IN A BUSTLING city full of big-shouldered skyscrapers, it can be easy to feel a bit claustrophobic. But if that bustling city is Chicago, you’ll thankfully find a slew of opportunities to rise above it all, literally.
The iconic Willis Tower (formerly the Sears Tower) was the tallest building in the world when construction was completed in 1973, a brag it held onto until the late 1990s. Today, it still holds rank for its Skydeck observation platform on the 103rd floor. Perched at 1,353 feet, it’s the highest public viewing platform in the U.S., besting even One World Trade Center in New York City. On a clear day, you can see four states: Michigan, Indiana, Wisconsin, and, of course, Illinois. Feeling brave? Step out onto The Ledge, the west-facing glass-bottomed balcony, and look straight down to South Wacker Drive and the Chicago River. Not to be outdone, 360 Chicago is home to Tilt, a daring attraction that slowly cantilevers plucky participants over the Magnificent Mile from 94 stories up. If you need a little liquid courage, CloudBar on the same floor is a lofty setting for cocktails overlooking Lake Michigan. Meanwhile, the perennial favorite Centennial Wheel at Navy Pier spins riders around in an enclosed gondola at heights reaching nearly 200 feet.
Cap off your high-altitude escape by hopping on a helicopter tour of Chicago’s famous landmarks with Vertiport Chicago. Prefer to keep your feet on solid ground and leave the skies to the professionals? Head to the annual Chicago Air and Water Show on the lakefront on August 15 and 16. The largest free event of its kind in the country, it’s a unique chance to witness impressive aerial acrobatics by stunt flyers and precision military teams.
DISTANCE: 183 miles
DRIVE TIME: 3 hours
FLOAT ON. The EmotionAir Balloon Museum fills The Fields in Logan Square with giant installations.
STAY. In Wicker Park, the art deco–style Robey hotel boasts panoramic views of the skyline along with an intimate pool scene on the sixth floor and the swanky Up Room lounge on the 13th.
EAT. Feast on oysters, truffle fries, and duck pie under the atrium of Cindy’s Rooftop.
