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Chicago Architecture: 7 Iconic and Groundbreaking Structures

August 16, 2022 By CityPASS

Although the Windy City is home to some of the most impassioned sports fans and delicious pizza this nation offers, it's also home to many of the most emblematic and groundbreaking architectural displays in the United States — but it wasn't always that way.

Maybe you've heard of the famous Chicago Fire of 1871, but what you might not know is that rumor has it the fire started when a cow knocked over a lantern and caused three miles of fiery evisceration to Chicago's all-wooden downtown. This event, while terrifying and tragic, forced Chicago to rethink its urban planning methods and building materials, and changed how it could utilize all of the real estate in the city, including in its sky.

The Chicago architecture and skyline transformed after the 1871 fire, and the years afterward became known as the age of skyscrapers — with many buildings being built that were recognized at the time as the tallest buildings in the world. Today, South Wacker Drive is home to many of these industrial giants, including a post-modern, 65-foot skyscraper that is currently the 9th tallest building in the city. With an architecture tour in Chicago, you're guaranteed to see some of the most historic spaces in the city.


A Walk Through Chicago Architecture and Design: Tallest and Most Historic Buildings

As more skyscrapers were built and more brilliant engineering minds brought their creativity and innovation to Chicago, the architecture and design style of the city became a melting pot of influences and styles. While the city grew rapidly in the early and mid-1900s, so did the buildings — and many of them still stand today as historic representations of the same resilience and strength Chicago is known for. Among the many architectural styles found in the city, Chicago is home to the famed International and Prairie School style.

1. John Hancock Center

A true Chicago landmark and an iconic example of late 20th-century Chicago architecture, 875 N. Michigan Ave has come to symbolize the expressiveness of structure within the city. On the 95th floor, you'll find The Signature Room, a fine dining restaurant with incredible views of Lake Michigan and the city skyline — nearly 1000 feet above the water. On the 94th floor you can also experience amazing views of the city at 360 CHICAGO Observation Deck. John Hancock Center is currently the fifth-tallest building in the city and the 13th-tallest in the United States, standing at 1500 feet when measured up to its antenna masts.

2. Monadnock Building

This 16-story skyscraper is located on Jackson Boulevard in the South Loop of Chicago and holds the title of the tallest load-bearing brick building ever constructed. Remodeled in 1938 in one of the most comprehensive and groundbreaking renovations ever taken, the project to restore the Monadnock was recognized as one of the most celebrated in the US by the National Trust for Historic Preservation in 1987.


3. Rookery Building

Located in Chicago's downtown Financial District, The Rookery is easily recognized as a Chicago landmark and is on the National Register of Historic Places. Beloved and revered architect Frank Lloyd Wright redesigned the lobby in his signature Prairie style, making it the only building he worked on throughout the entire cityscape — except for one other as an apprentice at the architecture firm of Joseph Lyman Silsbee. At 181 feet and 12 stories tall, it is still considered the oldest standing high rise in the city of Chicago — and with its limestone exterior, it’s considered one of the most beautiful.

4. Tribune Tower

Directly across the street from the Wrigley building stands this Gothic Revival building, flush with Art Deco inspiration and taking crown notes from the Rouen Cathedral in France. The Chicago Architecture Center notes that "carved into the lobby walls are famous quotations from Benjamin Franklin, Voltaire, Thomas Jefferson, and James Madison, praising and exalting freedom of the press." Look for these as you admire the structural wonder of this house of truth.

5. Auditorium Building

On the corner of Ida B. Wells Drive and South Michigan, this design by Louis Sullivan and Dankmar Adler was completed in 1889 and has been part of Roosevelt University since 1947. President Grover Cleveland actually laid the cornerstone for the multi-use Auditorium Building, solidifying its place on the National Register of Historic Places in 1970. Another fun fact? The building was equipped with the first central air conditioning system and the theater was the first to be entirely lit by incandescent light bulbs.


6. Chicago Federal Center

Chicago Federal Center, designed by Ludwig Miles van der Rohe, emanates the adage "less is more." Simplified, modern, and efficient, the steel and glass buildings signified a new era in the form and function of public architecture. Perhaps the most interesting thing about this building is the fact that it was constructed on a rigid grid system — meaning that every column, fixture, bench, etc. — lines up on the grid. This beacon of efficiency and style reflects integrity on the inside just as much as it does on the outside.

7. Chicago Cultural Center

As an integral part of Millennium Park Campus, this gorgeous building — also known as the "People's Palace" — drew on Greek, Roman, and Italian Renaissance architectural structures to become the nation's first free municipal cultural center. It was the first permanent home for the Chicago Public Library before being re-established as the Chicago Cultural Center in 1991.


Enjoy a Chicago Architecture Boat Tour and the Beautiful City Skyline

For all of its expansiveness and architectural grandeur, Chicago is not always the most pedestrian-friendly city — so what better way to enjoy the beautiful skyline than on the Shoreline Sightseeing Architecture River Tour? Bask in the soft light of sunset or the radiant rays of the afternoon sun as you enjoy this architecture boat tour in Chicago that is sure to enlighten and astound you.

Making the most of your time in a city like Chicago is important because there's just so much to see and do, and planning days efficiently is key to fully enjoying your trip. When you purchase Chicago C3 tickets, you get admission to your choice of three top Chicago attractions, including the Shoreline Sightseeing Architecture River Tour. With Chicago C3, you can see the best the city has to offer without spending valuable time researching activities or seeking out multiple tickets — maximizing your ability to relax, take it all in, and enjoy.

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