Chicago is known worldwide for its stunning architecture, boasting many famous buildings that define its skyline and history. In this guide, we highlight the top 5 famous buildings in Chicago that every visitor and local should know. Each landmark has a unique story, from record-breaking heights to architectural innovations. Whether you’re an architecture enthusiast or just exploring the Windy City, these iconic sites are a must-see. For local expertise and support, call Insure on the Spot in Chicago at 773-202-5060 for personalized service and advice.
1. Willis Tower (Sears Tower) – Chicago’s Tallest Skyscraper
Chicago’s most iconic skyscraper is Willis Tower, formerly known as the Sears Tower. Soaring 110 stories above downtown Chicago, it held the title of world’s tallest building for nearly 25 years after its completion in 1973. This gleaming black tower, designed in the International style, remains the tallest building in Chicago and offers breathtaking views of Illinois and beyond from its Skydeck observatory. Locals still fondly refer to it as the Sears Tower, a testament to its enduring presence in Chicago’s culture.
- Height: 1,451 feet (442 m) with 110 floors
- Location: Chicago’s Loop (233 S. Wacker Drive)
- Notable Feature: The Skydeck on the 103rd floor has glass-floored “Ledge” boxes where brave visitors can step out and look straight down at the city. Over a million tourists visit the Skydeck every year, making Willis Tower one of the most popular attractions in Chicago.
2. Tribune Tower – Neo-Gothic Landmark on Michigan Avenue
The Tribune Tower is a historic skyscraper known for its neo-Gothic architecture and storied past. Completed in 1925 as the home of the Chicago Tribune newspaper, this 36-floor tower stands proudly on North Michigan Avenue (the Magnificent Mile). It features ornate stone carvings, flying buttresses at its peak, and a crown that lights up at night. A unique detail is that its walls are embedded with fragments of famous structures from around the world – including pieces of the Great Wall of China and Notre Dame Cathedral – collected by Tribune reporters, adding to its global allure.
Chicagoans treasure Tribune Tower as a symbol of the city’s rich media and architectural history. Today, the building has been converted to luxury residences, but its grand facade remains a must-see. Standing across from the Wrigley Building by the Chicago River, Tribune Tower helps anchor the skyline with Old World elegance amidst modern high-rises.
3. The Rookery Building – Chicago’s Oldest High-Rise
Built in 1888, The Rookery Building is often cited as the oldest standing high-rise in Chicago. Located in the heart of the Loop’s financial district (at 209 S. LaSalle Street), this 12-story architectural gem combines historic charm with innovative design. The exterior blends Romanesque and Queen Anne styles, featuring red granite, intricate terra cotta ornaments, and sturdy brickwork that survived over a century. The name “Rookery” comes from an old City Hall that once occupied the site, which had become a roost for pigeons – a bit of Chicago trivia that stuck.
Inside, The Rookery boasts a stunning light court lobby redesigned by famed architect Frank Lloyd Wright in 1905. Sunlight pours through an elaborate glass ceiling onto white marble surfaces and an elegant central staircase, creating an airy oasis in the city’s hustle. As a Chicago Landmark, The Rookery is open for tours, allowing visitors to step back in time and appreciate early skyscraper engineering firsthand.
4. Marina City – The “Corn Cob” Towers of the Chicago River
Nothing captures Chicago’s 1960s urban creativity quite like Marina City. Completed in the mid-1960s, this mixed-use complex on the north bank of the Chicago River features two cylindrical towers that locals affectionately call the “corn cob” buildings. Each tower rises 65 stories and was among the tallest residential structures of its time. Architect Bertrand Goldberg’s unique design eschewed traditional boxy forms for graceful curves, symbolizing a bold new approach to city living in Illinois.
Marina City’s towers house apartments on the upper floors with open-air balconies forming the corn cob pattern, while the lower levels contain spiraling parking garages visible from outside. The complex originally included restaurants, a theater, a bowling alley, and even a marina at river level – a city within a city. This forward-thinking design helped revitalize downtown living. Marina City is also famous in pop culture, appearing in TV shows, album covers, and an iconic scene where a car was driven off the parking deck for a movie stunt. Even today, these landmark towers remain a striking and photogenic part of the Chicago skyline.
5. Wrigley Building – Historic Beacon on the Magnificent Mile
The Wrigley Building is a beloved Chicago landmark that gleams with sophistication. Opened in 1924 as the headquarters of the Wrigley chewing gum company, it consists of two connected towers on Michigan Avenue right next to the Chicago River. The design was inspired by Spanish Colonial Revival architecture, including elements modeled after the cathedral tower in Seville, Spain. Clad in glossy white terra cotta tiles, the Wrigley Building’s facade is brightly illuminated at night, earning it a reputation as the “shining white castle” of the Magnificent Mile.
- Location: 400–410 N. Michigan Avenue (Near North Side)
- Height: South Tower 425 feet (30 stories), North Tower 21 stories
- Key Features: A large clock face adorns the south tower, and the building was Chicago’s first air-conditioned office building. It’s also noted for its beautiful plaza and walkway that provide a scenic view of the Chicago River. Designated as a Chicago Landmark in 2012, the Wrigley Building remains an enduring symbol of the city’s architectural innovation and commercial success.
To summarize, here’s a quick comparison of these five famous Chicago buildings:
| Building | Year Completed | Height | Known For |
| Willis Tower | 1973 | 1,451 ft (110 floors) | Tallest in Chicago; Skydeck observatory with glass ledge |
| Tribune Tower | 1925 | 463 ft (36 floors) | Neo-Gothic design; stones from world landmarks in walls |
| The Rookery | 1888 | 181 ft (12 floors) | Oldest standing high-rise in Chicago; Frank Lloyd Wright-designed lobby |
| Marina City | 1964–1967 | 587 ft (65 floors each) | Twin “corn cob” towers; mid-century urban mixed-use design |
| Wrigley Building | 1924 | 425 ft (30-story south tower) | Iconic white terra cotta facade; first air-conditioned office in Chicago |
Frequently Asked Questions (FAQs)
Q: What is the tallest building in Chicago?
A: The tallest building in Chicago is Willis Tower, standing at 1,451 feet. It has 110 stories and offers panoramic city views from its Skydeck observation deck.
Q: Why is Chicago known as the birthplace of the skyscraper?
A: Chicago is called the birthplace of the skyscraper because it was home to some of the first steel-frame high-rises in the late 19th century. The city’s innovative architectural history includes the 1885 Home Insurance Building, considered the world’s first modern skyscraper.
Q: Can you visit these famous Chicago buildings?
A: Yes, several famous buildings are open to visitors. For example, Willis Tower has the Skydeck for tourists, and guided tours are available for historic sites like The Rookery. Even buildings not fully open to the public can often be admired from nearby plazas or lobbies.
Q: What are the “corn cob” buildings in downtown Chicago?
A: The “corn cob” buildings refer to Marina City, a pair of round, 65-story towers on the Chicago River. Their unique scalloped design resembles corn cobs, making them one of the city’s most recognizable architectural feats from the 1960s.
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