The Iconic Chicago Buildings Everyone Should See
Discover the awe-inspiring skyline that defines the Windy City, from historic gems to groundbreaking skyscrapers.
Chicago isn’t just known for deep-dish pizza and blues music, it’s one of the most architecturally significant cities in the world. From towering steel giants to century-old cultural treasures, the city’s skyline tells a fascinating story of innovation, resilience, and artistic vision. In this guide, we’re exploring the iconic Chicago buildings everyone should see at least once in their lifetime.
Whether you’re strolling the streets or floating down the river, there’s no better way to take in the Chicago famous architecture than by immersing yourself in its surroundings. And yes, we’ll talk about the best ways to do that, including the city’s top-rated architecture boat tour.
1. Willis Tower (Formerly Sears Tower)
No list of Chicago iconic buildings would be complete without the Willis Tower. Once the tallest building in the world, this 110-story skyscraper remains one of the most recognizable landmarks in the city. The Skydeck on the 103rd floor offers panoramic views, and the Ledge—a glass box extending four feet out—gives thrill-seekers a clear look straight down to the streets below.
2. The Wrigley Building
This white terra-cotta beauty on Michigan Avenue is one of the city’s most beloved architectural gems. Built in the 1920s as the headquarters for the Wrigley Company, it blends French Renaissance and Spanish Revival styles with a distinctive clock tower that lights up the Magnificent Mile. The building’s reflection in the river is especially breathtaking at night.
3. Tribune Tower
Just across from the Wrigley Building sits the historic Tribune Tower. Completed in 1925, it was the result of an international design competition that captured the world’s attention. The neo-Gothic structure is adorned with fragments from world landmarks—including the Great Wall of China and the Parthenon—embedded in its lower-level walls. A true nod to global history.
4. 875 North Michigan Avenue (Formerly John Hancock Center)
Known for its X-braced exterior, this sleek black tower is a masterpiece of structural expressionism. Visitors can take in city and lake views from the 360 CHICAGO Observation Deck, which offers a unique TILT experience, where the windows tilt outward for a thrilling downward view.
5. Marina City
Nicknamed the “corn cob” buildings, Marina City’s twin towers were designed by Bertrand Goldberg and completed in the 1960s. Their unique cylindrical design breaks the mold of traditional rectangular skyscrapers and helped reshape how people viewed urban living. The base houses a marina, restaurants, and a concert venue, making it an early example of mixed-use development.
6. Aqua Tower
One of the newer additions to Chicago’s skyline, Aqua Tower is a modern architectural wonder. Designed by Jeanne Gang, it features undulating balconies that create a flowing, ripple-like effect.
It’s not just a beautiful building, it’s a symbol of famous architecture in Chicago continuing to evolve.
7. Chicago Cultural Center
This lesser-known treasure is home to the world’s largest Tiffany stained glass dome. Originally the city’s first public library, this Beaux-Arts building now hosts art exhibitions, concerts, and public events. Its interior is nothing short of jaw-dropping.
8. The Rookery Building
Designed by Burnham and Root, with later renovations by Frank Lloyd Wright, the Rookery Building is a hybrid of iron framing and elegant ornamentation. The light-filled lobby with its intricate detailing remains one of the most admired spaces in the city.
9. The Chicago Board of Trade Building
An Art Deco icon, this building has stood as the heart of the city’s financial district since 1930. Its tiered silhouette and rooftop statue of Ceres (the Roman goddess of agriculture) make it a striking fixture on LaSalle Street. This is Chicago famous architecture at its boldest.
10. The Monadnock Building
A symbol of the city’s architectural transition from load-bearing walls to steel-frame construction, the Monadnock Building is a study in contrast. The northern half is brick masonry and the southern half steel-framed, showcasing two eras of construction within the same structure. It’s a must-visit for architecture buffs.
The Best Way to See It All: Chicago’s Best 90-Minute Architecture Boat Tour
Let’s be honest: walking the city is great, but nothing compares to seeing these iconic Chicago buildings from the water. The 90-minute architecture boat tour by Tours & Boats gives you front-row views of more than 40 architectural masterpieces while cruising along all three branches of the Chicago River.
This isn’t just another sightseeing ride. Tours & Boats offers:
- Expert guides who share fascinating historical and design context
- A fully enclosed, climate-controlled lower deck and 360° open-air upper deck
- Onboard restrooms, snacks, and a full bar
- Convenient parking and a centrally located dock
Rated one of the best Chicago tours, this is the most comprehensive architecture cruise available. You’ll not only cover all the landmarks we’ve listed, but also hidden gems you wouldn’t discover on your own.
Learn more or book your ticket here.
Why Architecture Matters in Chicago
Chicago’s buildings aren’t just beautiful, they also represent a resilient and visionary spirit. After the Great Fire of 1871, the city reinvented itself through bold urban planning and architectural experimentation. It became the birthplace of the skyscraper and a proving ground for countless innovations in engineering and design.
This legacy continues today, as the city balances preservation with new development. From Art Deco to contemporary eco-design, the architectural landscape in Chicago is always pushing boundaries.
From towering steel icons to elegant historic structures, the Chicago iconic buildings featured in this guide are more than just photo ops, they’re also part of a living, breathing cityscape. Whether you’re a first-time visitor or a lifelong resident, taking time to appreciate the famous architecture in Chicago will deepen your connection to the city.
And if you’re wondering which Chicago architecture boat tour is best, there’s no doubt: Tours & Boats combines depth, comfort, and coverage in one unforgettable experience. So next time you’re exploring the Windy City, don’t just look up, book a tour and see it all from the water.