25 Photos of Chicago Life Through the Years

teenage girl waiting for train
25 Pictures of Chicago Life Through the YearsBettmann - Getty Images

While it may be known as The Windy City, Chicago is home to a lot more than inconvenient weather. Staples such as Wrigley Field have defined this third largest city in the United States. It’s a place where many got their humble beginnings, like Michael Jordan…maybe you’ve heard of him?

Many have walked the streets here, such as Martin Luther King Jr. to advocate for civil rights as well as former President Barack Obama where he and former First Lady Michelle started their careers and life together. Get inspired for your next visit with photos of Chicago life through the years…

While it may be known as The Windy City, Chicago is home to a lot more than inconvenient weather. Staples such as Wrigley Field have defined this third largest city in the United States. It’s a place where many got their humble beginnings, like Michael Jordan…maybe you’ve heard of him? Many have walked the streets here, such as Martin Luther King Jr. to advocate for civil rights as well as former President Barack Obama where he and former First Lady Michelle started their careers and life together. Get inspired for your next visit with photos of Chicago life through the years.

1955

With ads for Old Dutch Root Beer, hotels and businesses were thriving on West Madison Street in Chicago.

west madison street, chicago
Bettmann - Getty Images

1958

We hope firefighters were off to the rescue as a stockyard fire was seen rising above the city over the South Side.

stockyard fire, chicago, 1958
Bettmann - Getty Images

1959

Baseball was just as big back then as it is today in The Windy City. Athletes Dick Klein of the Chicago Bears and Darris McCord of the Detroit Lions shake hands after a game at Wrigley Field.

detroit lions v chicago bears
Robert Riger - Getty Images

1960

An orderly crowd, including Martin Luther King Jr., stood outside the Republican National Convention on the street to advocate for their civil rights platform with signs that read “Human dignity must win”.

demonstrators outside 1960 republican convention
Bettmann - Getty Images

1960

Looking radiant in a dress and heels, this young woman was seen waiting for her train at Union Station. The strike of the Pennsylvania Railroad caused thousands of delays for passengers.

teenage girl waiting for train
Bettmann - Getty Images

1965

Hands held, citizens joined Chicago Freedom Movement members to protest under Chicago L. They called for the termination of school superintendent Benjamin Wills over delays in integrating surrounding schools.

school integration march
Robert Abbott Sengstacke - Getty Images

1966

In an ever-changing landscape, the Twin Towers were hard to miss in this evolving city. Unlike most of the other buildings, these apartment buildings stood out with their circular shape.

view of the twin towers in chicago
Bettmann - Getty Images

1973

Near 43rd and Indiana Avenue, a quiet morning is captured on the South Side of Chicago filled with bustling small businesses and residences.

chicago neighborhood
Smith Collection/Gado - Getty Images

1973

“Thrifty One Stop Shopping” was the tagline to Lake Meadows Shopping Center. Also seen on the South Side is a vintage Kentucky Fried Chicken restaurant (abbreviated today to KFC).

lake meadows shopping center
Smith Collection/Gado - Getty Images

1975

These kids have the moves! Seen on the sidewalk in a residential neighborhood in Chicago with not one, but six children jumping at once!

sidewalk jump rope
Robert Natkin - Getty Images

1979

Did someone say snow day?! The streets were covered in feet of snow after a blizzard which brought more than 20 inches.

cars buried in snow following blizzard
Bettmann - Getty Images

1980

There’s nothing quite like Wrigley Field in Chicago. In a packed stadium, the Chicago Cubs were seen playing the Philadelphia Phillies.

philadelphia phillies v chicago cubs
Jonathan Daniel - Getty Images

1984

Before Oprah became who she is today, she was seen hosting the show ‘AM Chicago’ with the same smile we all know and love.

oprah winfrey hosting 'am chicago'
ABC Photo Archives - Getty Images

1985

Michael Jordan was seen in the early days of his career going for the shot. Number 23 would soon be the player to watch for the Chicago Bulls and a name the whole world will cheer for.

bulls
Focus On Sport - Getty Images

1987

Talent ran the streets of Chicago. Two young men were seen skateboarding and doing one-arm handstands near 87th Street on a sunny day.

young man doing a one arm handstand with a skateboard
Chicago History Museum - Getty Images

1990

The music scene in Chicago has always been top-tier. Rapper Queen Latifah was seen performing a show at the International Amphitheater.

queen latifah live in concert
Raymond Boyd - Getty Images

1997

Words exchanged during the free-throw attempt in the fourth quarter between Kobe Bryant and Michael Jordan just might be the most iconic photo on the internet. The Bulls defeated the Lakers but Bryant, seen here at age 19, had a team-high of 33 points.

los angeles lakers guard kobe bryant and chicag
VINCENT LAFORET - Getty Images

1999

Runners were seen taking part in the 26.2 mile LaSalle Banks Chicago Marathon which is one of the major races known worldwide. Runners come to this coveted event from near and far to participate.

start of marathon
Jonathan Daniel - Getty Images

2010

A couple years into his first term, President Barack Obama was seen speaking at a Democratic event for candidate Alexi Giannoulias at the Drake Hotel.

us president barack obama speaks at
JIM WATSON - Getty Images

2015

Tour boats were seen on the Chicago River past Michigan Avenue. The river draws millions of tourists each year and on Saint Patrick’s Day the water is green!

exploring chicago's river north neighborhood
George Rose - Getty Images

2015

A staple to the city, the Tribune Tower seen here was home to CNN’s Chicago bureau. The landmark is part of the Michigan-Wacker Historic District.

tribune media to sell iconic tribune tower in chicago
Scott Olson - Getty Images

2019

As the leaves were beginning to change, Crown Fountain, Cloud Gate and Jay Pritzker Pavilion can be seen from the aerial view as well as the beloved Bean.

open house chicago 2019
Raymond Boyd - Getty Images

2020

Days before the national lock-down because of COVID-19, tourists explore Millennium Park and visit the Bean up close for that perfect Chicago photo opp.

chicago
KAMIL KRZACZYNSKI - Getty Images

The Obama Presidential Portraits were seen on display at The Art Institute of Chicago. The paintings of Barack Obama by Kehinde Wiley and Michelle Obama by Amy Sherald are now part of the National Portrait Gallery.

obama presidential portraits on display in chicago
Scott Olson - Getty Images

2021

The Navy Pier is the place to be, especially in the summertime! This lakefront destination has something for everyone from restaurants to a ferris wheel, shopping and more.

usa, illinois, chicago, navy pier at lake michigan
Westend61 - Getty Images

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