On virtually any street corner in Chicago, you’re surrounded by the inspiration of world-renowned architects playing out in brick, cement, glass and steel. The city’s skyline reflects more than a century of architectural exploration sparked—in part—by the Great Fire of 1871, which decimated hundreds of old wood-frame and brick buildings squatting on the lakefront. In their place came a new generation of structures with steel skeletons perfected by the original Chicago School of architects: visionaries such as Louis Sullivan, Daniel Burnham and Dankmar Adler.
After WWII, a second Chicago School pressed even higher. Bruce Graham and Fazlur Rahman Khan’s Sears Tower (now called the Willis Tower) topped the skyline as the world’s tallest building in 1973. Their John Hancock Center, as well as Edward Durell Stone’s Aon Center and Ludwig Mies van der Rohe’s Lake Shore Drive Apartments, added to the portfolio of downtown scene-stealers.
Today, the Windy City is known worldwide for its collection of towering skyscrapers. Visitors explore the city’s built environment with tours by foot, water, bike, bus, trolley or train. Stops include imposing, spare modernist towers reflected in the flat expanse of Lake Michigan and older, smaller buildings packed with history. New buildings on the drawing board or in construction promise exciting new explorations.
In downtown Chicago, some buildings let you see for miles in every direction, while others let you peer directly into the past. The Chicago Cultural Center, for instance, looks all the way back to its 1897 opening as the Chicago Public Library, wowing visitors with a columned classical design of arched portals, multicolored marble and stained-glass domes topping symmetrical wings. Vaulting skyward, in contrast, is the 110-story Willis Tower, where visitors thrill to the views from The Ledge at Skydeck Chicago, where clear-glass cases jut out from the building’s 103rd floor.
The 1930 Merchandise Mart building is vast enough that it once earned its own ZIP code. Originally comprised of warehouses and showrooms for Marshall Field and Company, the building (now home to retailers and offices) shows off its Art Deco aesthetics with chamfer angles and a terrazzo-floor lobby with a 17-mural frieze.
With more than 70 buildings that top 500 feet, Chicago boasts one of the most impressive skylines on the planet.
As downtown boomed, architect Frank Lloyd Wright found a way to make the horizontal take wing in his Prairie School homes, all accented by geometric details and custom furniture. Oak Park showcases some of the best examples of this style, including the master’s own Oak Park Home and Studio starring a two-story children’s playroom with vaulted ceilings and a skylight. Take a one-hour guided tour, or if you have a few hours, combine it with a self-guided audio tour of the exteriors of seven Wright-designed homes in town. The annual Wright Plus Housewalk (May 20 this year) includes rarely offered interior tours of homes and buildings designed by Wright and his contemporaries.
Aside from the downtown area gutted by fire in 1871, perhaps no Chicago neighborhood has changed more than Pilsen on the southwest side. Once the home of Bohemian, Czech and German immigrants, the neighborhood has become a close-knit Mexican- American community. Many Old Europe-style buildings are adorned with modern murals. The 1892 Romanesque Revival Thalia Hall demands a visit, restored to imposing glory with its entryway of carved Bedford limestone beneath a vivid stained-glass window. The National Museum of Mexican Art offers a look at boldly colored pieces mirroring the neighborhood’s lively character.
Just northwest of the Loop, Beer Baron Row features lavish mansions built by wealthy businessmen around the turn of the 20th century. Those men likely gathered at the terra-cotta-fish-decorated North Avenue Bathes, now occupied by Trenchermen, a trendy gastropub. Still following its original role is St. Stanislaus Kostka Church in an elaborate Renaissance Revival-style building. Frescoes by Thaddeus Zukotynski cover the dome above the altar. On a lighter note, the Hermann Weinhardt House captures passersby with its gingerbread ornamentation and Christmasy color palette of green limestone and red brick.
