Chicago is an outstanding city often known for its deep dish pizza, invention of the chocolate brownie, vibrant jazz scene and unwavering support of its sports teams, but not many visitors know that 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.
2025 will see the 140th anniversary of this incredible architectural concept, and there is still no better city to explore the development of architecture throughout history. Chicago has many ways to do this from the water, its streets, or from up above within some of the city’s fascinating buildings.
Chicago Architecture Center River Cruise
Known as one of the most popular tours in the US, the Chicago Architecture Center River Cruise offers guests a spectacular journey along the Chicago River. During this fantastic 90 minute tour, architectural experts share stories of more than 50 iconic buildings and the legendary figures who designed and built the city. Aboard Chicago’s First Lady, guests enjoy unobstructed views from the open-air upper decks. The experience allows them to appreciate the city’s history while sipping on cocktails or hot beverages, leaving them educated and excited to explore the city.
To find out more, visit 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 world-renowned architecture.
Guests will 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, allowing them to fully immerse themselves in the rich history of Chicago.
To find out more, visit insidechicagowalkingtours.com
The Obama Presidential Center *NEW FOR 2026*
Covering 19 acres, the campus will include a fruit and vegetable garden, an athletic facility for programs and events, a premier museum, an auditorium, a branch of the Chicago Public Library, and additional amenities. The programming will encourage visitors, whether local or international, to carry the impact of their experience with them. The museum, which will be a historic landmark in Jackson Park, will be a four-sided building, inspired by four hands coming together, with the architectural design echoing the movement of grassroots upwards, and each side providing a unique view. 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.
How: For more information, visit www.obama.org/presidential-center
Frank Lloyd Wright’s Robie House
Chicago is home to many of world renowned architect Frank Lloyd Wright’s buildings, including the iconic Robie House, constructed in 1910. Located in Chicago’s Hyde Park neighbourhood, Robie House is considered one of Wright’s stand out designs for his signature Prairie style with its strong horizontal lines, and as well as being known as one of the most important buildings in the 20th century, 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 of this incredible building.
For more information, visit 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.
To find out more please visit architecture.org
Architecture of the Magnificent Mile
Guests on this exceptional 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., ensuring a perfect day out.
To find out more please visit 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 the endless amount of architectural history that Chicago has to offer. A non-profit organisation that helps to inspire people to discover why design matters, there is a tour that suits every visitor. It’s also home to a selection of engaging and interactive exhibitions such as the Chicago City Model Experience, Framed Views, and Disruptors for visitors to enjoy.
HOW: To find out more about the Chicago Architecture Centre please visit architecture.org
