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Updated 10:34 pm, April 14, 2016
Aire
100 W. Monroe St.
312-236-1234
Perched on the 24th floor of Hyatt Centric The Loop Chicago, this oasis in the sky offers 360 degree views of the city’s best architecture, fire pits, lush greenery, cozy couches and umbrella-topped tables for post-work maxing and relaxing. Expect a menu with small plates, handcrafted cocktails, wine and bottle service.
ETA: May 10
We’re picturing: Calling it a day at 3 p.m. and sunning ourselves until dusk


Fremont
15 W. Illinois St.
312-874-7270
A retractable roof on the second floor breathes fresh air into the River North spot, giving you all the rooftop feels late into the night. Return Saturday and Sunday mornings for a sprawling brunch buffet ($35 with an additional $15 champagne package), which includes Doughnut Vault goodies, a seafood tower, a waffle bar and more.
ETA: Open now, weather permitting
We’re picturing: Contemplating bottle service while star-gazing


GreenRiver
259 E. Erie St.
312-337-0101
Named one of our top new restaurants of 2015, GreenRiver opened with a splash last September, not leaving us much time to enjoy the sprawling outdoor terrace before winter hit. As the 18th-floor space emerges from hibernation this year, you’ll notice two separate sections: a bar area facing Lake Michigan that fits 40 to 45 and a dining area with urban views and room for 50. It will do the trick for impressing parents and out-of-town visitors.
ETA: Mid- to late April
We’re picturing: Instagramming highballs high in the sky


Joy District
112 W. Hubbard St.
312-955-0339
The folks behind Hubbard Inn gussied up the former Epic space, brought on executive chef Matt Wilde (American Junkie, Moonshine) and unveiled the new River North concept earlier this week. The best part is that the forthcoming 3,000-square-foot rooftop will feature a frozen drink program that screams happy hour.
ETA:
May
We’re picturing:
A round (or five) of strawberry daiquiris after work.

LH Rooftop at LondonHouse
85 E. Wacker Drive
312-357-1200

This is that fancy tri-level rooftop you keep hearing about, and if the renderings are any indication, it’s going to be the hottest opening of the summer. Sleek couches and manicured greenery line the historic space, which looks out over the Chicago River, Lake Michigan and Mag Mile.
ETA: Late spring
We’re picturing: A leisurely cocktail when someone else is footing the bill

25 Degrees Wicker Park
2015 W. Division St.
312-763-9600
Camp out along Division Street with a burger and spiked milkshake in hand. The new Wicker Park sidewalk patio has room for 48, so everyone’s invited.
ETA: Late April
We’re picturing: Patio-hopping through Wicker Park until we find our way home
Bonus: Dog-friendly!


3 Greens Market
354 W. Hubbard St.
312-888-9195
There’s room for 30 on the sidewalk of Brendan Sodikoff’s market-meets-coffeehouse, complete with foliage and awning shade.
ETA: Open now, weather permitting
We're picturing: Full helpings of sun to complement our burger-doughnut-tiki drink combo
Bonus: Dog-friendly!

Americano 2211
2211 W. North Ave.
773-360-8757
The former Birchwood space sprung back to life earlier this week with T.L.C. from duo Nancy Silver (Blackbird) and Chris Pappas (The Winchester). The European cafe is currently serving breakfast and lunch—dinner and bar service to follow—with the promise of a cozy, ivy-accented backyard patio coming soon.
ETA: Later this month
We’re picturing: Going H.A.M. on a scoop of Snookelfritz ice cream on a scorching-hot day


Barcocina
2901 N. Sheffield Ave.
773-687-9949
This sun-soaked 4,000-square-foot private patio seats 122 at regular and communal tables. Highlights include an outdoor bar and patio sectional for sweet summer day-drinking.
ETA: April 25, weather permitting
We're picturing: Cinco de Drinko all summer long
Bonus: Dog-friendly!

