Feature: with the first Chicago Architecture Biennial kicking off later this week, Dezeen picks 10 of the projects – past and present – that have helped shape the city that gave birth to contemporary high-rise architecture.

New York might be North America's architecture and design capital, but Chicago is where all of the good ideas originally emerged.

In the late 19th and early 20th centuries, groundbreaking architects like Daniel Burnham and Louis Sullivan used the city as an open canvas to develop the steel-frame skyscraper, and to a wider extent, the modern American metropolis. Chicago was mostly destroyed by a fire in 1871, providing early modern architects an unprecedented opportunity to experiment and make their mark.

The city was fertile ground for Frank Lloyd Wright, who lived and worked there in the late 1800s. It was also a welcoming home for International Style architects cast out of the Bauhaus. For Mies van der Rohe and others like him, it was the perfect place to rip off the yoke of Beaux-Arts ornamentalism and start fresh.

Chicago's early 20th century rise as an architectural testing ground came from a wild convergence of immense wealth, available space and civic daring. The international Chicago Architecture Biennial, which opens 3 October and runs through January, will put the spotlight on this legacy. Here, we present 10 of the city's seminal projects:

John Hancock Center, 1969, by Skidmore, Owings & Merrill (SOM)
875 N. Michigan Avenue

The best way to approach the John Hancock Center, one of Chicago's tallest skyscrapers, is from the south, at the intersection of Michigan and Chicago Avenues.

On both sides of Michigan Avenue is the historic Water Tower and Pumping Station, one of the few buildings that survived the 1871 Chicago Fire. Built in 1886, the station consists of crenellated towers that stood tall over the neighbourhood in the late 19th and early 20th centuries. Today it's an aperitif to the 1,500-foot (457-metre) John Hancock Center (including antennas), one block north.

The Hancock building has one of the best-known structural systems in the world. Conceived by SOM's Bruce Graham and engineer Fazlur Khan, the tower's exceptionally efficient system of stacked steel X-braces removed the need for internal support columns. This  – combined with the tower's basalt-black colour, gradually narrowing profile, and symmetrical antennas – makes it the most strapping and muscular tower in a city that prizes itself on tall buildings.

The mixed-use skyscraper contains retail space, parking, offices, residences, and restaurants, and it meets the ground with a sunken elliptical plaza. On the 95th floor, a restaurant and bar are both higher and cheaper to visit than the 94th floor observatory.

McCormick Tribune Campus Center at IIT, 2003, by Office of Metropolitan Architecture (OMA)
3201 S. State Street

The McCormick Tribune Campus Center is one of only a few non-Mies designed buildings at the Illinois Institute of Technology. It also was Rem Koolhaas' first American project. The entire complex squats under an elevated rapid-transit rail line and contains a bookstore, auditorium and food court. A stainless steel tunnel dampens the roar of passing trains.

With its canted lines, bright orange-tinted glass, and free-form intersecting planes, the building is easy to cast as an arrogant boom-era misfit. But despite Koolhaas' intellectual Deconstructivist rigour, the structure shows true reverence for Mies van der Rohe's university campus.

Mies' rectilinear right angles have broken apart and reconfigured to create a procession of sculptural spaces, creating quiet study nooks, as well as bright public spaces. A small patch of prairie grasses on a depressed roof garden – visible from the inside – provides relief from the building's raw, rough materials and dot-matrix glass murals.

Aqua Tower, 2009, by Studio Gang
225 N. Columbus Drive

The best 21st-century addition to Chicago's skyline, Aqua Tower starts with a venerable and well-worn Chicago high-rise trope: the Modernist glass box. But Gang's design adds sculptured whorls of concrete floor slabs that extend beyond the glass facade.

These concrete slabs are fenced off as balconies for the building's apartments, offices and hotel units. Each is custom-designed to give visitors and residents better access to skyline views of the surrounding Loop and Lake Michigan. Together across 82 stories, they appear to ripple like water (hence the name). They also call to mind the limestone rock landforms seen along the banks of the Great Lakes.

Marina City, 1967, by Bertrand Goldberg
300 N. State Street

Organised around a vertical circulation core, the twin Marina City towers feature a tripartite plan. The towers sit on a rectilinear base that contains a multitude of retail and recreation opportunities, all hovering over the Chicago River. The first 20 levels contain a spiralling parking garage, and the top 40 floors are condos, each with their own semicircular balcony. Stacked one atop the other, the balconies resemble kernels on a corncob, the great Midwestern signifier of the land.

Rising 587 feet (180 metres), Marina City was big for its time. When it opened in 1967, it was both the world's tallest apartment tower and the tallest reinforced-concrete building. It also was erected at a time when urban workers were increasingly living in the suburbs. Goldberg's supposition was that people would like to live near where they work, and would do so with the right mix of amenities. So he added a theatre, bowling alley and ice skating rink to the tower.

Art Institute of Chicago, 1893, by Shepley, Rutan and Coolidge; Modern Wing, 2009, by Renzo Piano Building Workshop
111 S. Michigan Avenue

The venerable Art Institute of Chicago has seen more than a half dozen renovations since it opened. The original wing, a grand if somewhat flat Neoclassical design by Shepley, Rutan and Coolidge, was completed in 1893, the year of the epochal World's Columbia Exposition. More than 20 million visitors flowed into Chicago for the fair, taking the image of this grand Greek temple back to their towns to reproduce in their banks, city halls and museums.

