Many world-famous architects have left their mark on Chicago: Frank Gehry, Frank Lloyd Wright, Jeanne Gang, Sir Anish Kapoor, and of course, the Burnhams. What I love most about Chicago architecture is the diversity of styles. Rather than blending together to form a unified aesthetic, Chicago’s buildings stand out from each other. They pepper the landscape with individual personality. That refusal to conform is pretty emblematic of Chicago as a whole!
It’s hard to distill all the famous architecture in Chicago down to a list of ten, but below are some of my favorites Chicago buildings and the history behind them. Some selections are obvious, some off the beaten path. Some are listed for their aesthetic design, some for the functions they provide. Let us know your favorite Chicago buildings down below in the comments! If you’d like to see more of these Chicago buildings and city architecture up close, and the stories that make them so iconic, our Chicago walking tours and bike tours will take you to many while also giving you the chance to indulge in classic Chicago food.
We’d recommend renting a bike to explore these 10 famous Chicago buildings and other popular areas in the city. Bobby’s Bike Hike offers a range of Chicago bike rentals— from electric to tandem to kids bikes and more.
- Art Institute of Chicago
- Palmer House Hotel
- Baháʼí House of Worship
- Garfield Park Conservatory
- Lincoln Park Conservatory
- The Austin Pink House
- South Shore Cultural Center
- Robie House
- Auditorium Theatre
- Pritzker Pavilion
Famous Chicago Buildings and Interesting Facts About Them
Art Institute of Chicago
It’s not surprising the Art Institute of Chicago is one of the top ten buildings in Chicago to visit. It houses around 300,000 works of art and the second largest collection of impressionist paintings in the entire world. It was built in 1893 for the World Columbian Exposition, and after the conclusion of that grand affair, the Art Institute moved in. While there’s always a new piece to discover each and every visit, I always stop by George Seurat’s painting to sing some Sunday in the Park With George! The museum is free for all children under 14 and all Chicagoans under 18.
Our Chicago Favorites Walking & Food Tour begins right next door to the Art Institute of Chicago at Millennium Park. This tour is one of Bobby’s Bike Hike’s most popular walking food tours. Guests are led through the city on a 2.5-hour tour that includes deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, craft beer (for those 21+), and stops at some of Chicago’s most popular buildings and art pieces such as Cloud Gate, the Pritzker Pavilion, Chicago Theatre, Wrigley Building and more.
Palmer House Hotel
If you wish to visit Chicago and be surrounded by opulence, there’s only one place to stay: The Palmer House Hotel. The hotel was rebuilt after the first Palmer House Hotel was destroyed by the Chicago Fire just 13 days after opening (the dreaded number strikes again!). This was Potter Palmer’s wedding gift to his wife Bertha Honoré. The Palmer House is where everyone who was anyone stayed when visiting the 1893 World Columbian Exposition. Did you know its main ballroom has a secret alcove? If you visit the Empire Room, take a left at the stage and walk towards the mirrored wall. One of these panels is secretly a door. Inside, you can find signed portraits from the various luminaries that have performed there, including Carol Channing and Liberace! And before the parade passes by, make sure you grab one of the Palmer House’s decadent walnut brownies… it’s the original recipe of the original brownie, which debuted at this hotel!
Baháʼí House of Worship
Technically the Baháʼí House of Worship is in Wilmette, but cut me some slack. Wilmette is still in the greater Chicagoland area, the Purple Line express runs there from downtown Chicago, and most importantly, the architecture is gorgeous both inside and out. There are only ten Baháʼí Houses of Worship in the entire world, only one in North America. This is the oldest of the ten, designed by Louis Bourgeois and completed in 1953. Embedded in the architecture you will find symbols of Christianity, Hinduism, Judaism, Buddhism, and Islam, for the Baháʼí belief is that “All the Prophets of God proclaim the same faith.” People of all faith are encouraged to gather and pray here.
Garfield Park Conservatory
The Garfield Park Conservatory is the place to visit when you need a break from the Chicago city buzz. Located right off the Garfield Park Conservatory stop on the Green Line, it’s home to thousands of different plants in temperature-controlled rooms. The mossy fern room is my personal favorite because it’s so serene and tranquil. Kids will especially enjoy seeing the enclave of fruit trees. I was totally astounded at how many grapefruit can grow on a single branch! The Garfield Park Conservatory is also hands-down the best location in Chicago for an engagement photoshoot. Admission is free, although a $5 donation is suggested.
