How to explore Chicago’s architecture history

A little-known fact about Chicago: It was home of the first world’s first skyscraper.

In 1885, architect William Le Baron Jenney completed Chicago’s Home Insurance Building.

The building rose to an impressive height of 10 storeys, and while it is no longer standing, it changed the way in which cities were designed for years to come.

Next year will see the 140th anniversary of the birth of this architectural concept.

Chicago has many ways to appreciate its iconic buildings and architectural styles – from the water, looking up from the streets, or high above the famous skyline.

Chicago Architecture Center River Cruise

Known as one of the most popular tours, the Chicago Architecture Center River Cruise offers the perfect viewpoint from the Chicago River. During this Chicago tour, architecture experts share stories of more than 50 iconic buildings and the figures who designed and built the city. Aboard Chicago’s First Lady, guests enjoy unobstructed views from the open-air upper decks. www.architecture.org

Marvels & Masterpieces: An Engineer’s Guide to Chicago Architecture

Experience Chicago’s only engineering-themed walking tour, which takes visitors on a unique route that explores the engineering perspective behind the city’s architecture. Discover over 150 years of engineering advancements from a knowledgeable engineer who shares the stories and history of Chicago. Learn how some buildings gained a reputation for being haunted simply due to their uneven settling on floating foundations. In addition to understanding how the city’s iconic structures endure the test of time and withstand the forces of gravity and wind, visitors will have the opportunity to explore the interiors of select buildings.  www.insidechicagowalkingtours.com

The Obama Presidential Center (from 2026)

Covering 19 acres, the campus will include a fruit and vegetable garden, an athletic facility for programs and events, a museum, an auditorium, a branch of the Chicago Public Library, and other amenities. The museum, which will be a historic landmark in Jackson Park, will be a four-sided building, inspired by four hands coming together. The exterior will feature words from former President Obama’s speech that marked the 50th anniversary of the Selma to Montgomery marches. The multi-purpose athletics and event facility and campus at the Obama Presidential Center is set to open in 2026.   www.obama.org/presidential-center

Frank Lloyd Wright’s Robie House

Chicago is home to many of renowned architect Frank Lloyd Wright’s buildings, including the iconic Robie House, constructed in 1910. Located in Chicago’s Hyde Park neighborhood, Robie House is considered one of Wright’s stand out designs for his signature Prairie style with its strong horizontal lines. Robie house was named a UNESCO World Heritage Site in 2019. A variety of tours are available at Robie House that differ in length depending how much visitors want to dive into the history, design and cultural significance. www.flwright.org

Elevated Architecture: Downtown ‘L’ Train

One of the most popular ways to travel around Chicago is by the L train, also known as the elevated train. These trains take passengers across the city while operating approximately 20 feet above the ground. The Chicago Architecture Center offers a fantastic tour that allows visitors to explore the stunning architecture of Chicago from the unique perspective of elevated trains and platforms. This vantage point reveals architectural details often missed by those walking at street level. Led by knowledgeable and professional tour guides, guests will learn about the history of the famous ‘L’ system and gain a deeper understanding of how it has influenced the development of buildings in and around the Loop.  www.architecture.org

Architecture of the Magnificent Mile

Guests on this walking tour have the chance to explore Chicago’s transformation from a dirt road known as Pine Street to the iconic Magnificent Mile (Michigan Avenue), the city’s premier shopping district. This area boasts buildings inspired by a variety of architectural styles, including Parisian, Gothic, neoclassical, and Art Deco. The Magnificent Mile serves as a history book, showcasing signature architectural designs that have gained popularity over the years. Visitors will have the opportunity to view skyscrapers, vertical malls, residential towers, and buildings crafted to reflect the brands they house. Experienced tour guides will reveal the stories and secrets behind the fascinating structures on North Michigan Avenue. www.architecture.org

Chicago Architecture Centre

The Chicago Architecture Centre (CAC) is one of the best places to head to when looking for tips, ideas, and tours on how to explore architectural history.. It’s also home to a selection of engaging and interactive exhibitions such as the Chicago City Model Experience, Framed Views, and Disruptors. 

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