Beatrix Streeterville
671 N. St. Clair St.
312-642-0001
Streeterville, you don’t have to retreat to a rooftop for outdoor lounging. The restaurant's newest location offers patio seating for up to 100, and with a Rolodex of menus (breakfast, brunch, lunch, dinner, coffee and beyond), there’s an excuse to stay all day. Busy bees will love the market section—complete with salad and soup bars, sandwiches, sushi and hot entrees—which can also be enjoyed alfresco.
ETA: Mid-May
We’re picturing: Setting up a remote office every Friday

Black Iron Tavern
401 N. Milwaukee Ave.
312-690-4000
Alfresco game-watching is the deal at the River West elevated sports bar by Michael Taus (Taus Authentic) and Chris Johnston (Cheesie’s Pub & Grub, Whiskey Business). Along with seats for 60, expect two TVs and a projector, a fireplace and a walk-up window to the bar on the private patio.
ETA: May 1
We're picturing: Sports jerseys under button-downs for post-work burgers, beers and baseball (fingers crossed for wheelie chairs to up the fun of that bar window)
Bonus: dog-friendly


Corridor Brewery & Provisions
3446 N. Southport Ave.
773-270-4272
Sky-blue vintage metal armchairs and bench seating made from the flooring of old railroad boxcars surround reclaimed wood tables on the Lakeview brewery’s patio for 22. Green shrubbery in white antique pots and a planter box of flowers enhance the outdoor experience.
ETA: Open now, weather permitting
We're picturing: ’Tis the saison for farmhouse sips in the sun
Bonus: Dog-friendly!

Cruz Blanca
900 W. Randolph St.
We’re (im)patiently waiting for Rick Bayless’ West Loop taproom-taqueria hybrid to open its doors. In the meantime, close your eyes and imagine yourself unwinding outside with the help of Oaxacan-style tacos stuffed with red chile pork cecina and an impossibly refreshing beer brimming with local ingredients.
ETA: Summer
We’re picturing: Licking our plates clean (and not feeling ashamed) as Randolph Street swells with foot traffic


Duck Duck Goat
857 W. Fulton Market
312-902-3825
Perhaps the most highly anticipated opening of the year, Stephanie Izard’s Asian-inspired eatery in Fulton Market will offer six four-top tables for alfresco diners this spring. In other words, you’ll have to be one lucky duck to score an outdoor spot, let alone a regular reservation. Take advantage of the space with fresh picks like octopus, cucumber and peanut salad.
ETA: Mid-April 
We’re picturing: Duck eggrolls, Not Your Fortune Cookie cocktails, repeat

Earls Kitchen and Bar
1538 N. Clybourn Ave.
312-929-3952
Whether sunbathing or shade-lounging is the goal, the Lincoln Park restaurant has seats for 100 at stone tables for four (giant red umbrellas optional) and high-top tables for two. Along with an outdoor bar, there’s seating around a fire pit for those breezy summer nights after sundown.
ETA: Open now, weather-permitting
We're picturing: Sunglasses on, strawberry spritz in hand
Bonus: Dog-friendly!


Elixir Lounge and Replay Andersonville
1509 W. Balmoral Ave.
773-654-1751 and
5358 N. Clark St.
773-654-1369, respectively
Opening late last season in September, the Andersonville cocktail bar and arcade bar share this 68-seat sidewalk patio fenced in by planter boxes and accented with umbrellas and light-strung trees.
ETA: Open now, weather permitting
We're picturing: Getting old fashioned blitzed between rounds of Blitz
Bonus: Dog-friendly!


Forno Rosso
1048 W. Randolph St.
312-243-6000
Take your pie outside at the new West Loop pizzeria. With room for 60, the Randolph Street patio is apt for people watching and day-drinking. “I'm really trying to create an Italian outdoor cafe experience with fresh and light Italian handcrafted cocktails and super-light and refreshing wines,” owner Nick Nitti said. “We are also going to have a lineup of aperitif cocktails, which are an infusion of herbs and fruit in alcohol and water." Sounds dreamy.
ETA: April 15
We’re picturing: Wood-fired ’za going down easy with a glass of rosé


The Goddess and Grocer Andersonville
5318 N. Clark St.
Accessorized with turquoise furniture, string lights and planters stuffed with flowers and fresh herbs, the patio at Goddess’ imminent addition in Andersonville is fit for a slice of rainbow cake.
ETA: May
We’re picturing: Swinging by after work for a go at the salad bar and finding inner peace on the patio