Lincoln Park Conservatory
If your roots are closer to the north side of Chicago instead of the west side, or if you’re a big fan of Susan Orlean’s The Orchid Thief, then the Lincoln Park Conservatory will definitely grow on you! Wandering through the orchid room amidst those colorful, peculiar flowers is like walking through Willy Wonka’s factory. Like a stalwart tree, the Lincoln Park Conservatory has been in its current location since 1893! The ideal time to visit is in the summer months of July and August because the outside Formal Garden is planted in May/June, but you can still see it through October. Like the Garfield Park Conservatory, admission is free.
The Austin Pink House
More of a local Chicago landmark, than a national landmark, the Austin neighborhood’s “Pink House” is brilliantly flamboyant while veering just shy of gaudy and garish (in my opinion, but I have a high tolerance for gaudy). The house itself has existed since 1894, but it was reborn as the pink house in the late 1980s after it was renovated by the Anderson family. The exterior is clearly Victorian. Inside, its southern roots are undeniable in both the rosy color saturation and the sumptuous furnishings. I can’t guarantee you’ll be able to go inside as it is an actual home, but it’s a treasure. If Elle Woods attended Northwestern instead of Harvard, this would be her dream home!
South Shore Cultural Center
Whatever you want in a building, the South Shore Cultural Center has it. A gorgeous location for a wedding reception? The Obamas did that in 1992. A golf course, beach, and picnic area? Check. Restaurant? The Parrot Cage Restaurant is a highly rated eatery, the training ground for student chefs of the Washburne Culinary & Hospitality Institute. The South Shore Cultural Center was originally built in 1905 as an “exclusive” country club (AKA racist and anti-Semitic), but it was later purchased by the Chicago Park District in 1975 to be enjoyed by all.
If rectangles excite you, then Frank Lloyd Wright’s Robie House is a must-visit Chicago building! Who was the eponymous Frederick C. Robie? His father started the Excelsior Supply Company in 1876, which used to sell sewing machine parts before branching out into automobiles and motorcycles. Frederick also worked at Excelsior, but his primary claim to fame is this 1909 house designed by Frank Lloyd Wright, which Robie lived in for less than 2 years. The Robie House is considered one of the prime examples of the Prairie School style of architecture and is located on the campus of the University of Chicago. So if you’re visiting that school as a potential college option, you should stop by the Robie House to take in the famous Chicago building.
It’s certainly controversial to list Adler and Sullivan’s Auditorium Theatre after the Robie House. (Not that these are really ranked in any particular order). The controversy stems from Sullivan having a falling out with Wright, his former protegee, and resulted in them not speaking for 12 years. But speaking of DRAMA, the Auditorium Theatre is beautifully ornate, and you can catch fantastic ballet performances here from the Joffrey and other visiting companies. It wouldn’t be accurate to say that the Auditorium Theatre is the sole reason Chicago was picked over New York to host the 1893 World’s Fair, but President Harrison was at the Auditorium’s opening night performance in 1889, and allegedly turned to Vice President Levi Morton and said, “New York surrenders, eh?”
First off, the Pritzker Pavilion is not a building. I repeat, it’s NOT a building. It’s a… work of art. Due to a very old zoning policy protected by a myriad of court precedent, the Chicago lakefront must be kept “forever open, clear, and free” of buildings. If this were a building, it would violate that order which retailer Montgomery Ward dedicated himself to preserving. So instead, the Pritzker Pavilion is… art.
Why include the not-building in a list of the best Chicago buildings? During the summer, the Pritzker Pavilion hosts amazing concerts from famous musicians of all genres, and they’re entirely free to attend. The pavilion has also been included as a stand-in for so many other (real) Chicago buildings that didn’t make our top 10 to visit. From Pritzker Pavilion, you can see the 83-floor Aon Center, the diamond-shaped roof of the Crain Communications Building, the (whatever-you-call-it) Willis Tower that’s the tallest building in Chicago, Sir Anish Kapoor’s Bean Cloud Gate, Jeanne Gang’s St. Regis Chicago (formerly known as Vista Tower, but names come and go so quickly here), and many more famous Chicago buildings. The Pritzker Pavilion is also not far from the Magnificent Mile, Maggie Daley Park, the Pritzker Military Museum, and the Bobby’s Bike Hike headquarters, where you can rent a bike to visit all popular Chicago buildings (and outdoor art).
Written by Justin Shannin, Bobby’s Bike Hike Tour Guide
I’ve been a tour guide with Bobby’s Bike Hike since 2019, and I often lead the Chicago Favorites Walking & Food Tour. My favorite neighborhood is Uptown/Edgewater because of the independent eateries, proximity to the beach, and cultural diversity. (Try Sun Wah BBQ’s off-menu Beijing DuckDinner, it’s perfection). My favorite part about being a tour guide is introducing people to this wonderful Windy City, which inspires me to learn more about Chicago every day!