10 Places To See Amazing Architecture in Chicago

From its earliest days, Chicago’s urban architecture has always stood tall as historic, innovative, and world-class. The impressive skyline reflects a variety of ground-breaking building styles emanating from visions of the city pioneers. Designers like Daniel Burnham, Mies Van der Rohe, Helmut Jahn, Louis Sullivan, and Jeanne Gang all contributed to the magnificent skyline that borders the Chicago River and Lake Michigan.

Chicago became one of the world’s largest cities in less than 100 years, thanks in large part to its incredible architecture. I’ve lived in the city for 20  years and am sharing a few of my favorite must-sees for your trip to Chicago. Get a glimpse of these marvels and learn what you should see and do when you visit in this handy travel guide.  

1. Discover the Chicago Architectural Center

One of the best places to start your exploration of Chicago’s famous architectural wonders is the Chicago Architecture Center, located next to the river at 111 E. Wacker Drive. 

The CAC opened its current facility in 2018, and now offers more than 70 tours showcasing the city’s fabulous architecture, neighborhoods, and skyline. Exhibits feature Chicago’s continued leading role in the design of skyscrapers that have changed the skylines of cities around the world. Other exhibits let you imagine what urban life will look like in 2050.

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Travel tip: The CAC sponsors a yearly open house scheduled this year for October 14 and 15, 2023. Admission is free.

2. Walk the Chicago Riverwalk

Chicago’s Riverwalk is almost like a city unto itself, lined with restaurants and bars along the river, perfect for people-watching. The 1.25-mile path features different districts like the Confluence, Arcade, and Esplanade. Learn more in our guide to everything to see on the Chicago Riverwalk.

Enjoy a cocktail or a meal as the current of the river changes. Dining establishments along the river like Beat Kitchen, City Winery, and Chicago Brewery feature a range of Chicago’s best food and drinks. (There’s even gelato!)

Walk along the pedestrian trail and notice the cool sculptures that represent the city of Chicago. The Riverwalk Gateway, for instance, designed by one of Chicago’s leading architectural firms, Skidmore, Owings, and Merrill, links the Chicago River with the lakefront.

Check out the 28 ceramic panels that create a pictorial narrative of the history of Chicago as well as the river.

On our Chicago River Architecture Walking Tour, you’ll learn even more about the river — like why it flows backward and how they dye it green for St. Patrick’s Day — and the amazing architecture that surrounds it.

3. Explore the Chicago Cultural Center

One of the most visited sites in Chicago is the Chicago Cultural Center, built in the Classical Revival style in 1897 as the first centrally located public library.

The “People’s Palace” took on a whole new role in 1991 when it was repurposed as the Chicago Cultural Center offering theater, events, dance performances, and concerts throughout the year.

What’s unique about this building is that it boasts not one but two exquisite glass domes. On the south side of the building in Preston Bradley Hall, the interior features the largest Tiffany glass dome in the world, spanning more than 1,000 square feet. It’s made up of more than 30,000 pieces of glass. If you think the glass resembles fish scales, that’s because it was designed to.

The second dome is on the north side of the building, 40 feet in diameter designed in a traditional Renaissance pattern.

Tip: Take a free guided tour to get a better understanding of the hidden secrets of this amazing building. Tours take place every Thursday and Friday at 1:15 p.m.

4. Shop the Magnificent Mile

Traditionally known for its high-end shopping, the Magnificent Mile — and 8-block stretch on Michigan Avenue — is also home to luxury hotels, skyscrapers, and other historic buildings like the original Water Tower, built in 1869. Walk down this iconic street to window shop at Gucci, Louis Vuitton, Neiman-Marcus, Barney’s of New York, and lots more. 

You’ll also spot plenty of restaurants and specialty shops like the just-opened Ukraine Cultural Showcase pop up shop, now through October 13. 

