Revel in the sunshine or see the skyline at sundown from atop terraces that come in all different heights. You can almost touch the iconic Wrigley Building clock tower from Terrace at Trump, situated right at the bend of the Chicago River on the 16th floor of the Trump International Hotel and Tower.
Connected to beautiful Millennium Park just across the Nichols Bridgeway, Terzo Piano offers artful surroundings to enjoy the signature cuisine of Chef Tony Mantuano. The seasonal menus are Italian, with a modern focus - very fitting considering the terrace extends from the third floor of the Modern Wing at the Art Institute of Chicago.
Dine on dim sum in luxury at Shanghai Terrace, the fourth floor oasis in the Peninsula Hotel Chicago that recreates a 1930s supper club, complete with authentic Cantonese cuisine and decadent cocktails.
For a more casual elegance, NoMi Garden is a lively and lush landscaped terrace nestled just off the Gold Coast on the seventh floor of the Park Hyatt Chicago.
Neighborhood favorites include Davanti Enoteca in Little Italy for their rustic small plates and cozy 45-seat rooftop deck and the sprawling veranda at Pegasus in Greektown with unobstructed views of downtown.
Watch the boats cruise along the Chicago River and Lake Michigan as rays reflect off the gentle waters. Along the LaSalle Street and Clark Street bridges, spread out on spacious esplanades below street level, Fulton's on the River and Bridge House Tavern offer downtown views from the river's edge that are uniquely Chicago.
Casual alfresco dining and fresh seafood selections are the specialty at Navy Pier's Riva Café. Less formal than its upstairs sibling Riva Crab House, the open air views and relaxing atmosphere are the perfect way to take in the evening Lake Michigan fireworks displays.
And for the most laid back fun, beach wear is welcome at Castaways Bar and Grill. Refuel with the full menu of grill standards and light summer fare and catch some sun from the upper patio deck of this boathouse on North Avenue Beach.
Warm weather draws out the crowds, making a sidewalk seat the best way to feel like you're part of the city's summertime energy. The place to see and be seen, Tavern on Rush is a Gold Coast staple where locals and visitors rub elbows with politicians and celebrities. Competing for attention between the menu's steaks and chops is the lively street scene that takes over at the confluence of Rush, State and Bellevue.
Quartino, centrally located in River North, is a fantastic gathering space for couples and groups alike. If their charming bistro seating on the patio doesn't lure you in, maybe their motto will - "Where the wine is cheaper than water and the pizza is the finest."
Look out from the tasteful sidewalk patio at the Irish-owned restaurant The Gage and iconic Millennium Park dazzles from across the way. Behind the handsome facade of its historic building, the talented kitchen - led by Executive Chef Dirk Flanigan - turns out upscale comfort food that is a long way from pub grub.
And don't miss any of the popular neighborhoods outside the central downtown, where tons of foot-traffic makes for prime people watching. Lincoln Park is a great outdoor destination in itself, with the picturesque park and its weekly Green City Market. But an added reason to visit is for the garden fresh creations from Chef Paul Virant at Perennial Virant.
On the other sides of town, pass storefront galleries and independent shops and eateries to find the curbside seats at Lula Café in Logan Square and Nightwood in the east Pilsen arts district. Here, eating local never tasted so good, and sitting outdoors among neighbors only heightens the dining experience and sense of community.
Dining on a patio can mean many things in Chicago - a hidden garden haven, a skinny pedestrian walkway, even a former mechanic's garage parking lot. At Piccolo Sogno, the glorious green garden is truly a "little dream" as its name suggests. Sheltered from the hustle and bustle of River West, it invites you to settle into quiet conversation and enjoy the rustic Italian menus and romantic scenery.
For "Cheese, Swine & Wine" look no farther than the Purple Pig, where the patio is set off just steps from the Mag Mile on an elevated walkway adorned with purple umbrellas and twinkling lights. A covered tent and heaters warm up guests when the temps cool.
Also downtown near Michigan Avenue, the roomy Plaza at Park Grill buzzes with energy, matching the vibrant scene of Millennium Park that surrounds it. What becomes an ice skating rink in the winter is the city's largest al fresco dining space in the warmer months, where visitors and locals sit beneath "the Bean" and dine on casual fare with Chicago flair.
On a peaceful little stretch of Halsted Street sits the stylish BOKA Restaurant. The idyllic Lincoln Park neighborhood makes a sophisticated setting for the modern cuisine of Chef Giuseppe Tentori and the back and front patios are framed by lovely foliage and private fencing.
Combining street food, whiskey and the ultimate people watching scene, Big Star in Wicker Park takes taco takeout to a whole new level. Expect loud music and a good crowd to spill out from this utilitarian corner patio - and like at many outdoor destinations, plan to wait for a table.
Terzo Piano article photo courtesy of Jeff Kauck