Gothic architecture finds new and old forms on this wooded south-side Chicago school, with the ivy-covered Hull Gate and Joseph Bond Chapel well-suited for the grounds of European cathedrals. You’ll feel as if you’ve entered the Great Hall of Hogwarts while strolling through the William Rainey Harper Memorial Library, with its soaring arched ceiling and hulking chandelier. The more intimate Ida Noyes Hall charms visitors with intricately carved oak wainscoting and wrought-iron railings. Meanwhile, the blocky Henry Hinds Laboratory for Geophysical Sciences takes a modern twist on Gothic with an abundance of right angles.
Numerous companies offer kayaking tours on the Chicago River downtown, including Wateriders, Urban Kayaks and Kayak Chicago.
The Chicago Architecture Foundation helms a variety of tours throughout the city. The popular River Cruise aboard Chicago’s First Lady departs from downtown Chicago’s Riverwalk. Guides give insights into more than 50 buildings while sharing fun facts about the city’s history on 90-minute boat tours. Dozens of walking tours are themed around niche interests such as Tiff any Treasures and Evolution of the Skyscraper. For an all-encompassing view of the city on a tight timeline, opt for the Must-See Chicago tour, which involves hopping on and off the famous L train to see landmarks, such as the Wrigley Building, the Art Institute of Chicago and the Chicago Theater, all within a 90-minute time frame.
Come back in the autumn to experience the Chicago Architecture Foundation’s popular Open House Chicago event (October 14–15 this year), which allows free access to a changing menu of more than 200 architectural gems. Visitors will have exclusive access to skyscrapers, offices, private clubs, historic landmarks and some of Chicago’s most fascinating locales.
Chicago is far from done with architectural trendsetting. One example: the sleek, ribbon-like 93- story Vista Tower, slated to be finished by 2020. Several other new structures have commanded attention over the past few years:
• A mixed-use tower called Aqua has drawn stares and selfies since 2009 for its wavy 82-story configuration.
• The 60-story Waldorf Astoria Chicago—with a Parisian-style exterior complete with spires and colonnades—opened in 2010.
• OneEleven, a geometrically segmented glass tower housing luxury apartments, opened in 2014.
• The lakefront’s Navy Pier got a brand-new Centennial Wheel in 2016. Around 400 people can ride the 200-foot-tall wheel at a time. Gondolas feature interactive video screens loaded with Navy Pier information.
An hour’s drive northwest of Chicago, Woodstock’s town square is anchored by the ornate Woodstock Opera House, built in 1889 of local materials, including brick, fieldstone, terra-cotta and limestone, artfully combined in a structure showing various styles: Gothic, Victorian and Midwestern. Nineteenth-century storefronts (including the 1857 courthouse and sheriff ’s residence) surround a downtown park with a gazebo replicating one that originally sheltered a spring thought to have medicinal properties.
With a whopping 3,600 buildings on the National Register of Historic Places, this mid-state Mississippi River town stars endless examples of Federal Style and Greek Revival structures dating to the 1800s. Check out the Gothic Revival St. Francis Catholic Church, the Newcomb-Stillwell Mansion (doing duty as the Quincy Museum), Dick Brothers Brewery (now a fine arts gallery) and Villa Kathrine Castle, serving as the Quincy Visitors Center on a bluff above the Mississippi River.
Antique homes headline the sights in Galena, tucked into the state’s northwest corner. An impressive 85 percent of the town’s buildings are listed on the National Register of Historic Places, which includes such highlights as the Ulysses S. Grant and Elihu B. Washburne homes. Roughly following the Galena River, Main Street contains elaborate Victorian structures housing coffee shops, tearooms, boutiques, galleries, bed-and-breakfasts (there are 31 in town) and restaurants. On surrounding river bluffs, broad, shaded lawns surround the mansions built by steamship captains and owners of nearby lead mines, many ornamented with turrets, columns, ornate bay windows and all the other frills and flounces beloved by 19th-century homeowners.
Frank Lloyd Wright built many homes near his longtime residence in Oak Park. Wri...