5. Walk among the clouds at the Willis Tower

Originally built as the Sears Tower in 1974, the Willis Tower is home to one of Chicago’s most popular attractions, the Skydeck, located on the 103rd floor.

But before you shoot up for the skies, start at the street level with the interactive museum outlining Chicago’s history as a city on the river.

You’ve probably seen pictures of people standing on the ledge, a glass floor balcony that juts out from Willis Tower. Try it, if you dare — it’s well worth it!

Learn more about the history of the Skydeck in the Skydeck Theatre.  You get exquisite panoramic views of Chicago’s skyline from this highest point in the city as well as Chicago’s other landmarks such as Navy Pier and Wrigley Field. On a clear day, they say you can see more than 50 miles.

Plan ahead: Advance reservations are recommended for Willis Tower. 

6. Admire the towering John Hancock Center

Built in 1969 and reaching 100 stories, the John Hancock Center used to be the tallest building in Chicago way before Sears Tower was even on the drawing board. Now a trip to the top offers some amazing things to do.

Go to the 360 CHICAGO Observation Deck at 1,030 feet above the Magnificent Mile, and you can see what looks like forever. You’ll glimpse four neighboring states: Illinois, Wisconsin, Indiana, and Michigan.

You’ll also find TILT — Chicago’s highest thrill ride, where you literally tilt over the edge on this moving platform. Grab a drink before or after.

For a bit of a splurge, dine in style at the Signature Room on the 95th floor for exquisite views of Chicago and Lake Michigan or have a drink at CloudBar on the ninth floor. 

7. Walk Chicago’s loop bridges

Crossing bridges in Chicago is a natural because the Chicago River runs through the city. Within a mere two miles, there are 18 moveable bridges representing a range of architectural styles. Fact is, Chicago has more drawbridges than any other city in the U.S. 

Walking along Wacker Drive is the best place to see many of these bridges. Notice the iconic steel bascule bridges and double-decker bridges that cross over lower Wacker Drive. The Michigan Avenue Bridge, also called the Du Sable Bridge, is over 100 years old.  

Photo tip: Get the best views of the city from the Michigan Avenue Bridge.

8. Sail on an architecture cruise

You can also admire Chicago’s architectural jewels from the water with a cruise on the river and Lake Michigan. Get a true sense of history and place in Chicago’s 130 years of design innovation. 

Chicago’s architecture is really diverse, revealing a skyline with structures built from 1920 to 2020. You will see how many older buildings that were once factories have now been repurposed as condos and galleries.

Travel tip: Be sure to bring a hat and maybe gloves because it is cooler on the water, and especially if you go out on Lake Michigan. There’s an expression in Chicago that says, “cooler by the lake.” I say it’s even cooler on the lake.

9. Take a selfie at the Bean

Often called “Cloud Gate,” The Bean has become the icon of the city. Located in Millennium Park between Randolph and Monroe, The Bean was designed by British artist Anish Kapoor and opened in 2004 as Chicago’s pride and joy of public art. 

It’s made up of more than 150 steel plates that have been welded together, allowing you to stand near it and see the whole skyline. People like to look inside as well for a different perspective. 

Fun fact: The Bean also has an AI app to help you plan your trip to Chicago or what to do when you get here.

10. Check out the Union Carbide and Carbon Building

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For the best example of art deco architecture, the Union Carbide and Carbon Building at 230 N. Michigan shines all the way to the top. 

In the 1920s, Chicago was a bastion of glitz and glamour. The top of the UC&C building was designed to look like a champagne bottle, ready to pop, and finished with, yes, real gold.

Learn more about Chicago’s architecture scene

Discover more about Chicago’s fascinating architecture on our Chicago River Architecture Walking Tour. Your local guide will share secrets of the city, the river, and our history while pointing out some of the best architecture highlights and details. Plus, you’ll get tips for more ideas on what to do on your visit to Chicago.

I hope this post inspired you to explore more of this city’s treasures, from bridges to domes to skyscrapers and beyond!