3 great architecture tours in Chicago to book


It’s the birthplace of the skyscraper and home to giants like the 1,451-foot Willis Tower, the third-tallest building in the United States, and the new 1,198-foot St. Regis Chicago, the tallest skyscraper. world’s skyscraper designed by a woman, but skyscrapers are just the tip of the iceberg when it comes to Chicago’s dazzling architectural scene. Windy City’s vast assortment of styles includes New, Neoclassical and Art Deco gems; Frank Lloyd Wright marvels; and more modernist buildings by Ludwig Mies van der Rohe than any other city in the world. In fact, you could fill days with stories about Chicago architecture. Better yet, opt for an expert-led deep dive with three tours focusing on the city’s most fascinating works.

Chicago’s “First Lady” River Cruises with the Chicago Architecture Center

  • Where and when: Cruises depart from the Chicago Riverwalk Pier near Michigan Avenue and Wacker Drive (112 E. Wacker Dr.) several times a day, seven days a week, from late March through mid-November.
  • Tour duration: 90 minutes
  • Price: From $52
  • To buy tickets: through the ACC website

For the best comprehensive tour of the city’s most impressive structural giants that doubles as a fun leisure cruise on the Chicago River, you can’t do better than the Chicago Architecture Center (CAC) River Cruises aboard Chicago’s First lady. These river cruises stand out from the others because they are carried out in partnership with the CAC and always supervised by the centre’s volunteer guides. Steve Haddad, an accomplished orthopedic surgeon by trade, is one such guide. “We’re lucky to have so many periods and building styles represented here, preserved like a time capsule from the Great Chicago Fire of 1871,” Haddad says. Seeing a handful of these styles nonstop is among the many perks of this cruise, along with the chance to explore all three branches of the Chicago River for breathtaking views of Chicago’s most iconic architecture from the vantage point. unique view of the water.

It’s one of the best ways to see Willis Tower, Trump Tower, and St. Regis Chicago, the latter of which Haddad praises for its striking contemporary style and intricate structural engineering components, including its layered glass. and its blown floor. The successes of this architectural cruise keep pouring in at every bend in the river: there are art deco gems like the sprawling Merchandise Mart and the history of the Tribune Tower with its cathedral roof, the Lyric Opera art nouveau that hovers just above the river like a canyon wall, the white terracotta Wrigley Building built by the chewing gum magnate of the same name, Harry Weese’s surprising nautical cottages at the foot of the street bridge Kinzie, the list goes on. You’ll be amazed by the cityscape, especially at the end of the cruise, when the boat turns around at the mouth of the river and Lake Michigan for panoramic views of the Chicago skyline.

Guided tours with the Frank Lloyd Wright Trust

  • Where and when: The Chicago Bus Tour departs from the lobby of the Rookery Building on Thursdays June through October, 9 a.m. to 4 p.m. Tickets sell out early, so book ahead. Tours of the Oak Park Home and Studio are offered daily between 10 a.m. and 4 p.m. at 951 Chicago Ave., Oak Park.
  • Tour duration: Seven hours for the Chicago tour; one hour and 45 minutes to visit Oak Park
  • Price: $195 for the Chicago tour (includes lunch and prosecco toast); $30 for Oak Park Tour
  • To buy tickets: through the Frank Lloyd Wright Trust website

For architecture enthusiasts, no trip to Chicago is complete without a visit to the masterpieces designed by the Midwestern native Frank Lloyd Wright. Best known for his unique American prairie-style homes, Wright’s style was perfected during his time in the nearby town Chicago neighborhood from Oak Park (about a 20-minute drive from town), home to more Wright homes than anywhere in the world. But the city is also home to a handful of Wright’s important works and interior compositions.

Check out the non-profit Frank Lloyd Wright Trust for a choice of expert-narrated tours, including our two favorites. For the ultimate sampling of all things FLW, the seasonal “Wright Around Chicago” takes you on an exclusive small-group bus tour to the architect’s most notable works across the city. Enter Rookery Light Court in the Financial District, one of Chicago’s first skyscrapers, and Wright’s home and studio in Oak Park, where more than 140 buildings were designed. After lunch at a local cafe, visit the Temple of Unity in Oak Park, a UNESCO World Heritage Site, before heading to the innovative Robie House in Chicago’s South End, considered one of of the most influential house designs of the early modern era. A scenic drive along the lake brings you back to the Rookery, where you end the tour with a toast of prosecco.

For those short on time and who love beautiful, nature-inspired homes, head to Oak Park for a combo home and studio tour with a self-guided walking tour. The tour is offered year-round and takes you inside the architect’s home and workplace, where the prairie style was born and where your guides explain how the two spaces served as experimental laboratories for Wright. Take the self-guided walking tour before or after the guided tour to discover the historic district rich in Wright influences.

Bronzeville tour with TikTok sensation Dilla

  • Where and when: Tours depart every other Saturday at 2:00 p.m. from the South Lot of the DuSable Museum of African American History (740 E. 56th Pl., Chicago).
  • Tour duration: Two o’clock
  • Price: $45
  • Book tickets: via the Chicago Mahogany website

“Everything dope about America comes from Chicago,” says Sherman “Dilla” Thomas, lifelong Chicago resident and local historian known for his 60-second TikTok videos about the city’s history. With a total of 150,000 followers across all social media, @6figga_dilla’s unique approach to sharing Chicago’s untold stories has also earned him a number of accolades, including 2022 Chicago Tourism Ambassador of the Year . Dilla is also currently working with Netflix on releasing a historical fiction series based on a true Chicago event.
Visitors to Chicago can experience the radical style of Dilla’s story telling live and right at the feet of important architectural works during his Chicago Mahogany Tours. Opt for the popular Bronzeville tour, which can accommodate up to 50 people by coach. Dilla leads the tour, so imagine the entertaining vibe of her TikTok videos, while sightseeing and hopping here and there to explore sights like the Eighth Infantry Armory – the first of its kind built for an African-American military regiment – the Supreme. Liberty Life Insurance Building, the Ida B. Wells-Barnett Mansion, and the Pilgrim Baptist Church, considered the birthplace of gospel music.


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