Green Street Local
130 S. Green St.
312-226-6565
Flowers and fresh herbs flank the cozy 25-seat patio, creating the perfect place to explore the West Loop newbie’s extensive beer menu. If the weather turns sour, seek refuge in the multilevel, TV-studded interior.
ETA: May
We’re picturing: Swapping out sunglasses for beer goggles


Jerry's Lincoln Square
4739 N. Lincoln Ave.
872-208-6264
Trees along Giddings Plaza are expected to shade a 60-seat patio with tables for two to six at the third iteration of the whiskey bar with a respectable craft beer menu and killer grilled cheese sandwiches.
ETA: Late spring
We're picturing: Here in Lincoln Square, with my beer I sit, whilst golden moments flit
Bonus: Dog-friendly!


Johnny's Grill and Mezcaleria Las Flores
2545 N Kedzie Ave.
773-278-2215
Feel the vibes from beautiful Oaxaca on this Logan Square sidewalk patio shared by the diner and mezcaleria. With string lights and a retractable awning for those super-bright days, 100-ish people can kick back and relax with smoky Mexican-inspired cocktails and a side of pop tarts.
ETA: Early May
We're picturing: Forgetting we're still in Chicago while double-fisting clay cups of mezcal
Bonus: Dog-friendly!

The Kitchen
316 N. Clark St.
312-836-1300
Whether you’re indulging in oysters for brunch or a charcuterie plate for happy hour, this brand new 30-seat Riverwalk patio makes the perfect backdrop.
ETA: June 1
We’re picturing: Yacht-spotting over bubbly

MAD Social
1140 W. Madison St.
312-243-2097
Taking after its cozy interior, this West Loop sidewalk patio will offer industrial vibes with chic French details. Two- and four-top tables offer 20 seats to enjoy the globally influenced menu.
ETA: May
We’re picturing: Stopping in for poutine fuel before heading to United Center


Monteverde
1020 W. Madison St.
312-888-3041
West Loop’s pasta palace will flaunt a corner patio with about 20 seats on Madison and Carpenter Streets. Those floor-to-ceiling windows will open up, too, so you won’t lose your view of the pasta-making station situated behind the bar.
ETA: May
We’re picturing: Saying cannelloni saltimbocca fives times fast—after three glasses of wine


The Northman
4337 N. Lincoln Ave.
773-935-2255
Cider lovers can take their pick of sidewalk seating for 40 or a courtyard for 30 with teak tables and French woven chairs among trees and a flower garden.
ETA: Late summer
We're picturing: Along came a cider that sat down beside her
Bonus: Sidewalk seating is dog-friendly

Queen Mary
2125 W. Division St.
773-697-3522
The Wicker Park bar rooted in British maritime drinking tradition takes it outside with a 50-seat sidewalk patio populated by tables for up to eight and standing rails. The bar’s summer cocktails are fit for spring with ingredients like passion fruit-ginger syrup, peach bitters and jalapeno tincture. And the large-format tea rum punch, normally served hot, is chilled for summer.
ETA: Late spring
We’re picturing: Raising a daily grog to a boisterous “splice the mainbrace!” (that’s sailor speak for “let’s drink”)
Bonus: Dog-friendly!


Saint Lou’s Assembly
664 W. Lake St.
312-600-0600
Boozy floats, a bocce court and bleacher-style seating are all part of the package at the cafeteria dining destination’s sunny backyard patio in Fulton Market. With 100 seats, there’s room to laze around all day. Plus, enjoy select cocktails from neighboring newbie and sister spot Moneygun.
ETA: Mid-May
We’re picturing: Redeeming our high school cafeteria woes over lavender gin lemonades


Spin Chicago
344 N. State St.
773-635-9999
After taking names at the pingpong tables, head outside for custom cocktails, coffee and alfresco fare. Pro tip: Spoil your dinner with a sundae topped with seasonal fruit compote, lemongrass caramel, nutella and whipped cream.
ETA: Late April
We’re picturing: Co-founder Susan Sarandon sipping a Moscow mule on State Street

SteakBar
1500 N. Wells St.
773-966-0404
Retractable, garage door-style windows keep this new Four Corners Tavern Group and Hogsalt collaboration easy and breezy. For maximum sun exposure, ask for a spot on the 30-seat patio along the hustle and bustle of Wells Street.
ETA: Late spring
We’re picturing: Catching up with our old friends Steak Tartare and Crispy Baked Potato


