Written By: Ben Cosgrove

 Inspired by these extraordinary pictures, made by LIFE photographers from the 1930s to the 1970s, Chicago-based journalist 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 here perfectly capture the 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 was born and raised on Chicago’s Northwest side. Follow Chuck @bportseasoning.

The El Capitan stopping in Chicago, 1939.

The El Capitan stopping in Chicago, 1939.

Peter Stackpole The LIFE Picture Collection/Shutterstock

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

A crowd of 10,000 at an “America First Committee” rally listened to speeches promulgating isolationism and urging the cutting off of aid to Britain, Chicago Arena, 1941

William C. Shrout The LIFE Picture Collection/Shutterstock

Chicago, 1941.

Chicago, 1941.

Horace Bristol The LIFE Picture Collection/Shutterstock

Chicago Sun, 1943.

Chicago Sun newspaper, 1943.

Wallace Kirkland The LIFE Picture Collection/Shutterstock

Chicago train yard, 1943.

Chicago train yard, 1943.

Walter Sanders The LIFE Picture Collection/Shutterstock

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

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

Gordon Coster The LIFE Picture Collection/Shutterstock

Tenement, West Side of Chicago, 1944.

Tenement, west side of Chicago, 1944.

Gordon Coster The LIFE Picture Collection/Shutterstock

Chicago, 1944.

Chicago, 1944.

Gordon Coster The LIFE Picture Collection/Shutterstock

Chicago, 1944.

Chicago, 1944.

Gordon Coster The LIFE Picture Collection/Shutterstock

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

Chicago Blackhawks players Bill Mosienko (left) and Max Bentley (right), 1946.

Frank Scherschel The LIFE Picture Collection/Shutterstock

Stranded during a railroad strike, Chicago, 1946.

Commuters were stranded during a railroad strike, Chicago, 1946.

Mark Kauffman The LIFE Picture Collection/Shutterstock

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

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

Wallace Kirkland The LIFE Picture Collection/Shutterstock

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

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

Walker Evans The LIFE Picture Collection/Shutterstock

Chicago, 1947.

Chicago, 1947.

Walker Evans The LIFE Picture Collection/Shutterstock

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

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

George Skadding The LIFE Picture Collection/Shutterstock

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

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

Francis Miller The LIFE Picture Collection/Shutterstock

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

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

Ralph Crane The LIFE Picture Collection/Shutterstock

Chicago nightclub, 1952.

Chicago nightclub, 1952.

Gjon Mili The LIFE Picture Collection/Shutterstock

Legendary Chicago club owner Matt Schulien entertains patrons, 1952.

Legendary Chicago club owner Matt Schulien entertained patrons, 1952.

Gjon Mili The LIFE Picture Collection/Shutterstock

The Sea Restaurant, Chicago, 1952.

The Sea Restaurant, Chicago, 1952.

Wallace Kirkland The LIFE Picture Collection/Shutterstock

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

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

Hank Walker The LIFE Picture Collection/Shutterstock

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

An aerial view overlooked the network of tracks for some 20 major railroads converging on Union Station (upper left), Chicago, 1954.

Andreas Feininger The LIFE Picture Collection/Shutterstock

Cleveland-Chicago game, 1954.

The Cleveland Indians played the Chicago White Sox, 1954.

Francis Miller The LIFE Picture Collection/Shutterstock

Prudential Building, Chicago, 1954.

Prudential Building, Chicago, 1954.

John Dominis The LIFE Picture Collection/Shutterstock

Ernie Banks, 1955.

The beloved Ernie Banks of the Chicago Cubs, 1955.

John Dominis The LIFE Picture Collection/Shutterstock

Chicago detectives force their way into an apartment, 1957.

Chicago detectives forced their way into an apartment, 1957.

Gordon Parks The LIFE Picture Collection/Shutterstock

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

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

Grey Villet The LIFE Picture Collection/Shutterstock

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

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

Frank Scherschel The LIFE Picture Collection/Shutterstock

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

Boston’s Ted Williams waited while a White Sox pitcher warmed up at Comiskey Park, 1957.

Frank Scherschel The LIFE Picture Collection/Shutterstock

Chicago, 1957.

Chicago, 1957.

Francis Miller The LIFE Picture Collection/Shutterstock

Chicago, 1957.

Chicago, 1957.

Francis Miller The LIFE Picture Collection/Shutterstock

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

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

Al Fenn The LIFE Picture Collection/Shutterstock

Midway Airport, 1960.

Midway Airport, 1960.

Robert W. Kelley The LIFE Picture Collection/Shutterstock

Chicago garage, 1961.

Chicago garage, 1961.

Andreas Feininger The LIFE Picture Collection/Shutterstock

Chicago, 1961.

Chicago, 1961.

Andreas Feininger The LIFE Picture Collection/Shutterstock

Mies van der Rohe buildings, Chicago, 1961.

Mies van der Rohe buildings, Chicago, 1961.

Andreas Feininger The LIFE Picture Collection/Shutterstock

Dick Butkus in a game against the Rams, 1965.

Bears linebacker Dick Butkus in a game against the Rams, 1965.

Bill Eppridge The LIFE Picture Collection/Shutterstock

Chicago welcomes astronauts James McDivitt and Ed White, 1965.

Chicago welcomed astronauts James McDivitt and Ed White, 1965.

Robert W. Kelley The LIFE Picture Collection/Shutterstock

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

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

Lee Balterman The LIFE Picture Collection/Shutterstock

O'Hare Airport, 1970.

O’Hare Airport, 1970.

Co Rentmeester The LIFE Picture Collection/Shutterstock

A TWA plane lands at O'Hare, 1970.

A TWA plane landed at O’Hare, 1970.

Co Rentmeester The LIFE Picture Collection/Shutterstock

More Like This

destinations

Wild and Frozen: Minnesota at Its Coldest and Most Remote

destinations

Oh, To Be Young and in Aspen

destinations

“The Most Thrilling Ride in the U.S.”

destinations

Mysterious Italy: The Mummies of Venzone

destinations

Seeking Warmth During an Iceland Deployment

destinations

Diving For Abalone: A Vanishing Tradition