#26: Lake Point Tower. To see all 40 of Chicago’s great buildings, launch the gallery »

As the magazine’s earlier Top 40 lists demonstrated, Chicago is justly celebrated for its restaurants and writers, its movies and music, its cultural breakthroughs—even its way with words. But nothing defines the city more than its architecture, a creative and technological discipline in many ways responsible for Chicago’s identity and very existence.

The city’s past is littered with great buildings torn down before their time. For the purposes of this list, I have focused only on buildings that still stand. (To paraphrase the epitaph of the British architect Sir Christopher Wren, if you would see Chicago’s greatness, look around you.) Since architectural and historical significance figured as important criteria, the list is weighted toward older buildings—though recent additions speaks to the city’s ongoing vibrancy. As always, reasoned dissent is welcome. Build your case in the comments section below.

#40: Old St. Patrick’s Church
700 W. Adams St.
(Carter & Bauer, 1856)
Chicago’s oldest public building came together in pieces: the spire and onion dome in 1885, Thomas O’Shaughnessy’s stained-glass windows between 1912 and 1922, and the restored Celtic interior in the 1990s.

#39: Keck-Gottschalk-Keck Apartments
5551 S. University Ave.
(Keck & Keck, 1937)
Coming off their House of Tomorrow at the 1933–34 Century of Progress Exposition, the Keck brothers crafted this simple, energy-conscious three flat.

#38: Contemporaine
516 N. Wells St.
(Perkins + Will, 2004)
Among a crop of leaden residential high-rises, Ralph Johnson’s 15-story concrete tower stands out with its cantilevered balconies.

#37: Second Presbyterian Church
1936 S. Michigan Ave.
(James Renwick, 1874; 1900 renovation, Howard Van Doren Shaw)
A 1900 fire undercut the church’s original neo-Gothic look; Shaw recast the interior in an Arts and Crafts mode, with windows by Louis Tiffany and Edward Burne-Jones.

#36: Market Square
N. Western Ave., Lake Forest
(Howard Van Doren Shaw, 1916)
The U-shaped mall—the country’s first planned shopping center—blends Tyrolean, Italian Renaissance, and other styles.

#35: Frank F. Fisher Apartments
1209 N. State Pkwy.
(Andrew N. Rebori, 1937)
Working with the artist Edgar Miller, Rebori squeezed this Art Moderne structure into a narrow city lot.

#34: Henry B. Clarke House
1855 S. Indiana Ave.
(original architect unknown, 1836; Wilbert Hasbrouck and Joseph Casserly, 1981 restoration)
This Greek Revival residence contends for the title of Chicago’s oldest home.

#33: Carbide and Carbon Building
230 N. Michigan Ave.
(Burnham Brothers, 1929; 2003 restoration by Lucien Lagrange Architects)
The Hard Rock Hotel occupies this gilded Art Deco beauty.

#32: Pullman
neighborhood at E. 111th St. and S. Cottage Grove Ave.
(Solon S. Beman, circa 1880)
Although diminished by the loss of its Administration Building to fire in 1998, this planned industrial community still offers a lively array of brick housing.

#31: Museum of Science and Industry
E. 57th St. and S. Lake Shore Dr.
(D. H. Burnham & Co., 1893; 1930s reconstruction by Graham, Anderson, Probst & White)
The only surviving building from the Columbian Ex-position, where it served as the Palace of Fine Arts. Charles B. Atwood, standing in for the late John Root, executed the neoclassical design.

Photography: Todd Urban

#30: Serta International Center
2600 Forbs Ave., Hoffman Estates
(Epstein, 2009)
The architect Andrew Metter fused a Prairie-style vibe with a spare Miesian grace for this suburban corporate headquarters.

#29: Prudential Building
130 E. Randolph St.
(Naess & Murphy, 1955)
For years Chicago’s tallest building, this limestone behemoth initiated a revival of downtown construction, dormant since the Depression.

#28: NBC Tower
454 N. Columbus Dr.
(Skidmore, Owings & Merrill, 1989)
Adrian Smith’s contribution to the Cityfront Center development updated the 1930s Art Deco style.

#27: 333 West Wacker Drive
(Kohn Pedersen Fox, with Perkins + Will, 1983)
A mix of modern and classical design, William Pedersen’s green-class building mirrors the nearby bend in the Chicago River.

#26: Lake Point Tower
505 N. Lake Shore Dr.
(Schipporeit-Heinrich Associates, with Graham, Anderson, Probst & White, 1968)
Based on a Ludwig Mies van der Rohe design from 1921, its curving glass walls reflect the lakeside setting.

#25: Union Station
210 S. Canal St.
(Graham, Anderson, Probst & White, 1925; 1992 renovation, Lucien Lagrange Architects)
The station’s Great Hall is the last reminder of Chicago’s glory days as the country’s railroad hub.

#24: United Airlines Terminal One Complex
at O’Hare International Airport
(Murphy/ Jahn, with A. Epstein & Sons, 1987)
The soaring barrel-vaulted concourses dazzle—but don’t overlook Helmut Jahn’s functional design.

#23: Wrigley Building
400 N. Michigan Ave.
(Graham, Anderson, Probst & White, 1920, 1924)
Brightly illuminated at night, this wedding cake of a building defies categorization.

