2024 Chicago Skyline: 9 Iconic Chicago Buildings and How to Explore Them

Thanks in part to its location on the western shores of Lake Michigan, Chicago grew from a small trading outpost to America's 3rd-largest city. Nearly all major rail transportation networks in the United States converge in Chicago, making the city arguably the nation's industrial crossroads. When Chicago rapidly expanded during World War I and in the decades that followed, the amazing skyline we know today began to take shape. Here are 9 iconic buildings that contribute to making Chicago such a great place for urban architecture.

We start at the top…literally. If you're from Chicago or were born before say 1995, you probably still call this Sears Tower. Constructed in 1974, it was the world's tallest building until 1998. Today, it remains the 3rd-tallest in the Western Hemisphere. Willis Tower's iconic black glass and steal exterior and twin white spires are instantly recognizable. Engineer Fazulr Rahman Khan pioneered the use of a tubular construction technique. To an observer, Willis Tower looks like several separate buildings all fitted together. This design allowed Rahman to build what was the world's tallest building in a city known for its ferocious winds. Visitors to the Willis Tower Skydeck on the 103rd floor are treated to views extending as far as Michigan and Wisconsin on clear days. Since 2009, the Skydeck has also featured a number of glass-bottom balconies that allow you to feel as if you're stepping out into thin air. It's a hair-raising experience that visitors to Chicago won’t want to miss!

[Address] 233 S Wacker Dr, Chicago, IL 60606

^{R Boed, CC BY 2.0, via Wikimedia Commons}

Resembling something of an undulating matchstick or a standing wave of air, the St. Regis Chicago is one of the newest additions to the Windy City Skyline. With the St. Regis, architect Jeanne Gang earned the honor of having created the world's tallest structure designed by a woman. The building will host a range of luxury properties including nearly 400 condominiums and 200 hotel rooms. The uppermost section of the structure contains unoccupied and open floors, which allow winds to blow through and prevent the rest of the tower from swaying. You might inquire about a hotel room as a way to sneak a peek at the impressive views sure to be on offer in one of Chicago's most iconic new developments. As a bonus, take a stroll through nearby Lake Shore East Park.

[Address] 363 E Wacker Dr, Chicago, IL 60601

NEMA (Chicago) is another new addition to the Chicago skyline and part of the city’s efforts to revitalize areas near the Loop district. NEMA is a high-rise luxury residential development located near Grant Park, the Field Museum, and Soldier Field. Offering impressive views in every direction, NEMA is Chicago's tallest exclusively residential building. Designed by Uruguayan architect Rafael Viñoly, it utilizes a structural bay design that bears resemblance to the Willis Tower when viewed from the right angle. Residential units inside the tower all have expansive floor-to-ceiling windows and the complex features numerous upscale amenities. Snap some impressive photos of NEMA from the southern sections of Grant Park.

[Address] 1210 S Indiana Ave, Chicago, IL 60605

^{James Willamor from Raleigh, NC, USA, CC BY-SA 2.0, via Wikimedia Commons}

875 North Michigan Avenue is 1,128-foot skyscraper located along Chicago's famed Magnificent Mile. Prior to February 2018, it was called the John Hancock Center and is still referred to as such by local Chicagoans and visitors. Architect Bruce Graham adopted a nearly identical design aesthetic to that of the Willis Tower, opting for a black glass and steel exterior topped by twin white spires. Despite not being the tallest building in Chicago, the former John Hancock Center arguably has the city’s best observation deck. 360 Chicago is located on the building's 94th floor and features an innovated tilting glass lookout perched nearly 1,000 feet above the bustling streets below. It's a great place to stop when you're out exploring Michigan Avenue and the Magnificent Mile.

[Address] 875 N Michigan Ave, Chicago, IL 60611

The Tribune Tower is a famed neo-gothic skyscraper located on Michigan Avenue near the Chicago River. The building's iconic design coupled with its placement near DuSable Bridge and the Wrigley Building make it a favored location for photo enthusiasts. The bridge provides excellent views of the surrounding buildings and allows one to really get a sense for Chicago's urban core. Tribune Tower was for many years home to the Chicago Tribune newspaper and of WGN Radio, which famously broadcast from the building's lower floors. Architects John Mead Howells and Raymond Hood won the competition to design the tower in 1922. Construction started a year later and finished in 1925. Each year, Tribune Tower participates in Open House Chicago, an event sponsored by the Chicago Architecture Foundation where visitors can tour the building's interior for free.

[Address] 435 Michigan Ave, Chicago, IL 60611

Located just across Michigan Avenue from the Tribune Tower is the famed Wrigley Building. The two iconic locations appear together in countless photos of downtown Chicago. Originally constructed as the headquarters for the Wrigley Company, the building is now home to several businesses. Despite not being particularly tall, the Wrigley Building has long been a favorite of architecture fans. Designed by Graham, Anderson, Probst & White, the Wrigley Building is one of the firm's iconic works around Chicago, which also include the Field Museum, Shedd Aquarium, and Merchandise Mart. The Wrigley Building's tower borrows its shape from the famed Giralda tower at the Seville Cathedral in Spain. The architects also chose to incorporate elements of the French Renaissance style into the building’s design. Photo hounds will want to position themselves on the opposite side of the Chicago River or on DuSable Bridge for great shots.

