Rooftops in Chicago: the city of skyscrapers seen from above
A metropolis on the shore of Lake Michigan
The third-largest city in the United States by population, Chicago has about 2.7 million residents and stretches across northeastern Illinois, on the southwestern shore of Lake Michigan, one of the five Great Lakes. The Chicago River runs through it and divides downtown into three areas: the Loop, the business district bounded by the lake to the east and by the river to the north and west; the Near North Side, home to River North, Streeterville and the Magnificent Mile; and the Near South Side. The Loop takes its name from the elevated loop of the city's rapid transit system, the “L,” where nearly all of its lines meet.
The birthplace of the skyscraper
Devastated by the Great Fire of 1871, the city rebuilt itself as a laboratory of modern architecture: the Home Insurance Building, completed in 1885, is often considered the first skyscraper in history. Standing 442 meters tall, the Willis Tower, called the Sears Tower until 2009, was the tallest building in the world from 1973 to 1998. Down below, the river is spanned by dozens of drawbridges and lined by the Riverwalk, a promenade built along its banks. As for the nickname Windy City, it evokes the winds that blow in off the lake and rush between the towers.
Where to get a view from above in Chicago
The Loop and the river
Facing Millennium Park, Cindy's Rooftop occupies the 13th floor of the Chicago Athletic Association Hotel, beneath a glass roof that opens onto a terrace looking out toward the park and the lake. At the corner of Michigan Avenue and Wacker Drive, LH Rooftop spreads over the 21st and 22nd levels of LondonHouse, with a view straight down the river to Marina City. Right next door, on the 24th floor of the Art Deco tower of the Carbide & Carbon Building, Château Carbide plays up a Riviera vibe.
From the Magnificent Mile to Navy Pier
On the 6th floor of The Peninsula, Z Bar faces the Water Tower and the bustle of Michigan Avenue. In River North, Upstairs at The Gwen spreads its terrace across the 5th floor of an Art Deco hotel, within sight of the Wrigley Building's clock tower, and Bar Avec hides a shady garden on the 8th floor. At the very end of Navy Pier, Offshore Rooftop, billed by Guinness World Records as the largest rooftop bar in the world, offers the skyline on one side and the open lake on the other.
West Loop, Wicker Park, Lincoln Park and South Loop
Now one of the liveliest parts of the West Loop, Fulton Market is lined with buzzworthy restaurants: Aba and its plant-filled terrace on the 3rd floor, Cabra on the roof of The Hoxton, and The Rooftop at Nobu Chicago on the 11th floor, facing the towers of the Loop. To see the skyline in one unbroken sweep, you have to head farther out: Kennedy Rooftop takes it in from Wicker Park, The J. Parker overlooks Lincoln Park and the lake from the 13th floor of the Hotel Lincoln, and VU Rooftop views it from the south, on the 22nd floor, near McCormick Place.
Food and cocktails up high
From ceviche to sushi
On Chicago's rooftops, the food travels the world: ceviche and pisco sours at Cabra, Mediterranean mezze at Aba, miso black cod and nigiri at Nobu, and small plates inspired by Spain and Portugal at Bar Avec. American classics, from burgers and chicken wings to lobster rolls, are on the menu everywhere, and weekend brunch is a ritual at Cindy's, The J. Parker and Aba. Expect to pay up to $24 for a cocktail at Z Bar, with most spots hovering around $18 to $20, before tax and tip.
Music and nightlife
Several rooftops come alive after dark: DJs on weekends at The J. Parker and, in season, at Château Carbide; live jazz Thursday through Saturday at VU Rooftop and on Wednesday nights at The Gwen.
A rooftop for every season
Summer in the open air
Chicago winters are harsh, and some rooftops only come to life in the warmer months: Bar Avec and the Nobu rooftop close or cut back their hours when the cold sets in, then reopen once the weather warms up. For a drink on a terrace at sunset, come during the warm season, and book ahead on weekends.
Staying warm in winter
Other spots stay open year-round. Cindy's and Offshore Rooftop have their glass roofs, The J. Parker its retractable roof and VU Rooftop its glassed-in lounges. Some even turn winter into a show: heated igloos on the terrace at LH Rooftop and at Kennedy Rooftop, chalets with fireplaces at Château Carbide, and fondue and a curling lane at Upstairs at The Gwen.
Tips for enjoying Chicago's rooftops
Getting around and booking
The “L” serves most of these spots: Washington/Wabash for Cindy's, Lake for the river, Grand for River North, Morgan (Green and Pink Lines) for Fulton Market and Cermak-McCormick Place for the South Loop. Navy Pier, far from any station, is easier to reach by taxi or rideshare. Several bars are 21+ only, with ID required, and hours change from season to season: check before you go.
Photo : Matt Kieffer / Wikimedia Commons, CC BY-SA 2.0