Chicago's Best Al Fresco Happy-Hour Spots

Photo: Courtesy of Osteria Langhe.
If you've been following the news, then you know we are just a signature away from the return of happy hour in Chicago — and the timing couldn't be more perfect. What better way to celebrate the winning combo of summer weather and drink specials than with a refreshing cocktail at one of the city's best outdoor spots?

From cozy, tea-light-lined patios and gardens to sidewalk cafés and scenic rooftops, these al fresco drinking destinations all deserve a place in your regular rotation. We also threw in a few not-super-busy picks and sleepers that are destined to become your new happy-hour haunts. Bottoms up!

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Photo: Courtesy of Expat.
Just in time for patio season, Element Collective, the brains behind Kinmont and Nellcôte, has opened Expat, an al fresco-only, 24-seat sidewalk café on Green Street in the West Loop. The casual spot serves up boozy limoncello, rosé and sidecar sno-cones, refreshing cocktails, crudités, and light crudos like the aguachile verde with raw shrimp, cucumber, and serrano. Oh, and don’t forget the fun shot pairings (vodka, strawberry lemonade; tequila, sangria) — perfect for happy hour outdoors!

Expat, 118 North Green Street (between Randolph Street and Washington Boulevard); no phone listed.
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Photo: Courtesy of Ramen-san.
No, you don't have to order a steaming bowl of brothy noodles in the middle of summer. Chef Doug Psaltis' cold Chuka Ramen comes in a chilled dashi with heirloom tomatoes, cucumber, fresh-grated wasabi, toasted nori, and thinly sliced, seared tuna — it's like an Asian gazpacho with your blast-chilled Asahi beer. The 16-seat, intimate patio features high-top communal seating and umbrellas for extra shade. Sweeten the deal with a strawberry-and-cream shaved ice.

Ramen-san, 59 West Hubbard Street (between Clark and Dearborn streets); 312-377-9950.
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Photo: Courtesy of The Promontory.
The Promontory
This Hyde Park newbie offers a refuge from the concrete jungle with its two 45-seat outside areas, including a first-floor patio with a fire pit and a second-floor lounge open during music events. Beverage manager Dustin Drankiewicz and sommelier Diana Hawkins teamed up to create their take on a wine cooler with German riesling, Spanish rosé, organic strawberries, and lemon. Pair it with happy-hour-friendly small plates like fava-bean agnolotti with morels and crispy chicken skin, or the P.E.I. mussels with merguez sausage cooked on the restaurant’s hearth fire pit for extra smokiness.

The Promontory, 5311 South Lake Park Avenue (between 53rd and 54th streets); 312-801-2100.
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Photo: Courtesy of Loews Hotels.
Streeterville Social, Loews Hotel
Looking to play a little bocce ball with your after-work snacks? Streeterville Social, the new rooftop terrace at the Loews Hotel, has a grassy lawn area for sun-soaking and a game of pétanque (bocce's French cousin). Or swing from the birdcage chairs in the cabanas at either of the terrace's two bar areas. Executive Chef Mark Payne serves up a menu of refined street food, including an oyster po’ boy with cioppino broth, chorizo, and roasted-garlic aioli, alongside summery cocktails like the Streeterville Mai Tai or a glass of rosé from one of the many bubbling and still varieties on the "Pink Page."

Streeterville Social, 455 North Park Drive (between Illinois and North Water streets); 312-840-6600.
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Photo: Courtesy of The Duck Inn.
The Duck Inn
Chill in the lush, multilevel backyard at this Bridgeport hotspot and the Rockit Ranch Productions’ latest concept. Ex-fine-dining chef Kevin Hickey gets casual with a bar-snacks menu that plays off Chicago classics, like his Hamburger Sandwich (dijonnaise, Brun-uusto cheese, rye) and the Duck Fat Dog (Chicago-style, instant pickle), reminiscent of his popular dog he once served at the Four Seasons' Allium. Many of the craft brews on tap were made specially for the restaurant by local breweries.

The Duck Inn, 2701 South Eleanor Street (between Short and Loomis streets); 312-724-8811.
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Photo: Courtesy of Piccolo Sogno Due.
Piccolo Sogno Due
This 34-seat, street-side patio will make you feel like you're dining at an outdoor Italian café, only downtown. Located steps away from the Chicago River and many office buildings, this sleeper happy-hour spot serves up light, small plates for summer — from an herbaceous grilled octopus with roasted peppers and fingerling potatoes to pizza bianca with fresh mozzarella and arugula. Wash it down with one of the many wines by the glass or a refreshing cocktail like the Acca Larentia with vodka, St. Germain, and lime juice.

Piccolo Sogno Due, 340 North Clark Street (between Kinzie Street and the Chicago River); 312-822-0077.
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Photo: Courtesy of Celeste.
Grab a seat on the fourth-floor garden patio for classic cocktails and bites by consulting chef Nick Lacasse. Set in an 1888 Louis Sullivan building that was once a glass factory, the patio maintains some of the historic look with exposed brick, white leather, antique-looking chairs, and decorative shrubbery. Pair the perfectly slow-cooked and lightly grilled octopus with romesco sauce, chickpeas, and crunchy radish with the Dear Valencia cocktail, a Plymouth Gin-based drink with dry vermouth, Meyer lemon, celery, and sriracha for extra spice.

