How to Make the Most of Your Chicago Layover

Catch an eyeful of the Windy City.

By Hannah Lott-Schwartz

Each year, nearly 80 million travelers pass through the Windy City’s Chicago O’Hare International Airport, the sixth-busiest in the world. Though you’ll need a layover on the longer side to get to downtown and back (say, a minimum of five hours to play it safe), the “L” train is a relatively easy and inexpensive way to dip your toe into Chicago; it’s just $10 for an unlimited day pass. While a city as diverse as Chicago has all manner of attractions to discover, when time’s limited, the Loop—Chicago’s official downtown—is its highlight reel.

Park Time

From the airport you can hop on the Blue Line and head to Millennium Park (201 E. Randolph St.), a celebrated public space that’s considered one of the Midwest’s top attractions, where grand art meets iconic architecture. After you snap a selfie in the mirrorlike surface of Anish Kapoor’s giant Cloud Gate, also known as the Bean, you can explore the Frank Gehry–designed Jay Pritzker Pavilion (201 E. Randolph St.; concert prices vary) reflected in the Bean. This stunning display of deconstructivism offers free cultural programming throughout the year and also hosts the Chicago Jazz Philharmonic, theater performances, and multiple music festivals. At the south end of the park, you can lose hours in the Art Institute of Chicago (111 S. Michigan Ave.; 312-443-3600; adults, $25; seniors and students, $19), the nation’s second-largest art museum and home to such famed works as Grant Wood’s pitchfork-wielding couple in American Gothic, Edward Hopper’s Nighthawks diner scene, and Georges Seurat’s pointillism masterpiece A Sunday on La Grande Jatte.

Get Cultural

Next you can head to Michigan Avenue, better known as the Magnificent Mile, where you might earn a worth-it crick in your neck inside the Chicago Cultural Center (78 E. Washington St.; 312-744-3316) from ogling its magnificent domed ceiling, a glittering mosaic of 30,000 Tiffany glass tiles. If the timing works out, opt for a free hour-long tour of the 1897 building, which was the city’s first library. Then you can continue strolling north, detouring along the Riverwalk (Michigan Ave. at E. Upper Wacker Dr.), a one-and-a-quarter-mile path that blends urban scenes with recreation. From here you can cross the Chicago River via the DuSable Bridge, an engineering feat that has been raised for boats to pass beneath since 1920.

On the other side, you can pay tribute to the Tribune Tower (435 N. Michigan Ave.), a Gothic Revival wonder that’s being turned into condos after housing the Chicago Tribune for nearly a century. But the tower’s very fabric remains imbued with legend. Stones embedded in its exterior memorialize famed buildings from around the world, while the lobby doubles as the Hall of Inscriptions, with quotes extolling freedom of the press from Voltaire, Benjamin Franklin, and others covering the walls.

Drinks With a View

By now it’s time to rest your feet. Do so 1,000 feet in the air at The Signature Room at the 95th (875 N. Michigan Ave.; 312-787-9596; drinks for two, $20), the fee-free alternative to the observation deck one floor below at 360 Chicago and a (mostly) line-free alternative to the Skydeck’s well-tracked transparent floor. While a beer will set you back $10, the lounge has a relaxed dress code and comes with a bird’s-eye view of the Windy City—perhaps a more comfortable, lasting version of the one you’ll get as your flight whisks you away to your final destination.

  • NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
  • Published: October 2018