After another long winter, it’s finally feeling like summer in Chicago. Why not celebrate the warmer weather by enjoying one of our city’s iconic views while sipping something special?
Here are our 10 favorite places to take advantage of everything this beautiful metropolis has to offer, while also savoring some of the finest wines, cocktails, and brews in Chicago.
Streetervile Social
Streeterville
Surround yourself with the Chicago skyline by imbibing at the Streeterville Social, located just off the Magnificent Mile atop the Loews Hotel. Inspired by all-things summer, expect creative cocktails, delicious eats, and even boozy freezer pops to send you right to childhood.
The perfect balance of a casual and classy, relax on one of their many couches while sipping a Bee’s Knees (made with local honey) while nibbling on delicious small plates, or play lawn games like giant Jenga or cornhole. What sounds more like summer than that?
North Pond
Lincoln Park
Located literally inside gorgeous Lincoln Park, this Michelin star restaurant promises a date night to remember. Dine on some of Chicago’s top cuisine paired perfectly with high-quality wines, all while overlooking the park’s iconic—you guessed it—North Pond.
320 RiverBar
Near North Side
Searching for an incredible happy hour with a distinctively Chicago view? Located right along the River, 320 RiverBar is an absolute can’t miss! Soak up that sunshine and enjoy drink (or three) al fresco with insanely affordable local beers, cocktails and wine every day from 3:20–6:20.
With gastropub fare like burgers, flatbreads, and salads, this casual eatery is the perfect people pleasing destination.
Apogee
River North
Now for something a little different. With their ridiculously creative cocktails served in quirky “glasses” like bamboo shoots or ceramic mushrooms, don’t be fooled into thinking it’s all gimmick. The master mixologists at Apogee serve some of the best drinks in the city all on the rooftop of the Dana Hotel.
A true treat for all of your senses, be sure to try the Fibonacci, served in an actual seashell, or the refreshing vodka-based Nymph with an elegantly floating flower. With a cozy firepit and ample space indoors, Apogee is a great even when the temperature dips and a perfect spot for groups, because why not share the spectacle?
Cindy’s
The Loop
Whether you’re a lifelong local or a first-time visitor, Cindy’s is the place if you want to truly feel like you’re in middle of it all.
Sip on one of their signature cocktails like the refreshing Grey Gardens or the aromatic Kotodama and take in everything the Second City has to offer. Steps from Millennium Park, overlook some of Chicago’s most iconic sights including the Bean, Maggie Daley Park, Lake Michigan, and our iconic skyline.
City Winery
RiverWalk
If people watching is your favorite kind of view, City Winery is a can’t miss. Located right on the Chicago River in the West Loop, casually sip your favorite rosé while watching yachts cruise by and pedestrians wander down the Riverwalk.
And don’t let winter keep you from enjoying a glass. As the temperature dips, City Winery sets up climate controlled “igloos” allowing guests to enjoy outdoor dining, no matter the season.
Deveraux
Gold Coast
Smack dab in the heart of the Gold Coast sits this intimate, swanky lounge. Take in unparalleled 18th floor views day or night while sipping impeccably crafted classic cocktails poolside. Or with floor-to-ceiling windows, you can enjoy everything this gem has to offer even if the weather decides to be fickle.
The Up Room
Wicker Park
Sometimes the best skyline views are from the outskirts. Cue the Up Room — a trendy rooftop bar located a few miles from the Loop in Wicker Park.
Situated on the 35th floor of the Robey Hotel, this cozy space not only boasts expertly crafted cocktails and a long wine list, but also never-ending vistas of the entire Chicagoland area from the downtown cityscape, all the way to the neighboring states.
Signature Room at the 95th
Streeterville
There’s no debating the epic view that the Signature Room offers. High atop 875 North Michigan, dining here promises a romantic evening that impossible to replicate. Offering classic cocktails, elegant plates, and a diverse wine list, look down on Chicago from your own classy perch in the sky.
Castaways Bar & Grill
Lincoln Park
Who says you can’t enjoy a great seaside bar in the Midwest? Just head to North Avenue Beach, look for a boat docked in the sand, and you might as well be lounging in Mexico.
With a breathtaking view of Lake Michigan and water so close you can smell it, Castaways is perfect for a fun, casual summer day. This isn’t the place for top-shelf martinis. Instead, order a piña colada or beer bucket, soak in that lake breeze, and transport yourself back to spring break.
Now that summer has started to move in to Chicago, these outdoor bars and restaurants are a great way to spend a nice evening in the city.
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