#22: Aqua
225 N. Columbus Dr.
(Studio Gang Architects, 2009)
Universally praised for its visual and technical innovation, Jeanne Gang’s rippling Lakeshore East skyscraper found an immediate home on the skyline.

#21: Tribune Tower
435 N. Michigan Ave.
(Howells & Hood, 1925)
Built from a design selected from more than 250 entries to a 1922 contest, this neo- Gothic tower serves as a gateway to the Magnificent Mile.

#20: Aon Center
200 E. Randolph St.
(Edward Durell Stone, with Perkins + Will, 1973)
Chicago’s third- tallest skyscraper lost some of its luster after gray granite replaced its Carrara marble skin.

#19: John J. Glessner House
1800 S. Prairie Ave.
(Henry Hobson Richardson, 1887)
The great East Coast architect’s only surviving Chicago building, its intimidating façade cloaks an airy family haven.

#18: Chicago Water Tower and Pumping Station
806/811 N. Michigan Ave.
(William W. Boyington, 1866, 1869)
A symbol as much as a building, the castellated tower—a survivor of the great fire of 1871—is one of Chicago’s few remaining Boyington works.

#17: Marquette Building
140 S. Dearborn St.
(Holabird & Roche, 1893–1895, 1906)
The brick and terra cotta exterior exemplifies the Chicago style; its entrance and lobby (with its Tiffany mosaics) are among the city’s most stunning.

#16: Richard J. Daley Center
bounded by Washington, Dearborn, Randolph, and Clark streets
(C. F. Murphy Associates; Loebl, Schlossman & Bennett; Skidmore, Owings & Merrill, 1965)
Complemented by the now-beloved Picasso, the rust-colored Cor-Ten steel building rises 648 feet but contains only 31 roomy floors.

#15: Robert Morris Center
403 S. State St.
(William Le Baron Jenney, 1891)
Known historically as the Second Leiter Building, this proto-skyscraper’s steel-and-cast-iron frame—Jenney’s great innovation—led architecture into the modern era.

#14: Marina City
300 N. State St.
(Bertrand Goldberg Associates, 1962)
With their eye-catching corncob design, these twin towers kicked off yet another architectural renaissance in Chicago.

#13: Hotel Burnham
32 N. State St.
(ground floor: Burnham & Root, 1891; rest of building: D. H. Burnham & Co., 1895)
Known originally as the Reliance Building, its façade of broad bay windows anticipated the glassy towers of the later 20th century.

#12: Unity Temple
875 Lake St., Oak Park (Frank Lloyd Wright, 1909)
The cubist exterior cast in unadorned concrete gives way to an awe-inspiring inner chamber.

#11: Inland Steel Building
30 W. Monroe St.
(Skidmore, Owings & Merrill, 1957)
Clad in stainless steel and glass, this postwar gem achieved its open floor plan by banishing elevators and other service elements to a separate tower.

#10: Sears Tower
233 S. Wacker Dr.
(Skidmore, Owings & Merrill, 1974)
The city’s giant is an engineering marvel—and I will never, ever, refer to it as the Willis.

#9: Farnsworth House
14520 River Rd., Plano
(Ludwig Mies van der Rohe, 1951)
A transcendent modernist masterpiece, this glass-walled single-story, single-room house floats elegantly alongside the Fox River.

#8: Frederick C. Robie House
5757 S. Woodlawn Ave.
(Frank Lloyd Wright, 1909)
Prairie style perfected—even Wright had to move in other directions or risk repeating himself.

#7: Auditorium Building
430 S. Michigan Ave.
(Adler and Sullivan, 1889)
Adler’s engineering skills and Sullivan’s design savvy concocted a feast for the ears and the eyes.

#6: S. R. Crown Hall
3360 S. State St.
(Ludwig Mies van der Rohe, with Pace Associates and C. F. Murphy Associates, 1956)
Mies’s clear-span design captures space and light within a deceptively simple glass box defined by steel columns and girders.

#5: Carson, Pirie, Scott & Company
1 S. State St.
(Louis H. Sullivan, 1899, 1903; D. H. Burnham & Co., 1906; Holabird & Root, 1961; major restorations in 1980 and 2010)
Rising from richly ornamented ground floors, the former department store’s spare upper stories showcase serene rows of light-luring Chicago windows.

#4: Monadnock Building
53 W. Jackson Blvd.
(northern half: Burnham & Root, 1891; southern half: Holabird & Roche, 1893)
Massive, austere, and exciting, its mix of steel frame and load-bearing walls signaled the onset of a new age in architecture.

#3: 860–880 North Lake Shore Drive
(Ludwig Mies van der Rohe, with Pace Associates and Holsman, Holsman, Klekamp & Taylor, 1952)
Startling in their day, these 26-story glass towers established the Mies aesthetic and influenced architecture around the world.

#2: The Rookery
209 S. LaSalle St.
(Burnham & Root, 1885–1888; lobbies and light court: Frank Lloyd Wright, 1907)
The celebrated skylit atrium and spiral staircase can unfairly overshadow the building’s audacious exterior and Root’s unseen but ingenious floating foundation.

#1: John Hancock Center
875 N. Michigan Ave.
(Skidmore, Owings & Merrill, 1969)
Bruce Graham, the architect, and Fazlur R. Khan, the structural engineer, paired big-shouldered brawn with cross-braced panache in this defining skyscraper of the second Chicago school of architecture.