Written By: Ben Cosgrove

For the inaugural gallery in our “Great Cities” series, LIFE.com chose to focus on a place that, in so many ways from the triumphant to the deeply troubling remains an emblematic American metropolis. Inspired by these extraordinary pictures, made by LIFE photographers from the 1930s to the 1970s, Chicagoist editor-in-chief Chuck Sudo pays tribute to the town he loves: the Windy City, that toddling town, sweet home Chicago.

Architect Daniel Burnham, whose fingerprints are all over so much of modern Chicago, famously advised, “make no little plans; they have no magic to stir men’s blood and probably themselves will not be realized.”

That, in a proverbial nutshell, is Chicago at its finest: daring to dream and willing to put in the effort to make those dreams reality — whether that means establishing a trading post atop a marsh, rebuilding after a legendary, catastrophic fire or fashioning an iconic skyline that stretches halfway to the heavens. The photos LIFE.com selected to kick off its “Great Cities” series perfectly capture the fully realized dreams of the men and women of Chicago, and epitomize why the 20th century was, so emphatically, “The American Century.”

Passion — daring to dream — permeates the town and, in large part, defines Chicagoans, both native-born and adopted. This is the city that gave us Nelson Algren, Studs Terkel, Gwendolyn Brooks, Carl Sandburg, Roger Ebert, Mike Royko. Chicago is where Oprah Winfrey and Michael Jordan became global superstars. It is the birthplace of the Temperance movement — and it’s where booze flowed like water during Prohibition. Over the decades, its politicians and mobsters have often been indistinguishable from one another, while Chicago’s struggles with poverty, violence and political corruption — like those of any other great, international metropolis — are as old as the city itself.

In the end, though, Chicago’s well-documented woes are as much a part of the city’s fabric as its glories, its triumphs, its world-class cultural achievements.

Daniel Burnham also wrote, “aim high in hope and work, remembering that a noble, logical diagram once recorded will not die, but long after we are gone be a living thing, asserting itself with ever-growing insistence.” Those of us who call ourselves Chicagoans continue to dream big, to reach higher, hoping to add our names to the city’s bold, forever unfolding narrative — and inspire the dreams of future generations in the city we love.

Chuck Sudo is editor-in-chief of Chicagoist. Part of the Gothamist network of local-centric sites, Chicagoist is dedicated to reporting on life in the Windy City in all its facets and in 2012 was named one of Chicago’s top online news sites by the Community Media Workshop. Chuck was born and raised on Chicago’s Northwest side and has called the Bridgeport neighborhood on the South Side home for 15 years. Follow Chuck @bportseasoning.

The El Capitan stopping in Chicago, 1939.

Chicago 1939

Peter Stackpole The LIFE Picture Collection/Getty Images

Crowd of 10,000 at an "America First Committee" rally listening to speeches promulgating isolationism and urging the cutting off of aid to Britain, Chicago Arena, 1941

Chicago 1941

William C. Shrout The LIFE Picture Collection/Getty Images

Chicago, 1941.

Chicago 1941

Horace Bristol The LIFE Picture Collection/Getty Images

Chicago Sun, 1943.

Chicago 1943

Wallace Kirkland The LIFE Picture Collection/Getty Images

Chicago train yard, 1943.

Chicago 1943

Walter Sanders The LIFE Picture Collection/Getty Images

News of the D-Day invasion, Chicago, 1944.

Chicago 1944

Gordon Coster The LIFE Picture Collection/Getty Images

Tenement, West Side of Chicago, 1944.

Chicago 1944

Gordon Coster The LIFE Picture Collection/Getty Images

Chicago, 1944.

Chicago 1944

Gordon Coster The LIFE Picture Collection/Getty Images

Chicago, 1944.

Chicago 1944

Gordon Coster The LIFE Picture Collection/Getty Images

Black Hawks Bill Mosienko (left) and Max Bentley (right), 1946.

Chicago 1946

Frank Scherschel The LIFE Picture Collection/Getty Images

Stranded during a railroad strike, Chicago, 1946.

Chicago 1946

Mark Kauffman The LIFE Picture Collection/Getty Images

People gathering on the street to watch a satire of political officials, Chicago, 1947.

