What to Include in the Chicago Architectural Tour: Chicago Itineraries 101

July 28, 2022
Liz Arnold

Among the many highlights of the Windy City, few are more iconic than its extraordinary wealth of architectural masterpieces. Chicago features one of the largest and most diverse collections of buildings designed by some of the most celebrated American architects, such as William Le Baron, Frank Lloyd Wright, Louis Sullivan, and Mies Van der Rohe, resulting in the iconic skyline we can admire today.

Architectural foundation tours are a must for any visitor. Besides, you can opt for Chicago group transportation, so the tour is pleasant and accessible to all your guests regardless of age and physical abilities. Here are some of the highlights of all Chicago architectural tours.

The Chicago Loop

Chicago’s business district is affectionately known as “The Loop”. It owes its moniker to the two cable car lines built in 1882 that shared a loop bounded by Van Buren Street, Wabash Avenue, Wells Street, and Lake Street. 

The Chicago Loop is home to some of the most famous Chicago landmarks and is a must in all Chicago itineraries. Some of the most notable buildings include the Chicago Board of Trade Building and the Willis Tower (formerly known as the Sears Tower), which was once the world’s tallest building. Since the most exciting structures are spread out, you may want to organize an architectural bus tour of Chicago.

Chicago Lakefront

All the best Chicago architecture tours will take time to explore the scenic Chicago lakefront. Facing the turquoise blue water of Lake Michigan, the lakefront area features stunning views of the Chicago skyline and is primarily used for recreational purposes. From multi-use trails and white sanded beaches to concert venues and welcoming parks, the lakefront district is an essential part of any Chicagoan’s life and visitors’ favorite stop. 

It features spectacular displays of outdoor sculptures created by the likes of Pablo Picasso, Joan Miró, Henry Moore, Marc Chagall, Magdalena Abakanowicz, and Alexander Calder, as well as Anish Kapoor’s iconic “Cloud Gate”, along with museums as breathtaking outside as they are inside.

Carbide and Carbon Building

Your guests may already have checked into the Carbide and Carbon Building since it was converted into the Hard Rock Hotel in 2004. Designed by the Burnham Brothers and built in 1929, it is a masterpiece of the Art Deco style and will not fail to wow your visitors on any Chicago building tours. According to the local legend, the architects pulled their inspiration from a Champagne bottle, using black granite with black marble and bronze trim as the exterior base, dark green and gold terra cotta as the central shaft, and an exquisite 24k gold-covered tapered cap.

The Rookery

All Chicago architectural tours should include a stop at this spectacular location, completed by architects Daniel Burnham and John Wellborn Root of Burnham and Root in 1888. In the wake of the Great Chicago fire of 1871, architects competed nationwide, mixing modern building techniques, such as fireproofing, elevators, and plate glass, together with Old-World-inspired aesthetics. 

The Rookery is a prime example of what is now known as the Chicago school of commercial architecture. In addition, revered architect Frank Lloyd Wright himself redesigned the sky-lit, two-story lobby in 1905, aptly known as the Light Court. This celebrated landmark has been part of the National Registry of Historic Places since 1970 and is now home to prestigious businesses and offices.

best chicago architecture tour

Chicago SkyDeck

If you have caught a glimpse of former Chicago visitors suspended into clear observation boxes offering vertiginous views of the city below on social media, you have already met guests of the Chicago SkyDeck. Displaying breathtaking panoramas spanning up to four states on a clear day, the Chicago Sky Desk stands 1,353 feet off the ground and is not for the faint of hearts. 

However, it is undoubtedly a highlight for any first-time or returning visitors and a must-have for the best Chicago architecture tour. Make sure you include this unique experience when designing Chicago itineraries for your guests.

Chicago Board of Trade

Until it was dethroned by the Richard J. Daley Center in 1967, the Chicago Board of Trade once stood as the tallest building in the Windy City since its inception in 1930. Erected at 44-story and 604 feet tall, this Art Deco behemoth features gray Indiana limestone and a massive, 31-feet statue of the Roman goddess of grain Ceres dominating it. It also displays impressive murals on the trading floor. It is an especially spectacular stop on Chicago architectural tours by night since its upwardly-lit floodlights further emphasize the structure's vertical elements.


Chicago has nothing to envy even for the most spectacular architecture tours in Europe. The Windy City features a unique and breathtaking display of examples of American entrepreneurial spirit and imagination in the form of vertiginous skyscrapers of all shapes. Hiring a Chicago charter bus company is the most comfortable and accessible way to explore this unique setting. If you are considering including an architectural bus tour of Chicago as part of the entertainment for your personal or business guests, do not hesitate to contact us for a personalized quote for your bus tour.

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