One of the few permanent buildings built for the fair, the Art Institute held its influence long after the event. Louis Sullivan complained that its emphasis on classical forms set back American architecture more than half a century.

In 2009, Renzo Piano Building Workshop created the trumpeted Modern Wing. Clad in glass and brilliant white limestone, the structure is an echo of the original building. In addition to galleries, the interior features a daylit court, educational facilities, public amenities and a garden. The building is connected to Millennium Park across the street by a long, thin bridge. During the Chicago Architecture Biennial, the Modern Wing will feature a David Adjaye retrospective in its architecture galleries.

Robie House, 1909, by Frank Lloyd Wright
5757 S. Woodlawn Avenue

One of Frank Lloyd Wright's most favoured projects, the Robie House in Hyde Park is a culmination of his long-simmering meditation on Midwestern landscapes, and precedes the moment when he departed off to more abstracted experiments such as Fallingwater. It has become emblematic of the architect's Prairie Style.

Made of artfully composed horizontal lines of red brick and limestone, the strong terraced layers resemble stratified rock. Inside is a classic Wright composition of dark wood, stained glass and custom-designed high-backed chairs. The house was built for a bicycle and motorcycle manufacturer and was included on the very first National Register of Historic Places list in 1966.

The Rookery, 1888, by Daniel Burnham and John Well
209 S. Lisle Street

Designed by Daniel Burnham  – creator of the famous 1909 Chicago masterplan proposal – and partner John Wellborn Root, The Rookery is an 11-storey office building that was one of the tallest in the world when it opened. Featuring a red granite base with a Romanesque entrance arch, the building is essentially a cube with a hollow core. Its hybrid structural system uses both load-bearing masonry and steel framing.

The building is perhaps best known for its interior Light Court – a double-height atrium with a curving cast-iron staircase and web of steel trusses that enabled natural light to reach office workers deep within the building. In 1905, Frank Lloyd Wright oversaw a renovation of the atrium, simplifying certain decorative elements and installing white marble with Persian-style engravings. It's a rare instance of Wright, at any stage of his career, working on a building by another architect.

Sullivan Center, 1903, by Louis Sullivan
1 S. State Street

This commercial behemoth by Louis Sullivan embodies many design traditions that have made Chicago an architectural epicentre. Formerly the Carson Pirie Scott and Co. Building, the structure is clad in white terracotta. It is one of the best examples of the city's embrace of this fire-resistant material after the Great Fire of 1871.

Massive size has always been a Chicago architecture tradition, and Sullivan Center obliges, taking up almost an entire block. It was an early example of steel framing, climbing 12 stories with a lightweight and efficient structural system. The design pairs vertical elements, like the cylindrical entrance pavilion and tower, with horizontal bands of windows.

The ground floor is covered in a dark cast iron swirl of nature-inspired reliefs, creating a three-dimensional mural of abstracted leaves, branches, and fruits. Today, the building's tenants include a Target department store, the architecture firm Gensler, and the School of the Art Institute of Chicago.

S R Crown Hall at IIT, 1956, by Mies van der Rohe
3360 S. State Street

A floating apparition of glass with a few whiffs of blackened steel, S R Crown Hall – the architecture school for the Illinois Institute of Technology – was designed by Mies van der Rohe while he was dean of the department. The column-free, 25,000-square-foot (2,322-square-metre) building is vast enough to house five basketball courts. With an exceptionally light steel frame, the building reveals what happens when mass is evaporated down to its skeletal essence.

A wide travertine stair brings students to its glass walls and open-air drafting studios arrayed in the massive, airy space. Occasional oak partitions are the only elements dividing the upstairs expanse, and these reach nowhere near the 18-foot-high (5.4-metre) ceiling. This ceiling is suspended from four tall steel-plate girders, which precluded the need for interior columns. The building – an embodiment of the ideals of International Style architects – is regarded as one of the best non high-rise buildings designed by Mies.

Millennium Park, 2004, by SOM (masterplan)
Randolph St. and Michigan Ave

Millennium Park is one of the most significant public spaces created in Chicago in the modern era. Master-planned by SOM, the 24.5-acre (99,000-square-metre) park was built over active commuter rail lines and a parking garage. It features sculptures, a garden, and an outdoor amphitheatre.

From west to east, visitors pass by Doric columns in the Millennium Monument in Wrigley Square, on their way to Anish Kapoor's Cloud Gate. The large, bean-shaped sculpture has a mirrored surface, stretching and distorting views of the surrounding cityscape.

To the east is the Pritzker Pavilion, designed by Frank Gehry. The pavilion is composed of curled ribbons of stainless steel and looks out over an elliptical field criss-crossed by a trellis system that contains speakers.

To the south is Crown Fountain by artist Jaume Plensa and Chicago architects Krueck & Sexton. It features a pair of 50-foot (15-metre) glass blocks that spit out streams of water while projecting faces of Chicago citizens. The southern end of the park also contains Lurie Garden, designed by Kathryn Gustafson, Piet Oudolf and Robert Israel. The 5-acre (20,200-square-metre) park has naturalistic plantings and pays homage to Chicago's motto, Urbs in Horto, or City in a Garden.

Zach Mortice is an architectural journalist based in Chicago. He was formerly the managing editor of the American Institute of Architects' AIA Architect.