Chicago in the 1990s was a vibrant mix of cultural revival, architectural growth, and urban transformation. The city’s skyline continued to expand with iconic additions like the Harold Washington Library Center, while neighborhoods experienced waves of redevelopment and gentrification.
Street scenes in this era capture a city alive with energy and change — bustling sidewalks, elevated trains rattling overhead, colorful storefronts, and the mix of old architecture with emerging modern touches. From downtown’s busy Loop to the character-filled neighborhoods, these moments reflect a decade when Chicago balanced its rich history with a wave of cultural and urban transformation.
These fascinating photos, taken by
Steven Martin, showcase the vibrant street life of Chicago in the 1990s — from bustling downtown to the charm of its diverse neighborhoods.
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| Budweiser ad featuring Harry Caray near Wrigley Field, Chicago, July 1990 |
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| Chicago skyline from John F. Kennedy Expressway, 1990 |
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| Erie Street at Rush, Chicago, March 1992 |
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| Grant Park and skyline, Chicago, March 1992 |
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| Grant Park, Chicago, March 1992 |
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| Holy Name Cathedral from John Hancock Center, Chicago, March 1992 |
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| John G. Shedd Aquarium, Chicago, March 1992 |
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| Lake Street, Chicago, March 1992 |
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| Looking north from John Hancock Center, Chicago, March 1992 |
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| Michigan Avenue, looking north, Chicago, March 1992 |
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| Michigan Avenue, looking north, Chicago, March 1992 |
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| Randolph Street, east of Wabash, Chicago, March 1992 |
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| Snow falling outside Hyatt Regency Hotel, Chicago, March 1992 |
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| Superior Street east of Michigan Avenue, Chicago, March 1992 |
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| Tribune Tower as seen from the Michigan Avenue Bridge, Chicago, March 1992 |
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| View of front entrance of the Hilton Hotel from across Michigan Avenue, Chicago, March 1992 |
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| Adams Street from Wabash Avenue, Chicago, July 1996 |
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| Berghoff Restaurant, Chicago, July 1996 |
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| Buckingham Fountain, Chicago, July 1996 |
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| Chicago River from Michigan Avenue, Chicago, February 1996 |
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| Chicago skyline along the lakefront as it appeared on a winter day in February 1996 |
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| Chicago skyline from Shedd Aquarium, July 1996 |
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| Columbus Drive, Grant Park looking north from Roosevelt Road toward the Prudential and Amoco (now Aon) buildings, Chicago, February 1996 |
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| Dearborn Street, looking south, Chicago, July 1996 |
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| El train turning on the curve from Wabash Avenue to Lake Street in the Loop, Chicago, February 1996 |
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| Holy Name Cathedral, Chicago, February 1996 |
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| John G. Shedd Aquarium, Chicago, February 1996 |
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| Lake Street from Wabash Avenue. The El passes over Lake Street, Chicago, February 1996 |
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| Michigan Avenue from Art Institute Steps, Chicago, July 1996 |
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| Michigan Avenue looking south from Chicago River Bridge, Chicago, February 1996 |
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| Michigan Avenue, looking south, Chicago, February 1996 |
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| Navy Pier at east end, Chicago, July 1996 |
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| North Dearborn Street townhouses, Chicago, February 1996 |
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| Ontario Street, looking west, Chicago, February 1996 |
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| Shedd Aquarium, Chicago, 1996 |
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| The Art Institute of Chicago, July 1996 |
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| Wabash Avenue looking north from Monroe Street, Chicago Loop, July 1996 |
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| Wabash Avenue, looking south from Lake Street, Chicago, February 1996 |
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| Wabash Avenue, looking south from Wacker Drive, Chicago, February 1996 |
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| Wacker Drive West of Michigan Ave., Chicago, February 1996 |
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