Chicago 1947

Wallace Kirkland The LIFE Picture Collection/Getty Images

Children in a junk-littered lot, Chicago, 1947.

Chicago 1947

Walker Evans The LIFE Picture Collection/Getty Images

Chicago, 1947.

Chicago 1947

Walker Evans The LIFE Picture Collection/Getty Images

The Empire State Express at the Chicago Railroad Fair, 1948.

Chicago 1948

George Skadding The LIFE Picture Collection/Getty Images

Children watch a giant animated figure of Paul Bunyan, Chicago, 1949.

Chicago 1949

Francis Miller The LIFE Picture Collection/Getty Images

The Y.M.C.A. hotel, Chicago, 1951.

Chicago 1951

Ralph Crane The LIFE Picture Collection/Getty Images

Chicago nightclub, 1952.

Chicago 1952

Gjon Mili The LIFE Picture Collection/Getty Images

Legendary Chicago club owner Matt Schulien entertains patrons, 1952.

Chicago 1952

Gjon Mili The LIFE Picture Collection/Getty Images

The Sea Restaurant, Chicago, 1952.

Chicago 1952

Wallace Kirkland The LIFE Picture Collection/Getty Images

Michigan Senator Blair Moody (right) and Franklin D. Roosevelt Jr. confer during the 1952 Democratic National Convention in Chicago.

Chicago 1952

Hank Walker The LIFE Picture Collection/Getty Images

Aerial view overlooking network of tracks for some 20 major railroads converging on Union Station (upper left), Chicago, 1954.

Chicago 1954

Andreas Feininger The LIFE Picture Collection/Getty Images

Cleveland-Chicago game, 1954.

Chicago 1954

Francis Miller The LIFE Picture Collection/Getty Images

Prudential Building, Chicago, 1954.

Chicago 1954

John Dominis The LIFE Picture Collection/Getty Images

Ernie Banks, 1955.

Chicago 1955

John Dominis The LIFE Picture Collection/Getty Images

Chicago detectives force their way into an apartment, 1957.

Chicago 1957

Gordon Parks The LIFE Picture Collection/Getty Images

Poet Carl Sandburg looks out a window in the Chicago Board of Trade Building, 1957.

Chicago 1957

Grey Villet The LIFE Picture Collection/Getty Images

Bill Klose, Cub fan who threw out first ball of season, 1957.

Chicago 1957

Frank Scherschel The LIFE Picture Collection/Getty Images

Ted Williams waits while pitcher warms up at Comiskey Park, 1957.

Chicago 1957

Frank Scherschel The LIFE Picture Collection/Getty Images

Chicago, 1957.

Chicago 1957

Francis Miller The LIFE Picture Collection/Getty Images

Chicago, 1957.

Chicago 1957

Francis Miller The LIFE Picture Collection/Getty Images

Stunt man Jack Wylie flying over the Chicago River, 1958.

Chicago 1958

Al Fenn The LIFE Picture Collection/Getty Images

Midway Airport, 1960.

Chicago 1960

Robert W. Kelley The LIFE Picture Collection/Getty Images

Chicago garage, 1961.

Chicago 1961

Andreas Feininger The LIFE Picture Collection/Getty Images

Chicago, 1961.

Chicago 1961

Andreas Feininger The LIFE Picture Collection/Getty Images

Mies van der Rohe buildings, Chicago, 1961.

Chicago 1961

Andreas Feininger The LIFE Picture Collection/Getty Images

Dick Butkus in a game against the Rams, 1965.

Chicago 1965

Bill Eppridge The LIFE Picture Collection/Getty Images

Chicago welcomes astronauts James McDivitt and Ed White, 1965.

Chicago 1965

Robert W. Kelley The LIFE Picture Collection/Getty Images

National Guardsmen in front of a store during riots following the murder of Martin Luther King Jr., Chicago, April 1968.

Chicago 1968

Lee Balterman The LIFE Picture Collection/Getty Images

O'Hare Airport, 1970.

Chicago 1970

Co Rentmeester The LIFE Picture Collection/Getty Images

A TWA plane lands at O'Hare, 1970.

Chicago 1970

Co Rentmeester The LIFE Picture Collection/Getty Images

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