1. Skyscraper views
Home of the world’s first skyscraper, Chicago boasts many views from on high. The best views of the city can be seen from the top echelons of the 100-floor, 344-meter (1,128-foot) John Hancock Center. With a swimming pool and a street with shops inside, the John Hancock was designed by Bruce Graham of the legendary architectural firm SOM.
Down on Federal Plaza by the post office, check out the so-called “floating skyscrapers” designed by German-American Ludwig Mies van der Rohe, who transformed downtown Chicago (known as the ‘Loop’) with his modernist architecture school and bold building designs.
2. Experience life in a Frank Lloyd Wright house
What was it like to be modern in 1911? Visit Frank Lloyd Wright’s Robie House, where horizontal lines rule and the fireplace is the heart of the house. It’s located next to the University of Chicago, which owns it.
You can also visit the original home of the famous architect, designer and writer in the residential neighborhood of Oak Park.
3. The Art Institute of Chicago
At the Art Institute of Chicago, one of the best museums in the world, Edward Hopper’s Nighthawks joins George Seurat’s A Sunday Afternoon on the Island of La Grande Jatte and American Gothic by Grant Wood; not to mention a self-portrait by Van Gogh, along with works by Monet, Pollock, Bacon, Picasso, Degas, Hockney, Georgia O’Keeffe, Zurbarán, Dalí, Cézanne and even El Greco.
The Art Institute also features a Modern Wing designed by Pritzker Architecture Prize winner Renzo Piano.
To the south of the so-called “Windy City,” Chinatown is the place to go for brunch on a Sunday. The dim sum, a festival of small, tasty dishes (rolls, dumplings and savory noodles) steamed and served in bamboo steamers, is a must.
5. Millennium Park
In this 21st-century garden, reflections bounce off Anish Kapoor’s sculpture Cloud Gate onto Jaume Plensa’s gushing public art project Crown Fountain. Located next to Lake Michigan and the Art Institute, Millennium Park also features an open-air auditorium designed by Frank Gehry.
6. Jazz at The Green Mill
With over 100 years of history, The Green Mill is possibly the closest you’ll get to Al Capone’s Chicago. Head north to experience the city’s messy and lively side; what it’s like at night under the neon lights. Billie Holiday sang here when it was a speakeasy, and it has plenty of mafia history too.
7. A paradoxical prison
Chicago’s Metropolitan Correctional Center was designed by Harry Weese and built in 1975 with some curious features. It is a vertical prison with a triangular floor plan and windows so narrow they don’t need bars.
8. The Red Flamingo
Alexander Calder’s bold red sculpture Flamingo was a major addition to the city’s aesthetic when it was commissioned and erected in 1974.
Find it in Federal Plaza alongside Ludwig Mies van der Rohe’s floating skyscrapers – the perfect artwork to set off a city full to the brim with art history and architectural design