a bite.

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With summer just around the corner it's time to enjoy the great outdoors and grab a cold one on Chicago's hottest rooftops and patios.
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Cool down on North Avenue Beach at Castaways Bar and Grill. The rooftop provides appetizers, sandwiches, fresh salads and lots of beer. (1603 N. Lake Shore Drive)
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Fulton's on the River has the ultimate patio scene right on the Chicago River. This summer they're offering new classic cocktail pitchers with flavors such as the Paloma and Red Sangria. Hit the patio from 5-7 pm each day for $1 oysters. (315 North LaSalle)
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Just when you think Wrigleyville can't handle another bar and restaurant, another one pops up to prove you wrong. Sip on a Wrigleyville Sunrise at the brand new Deuce’s & the Diamond Club. (3505 N Clark St.)
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Estate is one of the new kids on the block. By the beginning of the summer, all three outdoor spaces should be up and running, including the Sky Deck, which they claim to be the largest rooftop lounge and restaurant in the city. Oh, and it's located right on the Chicago River. (1177 N Elston)
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One of the best spots for people watching and Southern Italian fare when you're Lincoln Square is Due Lire. Try out their new Spring menu while you're there. (4520 N Lincoln Ave)
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Filini, located in the Radisson Blu hotel, is a brand new addition to the patio scene this summer. Try out the Novara Fizz (Campari, lemon juice, honey & prosecco) and try one of the signature dishes such as the Salsiccia Pizza (Fennel sausage, spicy tomato, mozzarella & garlic) (221 N Columbus Dr.)
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Frontier’s 2,500 square-foot outdoor beer garden is equipped with a bar, fireplace and a full-sized menu making it the perfect location for outdoor drinks, and casual dinners. Separated by floor-to-ceiling windows, their patio is fully winterized in case the weather gets too cool. It is Chicago after all. (1072 N Milwaukee)
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Sip on one of Gibsons's famously large martinis at either their Oakbrook or Gold Coast locations. (1028 N Rush Street and 2105 S Spring Road)
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Hub 51 not only offers great people watching from its perch on Hubbard Avenue, the menu includes delicious appetizers such as the fresh Tuna Poke or Lindsay Lohan-approved Pulled Chicken Nachos. Or sip on a pomegranate mojito or any of the cocktails from their award-winning drink menu. (51 W. Hubbard St.)
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The South Loop's Chicago Fire House was an actual fire station when it was erected in 1905. The historic courtyard once was home to the firemen's horses, but don't worry -- it's been cleaned up since, and then some. The restaurant was named "Best Steakhouse Martini" by Chicago magazine. (1401 South Michigan)
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Is there a better location for Gold Coast people watching than Hugo's Frog Bar? (1024 N Rush St.)
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Take a break from the hustle and bustle of Navy Pier and hit LandShark Beer Garden. They offer a wide selection of mixed drinks, microbrews, and refreshing frozen concoctions such as the "Miami Vice," A mix of Daiquiri and Pina Colada, with Margaritaville Premium Tequilla and rum. (Navy Pier)
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Lotties' Pub has been around for more than 78 years in Bucktown, but when you're not checking out the game or belting out karaoke, relax on the outdoor patio. (1925 W. Cortland)
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Dine alfresco style with a glass of wine at Carlucci. For nearly 25 years this establishment has provided Chicagoians a truly unique Italian experience. Sample their mouth watering Piatti Della Casa, Antipasta, or Insalante. (1801 Butterfield Road Downers Grove, IL)
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Luxbar's patio offers a picture-perfect view of the hottest corner in the Gold Coast. (18 E Bellevue Place)
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Mon Ami Gabi offers an elegant patio reminiscent of a provincial French café with views of the Lincoln Park Zoo. Try out their savory Steak Frites or refreshing Oysters Du Jour while you're out there. (2300 N. Lincoln Park West)
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Try an infused vodka or a specialty cocktail in the "Martini Garden" at Markethouse. Their American contemporary menu offers fresh, seasonal herbs, produce, meat and poultry. (611 North Fairbanks Ct. )
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If you're watching your figure, head over to Market Bar's new rooftop, the only place in Chicago serving SkinnyGirl cocktails. (1113 W Randolph)
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Mercadito is one of the hottest River North hangouts in the summer. Post up on the sidewalk patio and sip on one of the award-winning drinks such as the Pepino el Pyu. (tres generaciones blanco, cucumber, lemon, hoja santa, cumin salt) (108 W Kinzie St)
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If you find yourself at Grant Park or any other downtown events this summer, you're not too far from Mercat a la Planxa, and its sidewalk outdoor space. Try a Charred Pineapple Mojito (charred pineapple-infused rum, mint, lime juice, and soda) while you're out there. (638 South Michigan Ave)
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Prasino is a Greek word meaning "green," a sustainable vibe that fits in perfectly as you're checking out the sights along Division Street at this new Wicker Park hot spot. (1846 W Division)
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Quartino Ristorante & Wine Bar's patio offers a great perch at another of Chicago's hustlin' and bustlin' intersections. While you're not checking out the sights, dine on distinctive Italian regional specialties such as artisanal salumi, Neapolitan thin-crust pizza and house-made pasta. (626 N State St.)
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Tavern On Rush offers incredible steak and seafood on the ever-lively Rush Street. This 114 seat patio is even large enough to seat your entire pub crawl crew. Voted “Best Outdoor Dining” by Chicago Scene magazine. (1031 N Rush St)
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ROOF on theWit Hotel just unveiled a retractable roof on the 27th floor lounge, which means they're open later and year-round. Enjoy artisanal handcrafted libations and nibble on appetizers while enjoying the eye candy around you. Don't forget about the Sunday Fun Day parties during the summer. (201 N. State St.)
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Volare offers some of the finest Italian food in Chicago. Hang out on the newly-renovated patio and after a couple of cocktails you'll be able to convince yourself you're actually in Italy. (201 E Grand Avenue)
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Vertigo Sky Lounge sits on the 26th floor of the Dana Hotel & Spa, offering great views of downtown. The stylish vibe produced by their wrap-around floor-to-ceiling windows with a mixture of sofas, highboys, end chairs has attracted a long list of celebrities including Channing Tatum, Ice T and Cocco, Victoria’s Secret model Erin Heatherton, Kanye West and the Kardashian sisters. (Two West Erie Street)
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Enjoy bacon wrapped dates or creamy goat cheese baked in tomato sauce under Café Ba-Ba-Reeba's retractable roof. The relaxed ambiance accompanied with pitchers of specialty sangria is a great way to either end or begin your time out with friends. (2024 N. Halsted)
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