Whiskey Business
1367 N. Milwaukee Ave.
773-698-7362
This whiskey watering hole is the rooftop Wicker Park has been waiting for, with seating for 170 at picnic and communal tables—some with personal ice chests for really thirsty groups—and loveseats. While brick and artificial grass walls don’t offer much of a view (and it’s a two-story building), expect five 4-by-8-foot TVs so you’ll never miss the game. Menus for both Whiskey Business and adjacent Cheesie’s Pub & Grub are available on the rooftop, along with 10 frozen margarita machines.
ETA: May 1
We’re picturing: Glistening in the sun with a shot of bourbon and grilled-cheese chaser
Bonus: Saturday morning yoga

Bernie’s Lunch & Supper
660 N. Orleans St.
312-624-9892
Because it was open for just a few short weeks last summer, this River North rooftop is considered a newbie in our book. With gorgeous wood beams overhead, string lights and dashes of springy colors, the 1,500-square-foot space is a stunner.
ETA: Next week
We’re picturing: Taking an extended lunch break that lasts ’til 5 p.m.

Best Intentions
3281 W. Armitage Ave.
312-818-1254
Behind the Logan Square neo-dive bar awaits a tropical hideout that Playboy deemed the “best patio bar in America.” A cabana bar, decorated with family heirlooms and rusted beer delivery truck panels, offers select bottled and canned beer, wine and cocktail specials. Along with perennial prairie grasses, flowers and tropical plants, the surrounding fences are lined with metal sculptures welded by the owners’ mother.
ETA: Open now, weather permitting, with full service and cabana bar opening later this spring
We're picturing: A campy vacation to Great Grandma’s Family Adventure with more booze and fewer grandmas

Cotton Duck 
941 N. Damen Ave.
773-661-6131
The West Town restaurant-art gallery combo opened last September with a BYO policy and downright enchanted patio area that's studded with flower pots, string lights and sculptures.
ETA: This weekend, weather permitting
We're picturing: Boozy date nights ahead
Bonus: BYOB


Dolce Italian
127 W Huron St.
312-754-0700
Opening in August last year, the River North Italian restaurant seats 40 on a patio separated from the sidewalk with planter boxes.
ETA: Open now, weather permitting
We're picturing: Chomping star-shaped pizzas, popping bottles of prosecco and being Italian AF


General Restaurant & Mercantile
2528 N. California Ave.
773-698-8754
The Logan Square taco saloon’s back patio levels up this season with a coming-soon game garage addition including shuffleboard, darts, table football and air hockey. There’s room for 45 on the flower-filled patio and 12 on the sidewalk bar out front.
ETA: Open now, weather permitting
We’re picturing: Wanted: competitive taco-eater proficient in air hockey.
Reward: $4 boots of craft beer
Bonus: Sidewalk seating is dog-friendly

Giardino Segreto at Osteria Langhe
2824 W. Armitage Ave.
773-661-1582
A single communal table for 14 awaits alfresco diners in the backyard of this Logan Square Italian eatery, appropriately named “secret garden” in Italian. The rustic hideaway, with romantic string lights and a garden with fresh produce and herbs used in-house, debuted in August.
ETA: Early May
We're picturing: A trip to Italy, sans airfare
Bonus: Dog-friendly!

Small Cheval
1732 N. Milwaukee Ave.
Last summer, hungry burger-slammers had to fight for a place to sit on the sunny patio at Bucktown’s baby brother to Au Cheval. Those lucky enough to score one of the restaurant's 80-ish alfresco seats can chase malort shots with a boozy milkshake under strings of star-like lights.
ETA: April 15, weather permitting
We’re picturing: Sipping peach gimlets to take the edge off that long line


To Hayati at Taxim
1558 N. Milwaukee Ave.
773-252-1558
This Wicker Park rooftop quietly debuted last August. There’s room for 80 in the Greek dinner haven, with exposed brick, a small bar and a lush garden of herbs and tomatoes in terra cotta pots that dress up the exterior of the enclosed staircase that leads to the restaurant.
ETA: May 2
We're picturing: Sharing a carafe of ouzo in the twilight with a sweetie