September 1st, 2018 by: relatedchicago

It’s peak rooftop season in Chicago, attracting pleasure hounds and dreamers alike for decadent nights and lazy days on top of the city…it’s always been that way.

flappers dancing on top of chicago

 Flappers dancing on top of Chicago Hotel, 1926

Well, almost –

Chicagoans have long had a love affair with their rooftops. In cities like Miami and Los Angeles, rooftops are obviously a big deal because they are used all year-round, but here in the Windy City – it’s a much bigger deal. Perhaps it’s because of the limited time in which we can enjoy the weather, or those unobstructed views of our magnificent skyline, the stars so close that you feel as though you could simply pluck one out of the sky, or maybe it’s just our love of a good party. Regardless, rooftops are the ultimate luxury of Chicago living and lifestyle. So, it comes with no surprise that today’s hotels and residential developers continue the tradition of reinventing ways to feed this need of ours to climb on top of tall buildings and hang out.

It’s the American dream.          

                                                                                                                                                                                                                    However, near the end of the nineteenth century, the only things that hung on a Chicago rooftop was wet laundry. At the time, real estate developers had begun to invest in apartment buildings for the rising urban-middle class, who were flocking to the city. It was the new American dream. However, this emerging demographic was not yet comfortable living in the city, on top of each other. They valued their privacy. Coming from the country, they were accustomed to living with ample space between them and their nearest neighbor. Accordingly, the new buildings were built with private entrances and staircases, in order to limit any possibility of stumbling into awkward conversations. Even balconies were rare in these buildings, and seen at the time mostly in working-class, immigrant housing.

Then, at the turn of the century, and with the advent of the elevator, buildings began to reach for the skys’. It became the new status symbol of this emerging class. Grand apartment buildings came with grander views, and rooftops and balconies were designed for full advantage. Laundry moved to the basement, and we flocked higher and higher, not only to frolic but to enjoy the fresh air and city views. Developers of the day, soon began to make use of a structure’s roof, to offer leisure activities and entertainment. It was before the advent of movies, when a fad called, theater rooftop gardens, was fashionable. It had become a staple of summertime extravagance at the time, promising entertainment and spectacle. A song called Rooftop Garden Two Step, and outlandish vaudeville acts, which showcased rooftop performers, were all the rage. During intermission, flappers imbibed and danced wildly on the buildings’ rooftops. These decadent parties went on for decades.

The friendly confines of Wrigley.            

Wrigleyville Rooftop Viewing back in the day

Wrigleyville Rooftop Viewing back in the day

                                                                                                                                                                                                                        It was around 1914 when the rooftops around Wrigley Field were first used to view Cubs baseball games. This was before big business stepped in of course, when building owners would simply invite family and friends to take in a ball game from their roof. These were small, casual gatherings. Neighborhood folks, would perch atop of what’s come to famously be known as, Wrigleyville Rooftops, lining Sheffield and Waveland Avenues. Imagine sitting on a folding chair,  a cooler filled with beer, watching Cubs gameday action in 1915. Decades later of course, an invite became an increasingly coveted prospect and building owners began constructing more and more sophisticated seating arrangements, building bleachers and charging admission to their buildings. This did not bode well with the Cubs organization at first, but after some legal entanglements, they are now officially endorsed, and the Wrigleyville Rooftops are considered a structural paradise.

Caviar wishes & airship dreams –  

Promotional picture, InterContinental Chicago, 1929

Promotional picture, InterContinental Chicago, 1929

                                                                                                                                                                                                                                    In the 1920’s the city was crazy for airships. The talk of the time was that Chicago would actually become some kind of airhub for the newest dirigibles technology. These were “lighter-than-air steerable aircrafts” that floated around the skies like ocean liners (pre-Hindenburg.) Zeppelin loading docks would span the city’s rooftops, to accommodate. Sounds amazing. Of course, this was a terrible idea, which ultimately proved totally impractical. But legend has it, that a few hotels went so far as to build blimp moorings, to appeal to their exclusive clientele, who were on a never- ending quest for the next big thing. The hotels wanted to keep up.  This never came to be, BUT it is true that the InterContinental Chicago Hotel (originally known as the Medinah Athletic Club) built a blimp mooring on top of its’, already opulent, rooftop onion dome.