[Address] 400-410 Michigan Ave, Chicago, IL 60611

The Aon Center is an iconic Chicago landmark that stands just north of Millennium Park and the Jay Pritzker Pavilion. Completed in 1973, it remains the 4th tallest building in Chicago. Architect Edward Durell Stone used a modern design comprising a tubular steel-framed structure. The white exterior is broken up vertical bands of widows. On sunny days, the Aon Center is easily spotted at the edge of Millennium Park when its surfaces glisten brightly against the blue skies behind. Renovations are currently underway to construct an observation deck that is expected to feature a thrill ride and should open sometime in 2022. A good way to photograph the Aon Center is to head for Buckingham Fountain in Grant Park. From there you can frame the fountain with the Aon Center in the background.

[Address] 200 E Randolph St, Chicago, IL 60601

^{Mobilus In Mobili, CC BY-SA 2.0, via Flickr}

The James R. Thompson Center houses offices for the Illinois state government. It is one of the most important examples of postmodern architecture in Chicago. Constructed in 1985, the exterior uses a sloping glass design that gives the impression of several ring segments stacked one atop the other. The Thompson Center's most impressive features are located inside. A vast open atrium capped by an immense skylight greets visitors when they enter. The colorful interior also features exposed stairs and elevators. The design was purposefully meant to evoke a feeling of openness where government business is conducted in full view of the public. Discussions are underway about renovating or perhaps even replacing the Thompson Center altogether. If for no other reason, now may the best time to see this fascinating architecture achievement in all its controversial glory.

[Address] 100 W Randolph St, Chicago, IL 60601

Marina City is a prize-winning mixed-used residential-commercial complex built alongside the Chicago River. The iconic shell-shaped design gives the appearance of something like two corncobs stood on end. Opened in 1968, Marina City's architectural style is notable for the way it eschews right angles. Interior residential units branch off a circular hallway and progress outward to semi-circular balconies separated by floor-to-ceiling windows. Below the 20th floor there is an exposed parking garage also constructed in a circular pattern. At river level, Marina City does in fact have a small marina, from which the complex takes its name. Visitors to Marina City can enjoy one of several restaurants, a bowling alley, and the Chicago House of Blues music venue. The towers have appeared in numerous film and television shows and are an iconic part of the Chicago skyline.

[Address] 300 N State St, Chicago, IL 60654

The Chicago River runs through the heart of the city. The Chicago Riverwalk is a network of riverside walking paths that offer some of the best views of the amazing skyline. You can hop on and simply start walking, or choose some sections to stroll based on where you're going. One recommendation is to visit the area near Wacker Drive, the Franklin-Orleans Street Bridge, and the Wells Street Bridge. There you can get some great photos where the river curves a bit before heading out to Lake Michigan. You might also consider taking a river cruise, which will ferry you on the river past many of the landmarks featured here in our guide. Finally, take advantage of the Lakefront Trail around Lincoln Park. Going this way will allow you to photograph the skyline looking south. This is another iconic view.

Nighttime shots are some of the best when it comes to the Chicago skyline. The trick is to give yourself a good perspective and make sure you’re able to steady your camera. A prime place to go is Adler Planetarium, which has a long circular walking path offering an ideal view back towards the Loop. You can enjoy time at the planetarium, the Field Museum, and Shedd Aquarium while you’re at it. Another great way to get some nighttime shots is to find one of the city's many rooftop bars. Plenty of hotels in and around the Loop advertise great rooftop bars so you won't have much trouble finding one to visit if you don't mind having to lighten your wallet a bit. Finally, nighttime is a great time to visit the 360 Chicago observation deck in the former John Hancock Center. This is one of the best views of the Chicago skyline and it's made all the more special when the city below is lit up like a blanket of pearls.

Tour Through a Lens (TTAL) bills itself as Chicago's premier custom photography tour. Having reopened now that the COVID-19 pandemic slowed somewhat, TTAL can help you build a custom tour taking into account your preferred dates and times. You bring your camera equipment and the professionals at TTAL will help you find the right locations plus walk you through achieving that amazing shot. They offer several packages including half-day tours, single-focus tours, and total immersion tours. Choose from their available lineups based on your desired subject matter, be it urban scenes, Chicago architecture, landmark buildings, Chicago history, or more. Contact TTAL on their website for more information.

Chicago is a fabulous city and visitors cannot help but marvel at all it has to offer. Whether you're looking for great architecture, food, museums, recreation, or something else, chances are you will find it in Chicago. This year discover the Windy City and take that Chicago vacation you've always wanted.