Chicago's Most Iconic Landmarks

Willis Tower, known for most of its life as the Sears Tower, is the black-aluminum-and-bronze-glass giant that anchors the western edge of the Loop. Designed by Bruce Graham and structural engineer Fazlur Rahman Khan of Skidmore, Owings and Merrill, it introduced the bundled-tube structural system, a cluster of nine square tubes rising to different heights that made unprecedented altitude both economical and stable. That innovation is why the tower's silhouette steps back as it climbs, and why it held the title of world's tallest building for a quarter century.

The public heart of the tower is the Skydeck on the 103rd floor, one of the highest observation decks in the country. On a clear day the view reaches across the flat Midwestern grid to four states and out over the immense blue plane of Lake Michigan. The signature experience is The Ledge, a series of glass boxes that cantilever out from the building so that you stand on transparent floor with nothing but air and more than a thousand feet between you and the street.

Beyond the thrill, the Skydeck is a lesson in how Chicago reads from above: the river forking through downtown, the regular march of Burnham's street grid, the green lakefront parks, and the newer towers crowding the near riverbanks. Interpretive exhibits on the way up trace the building's engineering and the city's history, giving context to the panorama that follows.

The Wrigley Building rises at the foot of the Magnificent Mile, where Michigan Avenue crosses the Chicago River, built as the headquarters of the chewing gum empire founded by William Wrigley Jr. Designed by Graham, Anderson, Probst and White, its two towers are clad in glazed white terracotta that grows subtly brighter toward the top, a deliberate trick to make the building shine against the sky.

Its form borrows from the Giralda tower of Seville Cathedral, crowned with an ornate clock and a spire, a nod to the eclectic historicism popular in the 1920s. The building's most theatrical feature is invisible by day: after dark it is bathed in floodlights, a practice begun in the 1920s that made it one of the first illuminated skyscrapers and a nightly landmark for river traffic and pedestrians alike.

The Wrigley Building forms an unforgettable gateway pairing with the Gothic Tribune Tower just across the avenue, and its plaza and pedestrian bridge over the river are among the best places in the city to understand how architecture, water, and boulevard come together. The building remains a working commercial address, and its ground-floor spaces and courtyard welcome the public to pause beneath the glowing terracotta.

The Art Institute of Chicago faces Michigan Avenue behind its two famous bronze lions, an encyclopedic museum whose collection spans five thousand years and nearly every corner of the globe. The original Beaux-Arts building was raised for the World's Columbian Exposition of 1893, and the museum has grown through many additions, most recently the light-filled Modern Wing designed by Renzo Piano.

It is celebrated above all for its Impressionist and Post-Impressionist holdings, one of the finest anywhere, where you can stand before Georges Seurat's monumental A Sunday on La Grande Jatte, a room of Monet's haystacks and water lilies, and works by Renoir, Caillebotte, and van Gogh. The American galleries hold Grant Wood's American Gothic and Edward Hopper's Nighthawks, two of the most reproduced paintings in the country, often surprising visitors who did not realize they live here.

Beyond the famous canvases, the museum is a universe: ancient Greek and Roman art, a superb Asian collection, medieval armor, the reconstructed Chicago Stock Exchange Trading Room by Louis Sullivan, and the miniature Thorne Rooms beloved by children. The scale rewards both a focused visit to a few masterpieces and a full day of wandering, and the Modern Wing's bridge and terrace offer fine views back toward Millennium Park.

Buckingham Fountain sits at the center of Grant Park, one of the largest fountains in the world and the ceremonial heart of Chicago's front yard. Designed by Edward Bennett and inspired by the Latona Fountain at Versailles, it was a gift from philanthropist Kate Buckingham in memory of her brother, rendered in pink Georgia marble on a grand rococo scale.

The fountain is meant to symbolize Lake Michigan, with four pairs of bronze sea horses representing the four states that border the lake. During its display season it performs on a regular cycle: a spectacular major eruption sends the central jet soaring roughly a hundred and fifty feet into the air, followed by quieter interludes, and after dark the whole basin is lit with a choreographed show of colored lights set to music.

Set against the open sky and the lake beyond, the fountain is a favorite gathering point and a classic Chicago postcard, familiar to many as the opening image of a long-running television series. Surrounded by the formal lawns and rose gardens of Grant Park, it makes an elegant centerpiece for a lakefront stroll and a fine vantage for taking in the skyline rising to the west.

The John Hancock Center, now officially 875 North Michigan Avenue but forever the Hancock to Chicagoans, is the tapering black tower whose exterior X-braces are among the most recognizable structural expressions in the world. Like Willis Tower it came from Skidmore, Owings and Merrill and the engineering mind of Fazlur Rahman Khan, whose trussed-tube system let the building rise a hundred stories while using dramatically less steel.

Those visible diagonal braces are not decoration: they carry the wind and gravity loads to the corners, allowing the slender, tapering profile and freeing the interior of many columns. The building pioneered the mixed-use vertical city, stacking parking, offices, and apartments in a single tower, so that residents could live near the top of one of the world's tallest buildings.

The public draw is 360 Chicago, the observation deck on the ninety-fourth floor, whose position right on the Magnificent Mile gives it a more intimate, lake-hugging view than towers deeper in the Loop. Its signature attraction, TILT, leans a group of visitors and the glass around them outward over Michigan Avenue for a genuine jolt of vertigo. A bar and cafe let you nurse a drink at altitude while the lake and the shoreline stretch away below.

Robie House, in the Hyde Park neighborhood beside the University of Chicago, is widely regarded as the finest expression of Frank Lloyd Wright's Prairie style and one of the most important houses in the history of architecture. Designed for businessman Frederick Robie, it distills Wright's belief that a building should grow from its site and reflect the flat horizon of the American Midwest.

Everything about it emphasizes the horizontal: the dramatically cantilevered roofs that seem to float, the long bands of art-glass windows, the Roman brick with its raked horizontal joints, and the sweeping lines that pull the eye across rather than up. Wright designed the house as a total work of art, from the open-flowing interior spaces to the leaded-glass windows, the furniture, and the light fixtures, integrating them into a single unified vision that influenced modern architecture worldwide.

After years under threat of demolition, the house was rescued and painstakingly restored, and it is now protected as part of a group of Wright buildings recognized on the UNESCO World Heritage List. Touring the interior reveals how radically Wright rethought the house: the hearth at the center, the compression and release of the spaces, the play of light through hundreds of pieces of patterned glass. It is a pilgrimage site for anyone who cares about design.