Chicago’s Best Examples of Postmodern Architecture You Need to See

A New Chapter in Chicago’s Architectural Story

Chicago has always been a city that pushes architectural boundaries. It’s where the skyscraper was born, where steel first redefined what a city could look like, and where creativity continues to shape its skyline. After decades of glass-and-steel modernism, the late 20th century brought something new: postmodern architecture — a playful, sometimes ironic response to the strict, minimalist buildings that came before it.

This movement brought color, ornament, and personality back to the city’s skyline. Instead of rejecting history, postmodernism embraced it, mixing classic references with modern forms. In Chicago, it created buildings that are both intelligent and expressive, each telling a story about the evolution of design.

To fully appreciate these structures, there’s no better way than from the water. Aboard Tours & Boats’ 90-Minute Architecture Cruise, you’ll see many of Chicago’s postmodern landmarks from a fresh perspective — with expert narration that brings their history and artistry to life.

If you’re exploring the city or taking one of its famous architecture boat tours, these are the best postmodern architecture examples to keep an eye out for.

1. Harold Washington Library Center

At the corner of State and Van Buren, the Harold Washington Library is hard to miss. Designed by Hammond Beeby Rupert Ainge Architects, it opened in 1991 and quickly became a defining symbol of Chicago’s postmodern identity.

Its red brick facade recalls the grandeur of Chicago’s early civic buildings, while the large green roof ornaments — shaped like owls and foliage — add an almost whimsical touch. The combination of historical references and modern structure perfectly captures postmodernism’s spirit: confident, clever, and willing to stand out.

Inside, you’ll find a stunning glass-domed atrium and one of the most beautiful public library spaces in the country. Whether you’re an architecture enthusiast or just passing by, this building deserves a closer look.

2. James R. Thompson Center

Perhaps the most controversial of Chicago’s postmodern landmarks, the Thompson Center, designed by Helmut Jahn, opened in 1985 as the home of Illinois state offices. Its massive curved glass facade and open atrium were meant to represent transparency in government — a bold idea reflected in the building’s all-glass exterior.

While not everyone loves it, the Thompson Center remains one of the most important examples of famous postmodern architecture in Chicago. Its bold colors, exposed structure, and dramatic shape make it a striking statement of 1980s design thinking.

Today, with Google’s planned restoration of the building, it’s getting a second life — a modern take on a postmodern icon.

3. 333 Wacker Drive

Few buildings capture attention on the Chicago River quite like 333 Wacker Drive. Designed by Kohn Pedersen Fox and completed in 1983, this curved glass tower reflects the river’s green water and surrounding cityscape like a mirror.

The building is often cited in architecture tours for its unique way of harmonizing with its environment. Its soft curve contrasts beautifully with the city’s sharp, angular skyline. The blend of function and symbolism makes it a defining work of postmodern architecture in Chicago.

If you’re taking an architecture boat tour, this is one of the highlights — and seeing it from the river is the best way to appreciate how perfectly it fits into its surroundings.

4. The AT&T Corporate Center (now Franklin Center)

Standing tall at 37 stories, the AT&T Corporate Center (1989) combines Gothic revival details with modern skyscraper proportions. Designed by Adrian D. Smith of SOM, it uses granite cladding and spires that recall Chicago’s historical towers while maintaining a distinctly modern presence.

It’s another example of how postmodernism in Chicago drew inspiration from the past without simply copying it. Instead, it reinterpreted history through the lens of modern engineering and materials.

When viewed from a distance, especially near the river, the building’s crown and vertical lines make it one of the most distinctive silhouettes in the skyline.

5. NBC Tower

Completed in 1989 and designed by Skidmore, Owings & Merrill, the NBC Tower is a striking example of how postmodernism could merge corporate identity with visual flair. Its limestone cladding, tiered setbacks, and ornamental spire pay homage to the Art Deco style of the 1930s — particularly the Rockefeller Center in New York, which inspired it.

The building combines elegance with energy. During nighttime, its illuminated crown makes it one of the most recognizable sights along the riverfront. It’s a perfect stop for anyone exploring downtown’s architectural highlights.

6. Two Prudential Plaza

Right next to its mid-century neighbor, the original Prudential Building, stands Two Prudential Plaza, completed in 1990 and designed by Loebl Schlossman & Hackl. Its triangular top and offset setbacks create a dynamic form that nods to both modern and historical design.

What makes it special is how it complements Chicago’s skyline without repeating what’s already there. Postmodern architects loved to layer meaning and geometry, and this building demonstrates that beautifully.

From the water, its angular peak stands out clearly — especially on a sunny afternoon cruise.

Why Postmodern Architecture Matters in Chicago

Postmodernism marked an important shift in architectural thinking. After decades of uniform modernist boxes, it reintroduced individuality and creativity into design. In a city known for innovation, that mattered.

Chicago’s postmodern buildings symbolize freedom of expression in architecture. They celebrate both the city’s history and its constant reinvention. Whether you love or dislike their eccentric shapes, they remind us that architecture is an art form — one that evolves with time, culture, and technology.

See Chicago’s Postmodern Landmarks from the Water

While you can visit many of these buildings on foot, there’s no better way to see them than from the river. The Tours & Boats 90-Minute Architecture Cruise takes you through all three branches of the Chicago River, offering unbeatable views of the city’s most iconic and postmodern landmarks.

Tours & Boats also offers private cruises and group discounts, making it easy for architecture enthusiasts, schools, and companies to enjoy the skyline together. You can find details on their website to book your spot in advance, especially during peak seasons.

Chicago’s skyline is a living museum of design — from the birthplace of the skyscraper to today’s most creative structures. Take time to appreciate how each of these landmarks reflects a different chapter in Chicago’s architectural journey. And if you truly want to see how they interact with the city’s rhythm and light, hop aboard a river cruise with Tours & Boats — the view from the water reveals everything that makes this skyline unforgettable.