Exploring Chicago's Skyline Through 28 Iconic Buildings

The Genesis of Skyscrapers

The skyline of Chicago hasn't always been adorned with shimmering skyscrapers. In 1871, a massive fire devastated much of the city, forcing about a third of its population to flee their homes. Though a catastrophe, this fire led to advancements in building materials and safety regulations, paving the way for the era of high-rise buildings.

The current landscape of Chicago reflects over a century of changes in architectural styles, building materials, and building heights. From any vantage point, the Chicago skyline is impressive, but to truly appreciate its beauty, you should view it from Lake Michigan. An architectural cruise on the Chicago First Lady or a Wendella boat about an hour before sunset will give you the chance to witness the sky transform into shades of pink and orange behind the city's silhouette before returning along the Chicago River.

North Chicago Views

This section includes the northern edge of downtown, where the sky meets Lake Michigan. Here, you'll find some of the most recognizable buildings along Michigan Avenue and the riverfront.

Lake Point Tower
Address: 505 N. Lake Shore Dr.
Floors: 70
Height: 645 feet

Lake Point Tower is famous for its colored glass framed in gold metal, with sunlight reflecting off Lake Michigan to create a stunning effect. Its curved shape is said to have inspired the Chicago designer of the Burj Khalifa, the tallest building in the world. The top floor of Lake Point Tower houses the Cité restaurant, where you can enjoy panoramic views of the city and beautiful sunset dinners.

Newer Structures

400 Lake Shore
Address: 400 N. Lake Shore Dr.
Floors: Under construction
Height: 858 feet

400 Lake Shore is one of the most striking additions to Chicago's skyline, replacing a long-vacant area previously occupied by the Chicago Spire. This project brings vibrancy to the area with two towers, the northern one soaring approximately 858 feet.

AMA Plaza
Address: 330 N. Wabash Ave.
Floors: 52
Height: 695 feet

This plaza sits along the Chicago River and features the Langham, a luxury hotel with two renowned restaurants you shouldn't miss. One offers high-quality American cuisine for breakfast, lunch, and dinner, while the other is famous for its “Langham Afternoon Tea.”

Trump International Hotel & Tower

Address: 401 N Wabash Ave.
Floors: 98
Height: 1,388 feet

Initially intended to be the tallest building in the world, Trump Tower was scaled down after the events of September 11. Situated along the Chicago River, the tower features a hotel and residences, offering stunning views of the riverside buildings.

875 North Michigan Avenue
Address: 875 N. Michigan Ave.
Floors: 100
Height: 1,128 feet

Also known as the John Hancock Center, this building boasts one of Chicago's two observation decks, where you can enjoy breathtaking views from the 94th floor.

Downtown

This area is the busiest part of Chicago's skyline, home to the tallest towers and famous historic landmarks. Many of Chicago's most iconic attractions are scattered within a few blocks in this region.

Aon Center
Address: 200 E. Randolph St.
Floors: 83
Height: 1,136 feet

The Aon Center, one of Chicago's tallest buildings, stands out with its simple rectangular design clad in white granite. Completed in 1973, the building underwent a major renovation to restore its original beauty after some stones had cracked.

The soaring height of the Aon Center makes it a prominent feature of the skyline next to Millennium Park.

Two Prudential Plaza
Address: 180 N. Stetson Ave.
Floors: 58
Height: 995 feet

The two Prudential towers are one of the city's symbols, blending modern design with Chicago's cultural history.