A mighty metropolis renowned for its world-class museums, fine restaurants and frankly epic city skyline, the Windy City is, if anything, even more thrilling at night. There’s an absolute abundance of attractions and activities worth staying up late for, from galleries and ghost tours to deep dish pizza and old-school jazz joints. Hop aboard for our whistle stop guide to some of the best things you can do in Chicago at night time.
Skyline Views
Chicago’s sensational skyline is the envy of cities across the States. Take a leisurely evening stroll along Lake Shore Drive or the Chicago Riverwalk and you’ll soon find out why. We’re talking soaring skyscrapers that include the awesome Willis Tower (for many years the tallest building on the planet, fact fans) and the iconic neo-gothic Tribune Tower. Incredible enough to look at during the day, these architectural titans really come into their own by night, lighting up to produce one of the world’s most recognizable cityscapes. See them from the water on a night cruise of Lake Michigan, when widescreen views of the illuminated city reflect beautifully in the glassy waters that lap the shoreline.
Head in the Clouds
You’ve checked it out from ground level, now take in birds’ eye views from atop some of the Western world’s loftiest skyscrapers. You need nerves of steel to ascend to Skydeck Chicago atop the Willis Tower. At 1,353 feet and 103 floors up, it’s only the highest observation deck in the United States. No wonder then that you can see four states from up here, as well as Chicago landmarks including Navy Pier, Lake Michigan and the Magnificent Mile. Daredevils/masochists can even step out onto The Ledge to see the lights of the Windy City twinkling far beneath their feet. A little closer to terra firma at a mere 1,030 feet up, 360 Chicago adds the option to experience TILT, a sky-high thrill ride in which willing victims participants climb onto a moving glass platform which then – yup, you guessed it – tilts riders forward to a perilous angle over the city. Very much not for the faint of heart.
Bean There, Done That
For a unique perspective on the iconic Chicago skyline, hit up The Bean on the AT&T Plaza at Millennium Park. This huge stainless steel sculpture by British artist Anish Kapoor – officially named Cloud Gate, but more commonly known as The Bean due to its shape – has quickly become a Windy City icon. Visit at night, when the bright lights of the Michigan Avenue skyscrapers reflect on its gleaming surface, creating hallucinatory magic-mirror cityscapes that bend, twist and morph as you walk around and underneath it. Check listings for al fresco evening concerts elsewhere in Millennium Park during summer.
Take a Tour
There are dozens of ways to get under the skin of night time Chicago without, you know, the tedium and inconvenience of poring over a guidebook for hours. Take to the skies on a twilight helicopter tour over Lake Michigan and that famous city skyline; hear all about the Windy City’s ghosts and gangsters on a spooky walking tour; or – perhaps best of all – join a foodie tour that gives you the chance to tuck into unmissable local delicacies such as Chicago-style hot dogs, Italian beef sandwiches, and deep dish pizza. Yum.
Museum Lates
Chicago has a frankly superb selection of museums and galleries, many of which have regular late opening hours, allowing you to ogle Old Masters, contemporary masterpieces and ancient artifacts in relative peace and quiet. Hit up the Art Institute of Chicago on Thursday evenings, when you can check out significant pieces from Hopper, van Gogh, Picasso, Matisse, O’Keeffe and more until 8PM. Other Windy City institutions including the Chicago History Museum and Museum of Science & Industry run ‘happy hour’ events that run as late as 10PM, and the Adler Planetarium’s late Wednesday openings provide a stellar option for whiling away chilly winter evenings.
Animal Magic
Museums and galleries a little too stuffy for you? Fear not! Take an evening walk on Chicago’s wild side at the Lincoln Park Zoo where, on balmy summer evenings, the park stays open late for adult-only events that include the likes of wine festivals and craft beer tasting. There’s nothing quite like the roar of a nearby African lion or cackle of a laughing kookaburra to get the party started. Meanwhile over at the Shedd Aquarium, night time events for adults include animal encounters, cocktail evenings and salsa classes, though not necessarily all at the same time.
Navy Pier
A tad nippy in winter, but a vibrant waterfront treasure on summer nights, Navy Pier is where it’s at for old-school seaside-style vibes. That’s largely thanks to the fab Ferris wheel that dominates the shoreline here, but after-dark firework displays, buzzy rooftop bars, live music, fab fast food joints and delectable dessert stores all add to the fiesta atmosphere. Grab an original rainbow ice cream (that’s orange sherbet, pistachio, Palmer House, chocolate and strawberry stacked high on a cone) and tuck in as the sun sets over the water.
All That Jazz
Hipster joints abound in downtown Chicago, and the Green Mill Cocktail Lounge, with its distinctive lime green neon sign, should be at the top of every bucket list. This century-old Chicago institution was once a favorite of Al Capone and his band of bootleggers, who used tunnels underneath the bar to smuggle booze during Prohibition. So grab a seat in Capone’s old booth, order up a Manhattan, and enjoy some of the finest jazz acts in town, just like Big Al used to do. Blues fans are also well-served in Chicago, thanks to the likes of Kingston Mines, Buddy Guy’s Legends and the House of Blues, while scuzz-rockers can get their fix at hipper-than-thou dive bars including Pilsen’s beloved Skylark and the Rainbo Club in Wicker Park.
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