Explore Chicago’s groundbreaking architecture with our one-day itinerary that whisks your group from walking and boat tours to sky-high city views.

Chicago is known around the world for its amazing architecture, with a skyline shaped by some of the most important architects in history, including Frank Lloyd Wright, Mies van der Rohe and Daniel Burnham. See some of the city’s iconic design masterpieces and learn the fascinating stories behind them during this exciting one-day group itinerary filled with top Chicago architecture tours and attractions.

Lou Mitchell's

Fuel up for the day at Lou Mitchell’s, a favorite breakfast spot for locals and Route 66 travelers since 1923. The specialty of the house is fluffy jumbo omelets made with farm-fresh eggs and a huge selection of ingredients (try the version with sweet Michigan apples and Old English cheddar cheese) that are cooked and served in a skillet, sided with hash browns and toast meant to be slathered with Lou’s homemade orange marmalade. Other great Loop-area breakfast options include The Bongo Room and Eleven City Diner.

The Rookery Lobby

Head to the stunning new Chicago Architecture Center overlooking the Chicago River. The sprawling 20,000-square-foot space features impressive exhibits like the giant skyscraper models showcased in the dramatic Draper Family Skyscraper Gallery, featuring 40-foot-tall windows that overlook the Michigan Avenue Bridge. And don’t miss the Chicago Gallery, which illustrates how the city became the epicenter of modern architecture and features the interactive Chicago Model that shows Chicago’s growth from its earliest structures built after the Great Chicago Fire to today’s modernist marvels.

Join a tour led by the experts from the Chicago Architecture Center. With more than 85 tours, it may be hard to choose just one. But a sure bet is the Historic Skyscrapers downtown walking tour that explores some of the world’s earliest skyscrapers. Highlights of the two-hour Loop tour include the ornate Rookery building designed by Burnham (with an interior atrium redesigned by Wright), as well as Dankmar Adler and Louis Sullivan’s Auditorium Building. The Chicago Architecture Center organizes group tours with flexible departures and time frames, and all walking and bus tours include free admission to the Center, which is housed in a Mies van der Rohe building. 

If your group would like to delve further into the fascinating history of The Rookery, the Frank Lloyd Trust offers guided tours of The Rookery's lobby, central light court and Burnham Library. Groups tours are available.

Copy of Skydeck Chicago The Ledge

Next, step into an elevator and zoom up to the 103rdfloor Skydeck Chicago, where you’ll be greeted by jaw-dropping panoramic views thatcan span up to four states and nearly 50 miles on a clear day. A highlight is The Ledge, a hovering glass box that extends four feet out from the facade of the Willis Tower, creating an unforgettable viewing experience 1,353 feet above Chicago. Groups are hosted by the Skydeck Chicago Guest Relations staff, which can handle everything from arranging discount tickets for reservations of 20 or more to organizing group photos as souvenirs and special experiences like Breakfast on The Ledge.

©The Berghoff

Enjoy lunch at The Berghoff, which first opened its doors in Chicago in 1898. The Berghoff was originally established as a tavern by German immigrant Herman Joseph Berghoff to showcase his family’s beer. It eventually expanded into a full-service restaurant and has been run by family members ever since. The Berghoff proudly displays its Chicago Liquor License No. 1 behind its original historic bar, the first license issued after the end of Prohibition. The Berghoff has come full circle with the recent addition of a new on-site microbrewery that produces German-style beers. Order a frosty Berghoff beer, as well as classic German dishes like the wiener schnitzel sided with the restaurant’s famed creamed spinach and spätzle. The Berghoff offers several private and semi-private dining spaces for groups of all sizes. More good Loop lunch spots include Italian Village and Park Grill at Millennium Park.


Chicago's First Lady-2

Head to the award-winning Chicago Riverwalk (home to waterside cafes and attractions) and hop on the Chicago Architecture Center River Cruise Aboard Chicago’s First Lady Cruises. Voted the #1 tour in the U.S. by TripAdvisor, this popular 90-minute cruise is narrated by certified docents who point out more than 50 architectural gems along the three branches of the Chicago River. As you pass by you’ll hear about Chicago’s interesting history and the design giants who helped create the city’s world-famous skyline. Book reservations for groups of 10 or more; certain discounts may apply for groups of 20+. Excellent narrated architecture cruises are also offered by Wendella and Shoreline Sightseeing.

Copy of TILT at 360 CHICAGO - Romance

Afterwards, walk along the Magnificent Mile to 360 CHICAGO, a dazzling observation deck nestled on the 94th floor of the former John Hancock Center (now known as 875 North Michigan Avenue) that was cited as offering one of the Best Views in America by Travel + Leisure magazine. The tower is one of the tallest buildings in the city, and its distinctive X-shaped external bracing has made it a Chicago architecture icon. The highlight of a visit to 360 CHICAGO is TILT, a huge steel-and-glass bay window that is hydraulically tilted forward, giving visitors a heart-stopping downward-facing view of the city from 1,030 feet up in the sky. Discounted admission is offered for groups of 20 or more.

Punch Bowl Social Chicago

For dinner, why not try one of Chicago's hot new restaurants? The highly anticipated Pacific Standard Time recently opened in the River North neighborhood, helmed by acclaimed chef/co-owner Erling Wu-Bower who focuses on California-style fare ranging from swordfish to Asian-influenced ricotta dumplings. Punch Bowl Social opened its first Chicago location in the hip West Loop. The 30,000-sq.-ft. space offers private karaoke rooms, a bocce court, bowling, and arcade and virtual reality games. James Beard Award-winning chef Hugh Acheson is the brains behind the Southern-inspired menu. 


Open House Chicago

Open House Chicago, a free public festival hosted by the Chicago Architecture Center from October 13-14, 2018, features more than 250 architectural treasures and hidden gems that open their doors for self-guided tours. Structures located in 30 different neighborhoods range from soaring skyscrapers to opulent mansions and exclusive private clubs, many of which are rarely open to the public. No tickets or registration are required, and you can build your own group itinerary based on your must-sees.

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