Celeste, 111 West Hubbard Street (between LaSalle and Clark streets); 312-828-9000.
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Photo: Courtesy of Tanta.
Now with a new retractable canvas cover, this popular rooftop spot just got better. Chef Jesus Delgado expanded the special outdoor snacks menu with five sections featuring different ceviches, causitas, anticuchos, empanadas, and three new soy-spiked del chifa dishes, along with vegetarian and entrée-size selections. Try the Tanta ceviche with scallops, shrimp, and a creamy rocoto-aji amarillo sauce or the anticuchera causitas with octopus, avocado, quail egg, and piquillo pepper. Nothing goes better with Peruvian food than a frothy pisco sour or the famous El Chignon cocktail with Tanteo jalapeño tequila, mezcal, lime, rocoto-pepper-infused ice, and cilantro.

Tanta, 118 West Grand Avenue (between LaSalle and Clark streets); 312-222-9700.
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Photo: Courtesy of Little Goat Diner.
Little Goat Rooftop
Little Goat Rooftop combines the best of Little Goat’s laid-back vibe with cozy couches and sweeping downtown views. Grab a cocktail from the bar to sip with snacks like seasonal ceviches, olives, or chef Stephanie Izard’s goat-liver mousse for a heartier happy-hour “meal.” Note: The rooftop closes during private events, so check for openings online.

Little Goat Diner, 820 West Randolph Street (between Green and Halsted streets); 312-600-6090.
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Photo: Courtesy of Parlor Pizza Bar.
Parlor Pizza Bar
Snack on pizza earlier in the evening at this bustling bar with a sprawling outdoor patio and, new this year, a rooftop deck seating 150 and featuring a full bar built out of an old freight-shipping container. With 14 pizzas — from classic Margherita to a burrata-topped pie and one with house-made sausage and roasted red peppers — all complemented by a vast craft-beer selection, you can come for happy hour after work and stay late.

Parlor Pizza Bar, 108 North Green Street (between Randolph Street and Washington Boulevard); 312-600-6090.
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Photo: Courtesy of The Betty.
The Betty
This West Loop newbie now serves its inventive cocktails and small bites outside on the 40-seat patio enclosed by wrought-iron fencing intertwined with green ivy and purple alyssum flowers. Veteran mixologist Peter Vestinos created the cocktail list with summer-friendly sips like a classic gimlet with gin and house-made lime cordial and the Maximillon with tequila, ancho-chile liqueur, and sparkling wine. Pair them with light bites like potato-and-mushroom pierogis, croquettes, and kampachi crudo with mussels.

The Betty, 839 West Fulton Market (between Green and Peoria streets); 312-733-2222.
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Photo: Courtesy of The J. Parker.
The J. Parker
Set atop the Hotel Lincoln, this bar and restaurant overlooking Lincoln Park and the zoo has some of the best views in the city, with Lake Michigan to the East and the skyline to the South. A newly installed retractable glass-roof covering now makes it possible to enjoy the 140-seat space, rain or shine. Come with a group to sample the upscale bar food developed by chef Paul Virant, from mini-burgers with dry-aged beef, butterkäse cheese, and pickle relish to edelweiss-cheese fritters with cherry aioli. Mixologist Allie Kim whips up seasonal cocktails that change as new herbs and fruits show up at the farmers' market.

The J. Parker, 1816 North Clark Street, 13th Floor (between Lincoln Avenue and Menomonee Street); 312-222-9700.
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Photo via @oakandchar.
Oak + Char
This River North up-and-comer added a new 56-seat, street-side patio with custom-made wooden tables and chairs and overhead bulb lighting. You can’t go wrong with the local burrata and heirloom tomatoes with grilled toast and watermelon vinegar, while the “MSG” wings made with maple, sherry, and gochujang chili continue to be a fan fave, especially when paired with after-work drinks.

Oak + Char, 217 West Huron Street (between Franklin and Wells streets); 312-643-2427.
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Photo: Courtesy of Boka.
This lush terrace in the heart of Lincoln Park has two six-person tables set in a picturesque space created by landscape-design firm Bottle & Branch. With hanging flowers, fence-lined greenery, and rows of herbs planted into the center of each table, you’ll feel like you’re celebrating happy hour in the middle of a garden. Enjoy Michelin-starred chef Lee Wolen's cold and hot small plates (marinated blue marlin, smoked foie gras, brandade ravioli) alongside creative cocktails and a well-thought-out wine list.

Boka, 1729 North Halsted Street (between Willow Street and North Avenue); 312-337-6070.
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Photo: Courtesy of Osteria Langhe.
Osteria Langhe
Totally underrated, this sleeper restaurant serving authentic Piedmontese fare at the edges of Logan Square has a charming, string-lighting-lined street-side patio, making the perfect setting for a super-classic and refreshing orange-spiked Negroni. Pair it with chef Cameron Grant's fresh, shareable dishes like tuna tartare, thinly shaved veal with creamy tonnato sauce, and tender octopus in a leek-infused vichyssoise. Or try the pan-roasted halibut with a summery salad of cherry tomatoes and microgreens.

Osteria Langhe, 2824 West Armitage Avenue (between California Avenue and Mozart Street); 773-661-1582.
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Photo: Courtesy of Unite Urban Grill.
Unite Urban Grill
Watch the world go by from this West Town spot’s street-side patio on Chicago Avenue while enjoying the robust "snacks" section, perfect for happy hour. Try the shareable lamb meatballs with fava-bean-and-corn succotash, asparagus, Calabrese-chili aioli, mint, and micro-scallions. They go great with a glass of rosé or one of the specialty cocktails named after Chicago neighborhoods, such as the Wicker Park, made with mezcal, cherry liqueur, and lemon.

Unite Urban Grill, 1450 West Chicago Avenue (between Greenview Avenue and Bishop Street); 312-455-8900.

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