The green movement   

                                                                                                                                                                                                                                             Fast forward almost a century and rooftops have become more than a leisure pursuit. Chicago has been on the forefront of the green-roof movement for more than two decades now. It ostensibly started when the city began looking for ways to actually make Chicago cooler in the summer, after a terrible heat wave in 1995 had resulted in 700 deaths.  In 2000, Chicago’s most famous rooftop garden was built atop City Hall. It features 20,000 plants from 150 different species and is credited with ushering in a new renaissance of green rooftop gardens, for which the city has become known.  It was conceived as a demonstration project and developed as part of Mayor Daley’s efforts to combat the urban heat problem, and improve air quality. The transformation of City Hall’s roof into a sprawling green space, set an ever important precedence for not only residential and commercial property owners in the city, but around the country, to follow suit. It demonstrated that green roofs do more than add beauty and sanctuary to our lives, it makes us healthier.  

 Chicago City Hall Rooftop, 2001

 Chicago City Hall Rooftop, 2001


It’s a rooftop renaissance.      

                                                                                                                                                                                                                                         And now in 2018, it’s safe to say it would be practically illegal to put up a new luxury apartment building or launch a new hotel in Chicago without a rooftop lounge – and certainly so to hang your laundry up there. These days the legacy of the rooftop lifestyle not only lives on, but is experiencing a complete renaissance. New luxury developments are being designed by the world’s leading architectural and landscape designers, and include an ever-expanding array of modern rooftop amenities, such as infinity pools and spas, sustainable gardens, summer kitchens and winter fireplaces – it’s like your own private resort.

And then there are our hotels, for which Chicago has long been known. Yet, over the last few years, we’ve been in a full-on renaissance, with a slew of new developers reimagining historic hotels and buildings with spectacular effect, each with a cooler rooftop scene than the next. Perhaps, spend an afternoon this weekend floating around one of these hotel rooftop oases.  Enjoy an Orange Blossom or some watermelon juice and the sunny skies. In about five months, this will all seem like a dream.

The Chicago Athletic Hotel (12 S. Michigan Avenue) was founded in 1890 by some of the most influential men of the time. It was an exclusive mens-only private club for more than a century, becoming one of the most highly anticipated hotel openings in the city’s history when it launched in 2015.  Enjoy an old fashioned, or a moscow mule at Cindy’s Rooftop. The hotel’s restaurant and open air terrace has insane views of Millennium Park and Lake Michigan.

The London House Hotel (85 E. Wacker) began life in 1923, as the London Guarantee and Accident Building. Decades later it was the location of The London House jazz supper club, where big names such as Sarah Vaughan and Ramsey Lewis performed. Take in the history and a cocktail at LH Terrace, which has amazing views from the center of the city.

The Viceroy Hotel (112 N. State Street)  opened this year, replacing the historic, 1920’s era Cedar Hotel. The developer incorporated the old building’s masonry and terracotta exterior, signature Chicago style elements, into the new tower. Enjoy a night at the hotel’s rooftop bar and pool area, the Devereux, complete with craft cocktails and its’ long views of the Chicago skyline.

The Robey Hotel (2018 W. North Avenue) is housed in an 1920’s office building in Wicker Park. It has maintained many vintage touches, from the preserved first-floor office directory to the Art Deco lifts. The hotel’s Cabana Club, is a rooftop lounge with a cool city vibe, boasting 180 degree views of the Chicago skyline, and a triangular dipping pool. Enjoy a margarita or a glass of rose and soak up some sun.

Hotel Lincoln (816 N. Clark Street) was built in 1928, and went through a century’s worth of iterations before being reborn again in 2012. The rooftop hotel bar and restaurant, J. Parker, features an outstanding view of Chicago.

London Calling, LH Terrace, 2018

London Calling, LH Terrace, 2018



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