Flag Stop 4,614 transit photos from Chicago and beyond, mostly 1940s–2000s
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1449 photographs
A vintage city bus at night, with its destination sign reading 16-Cicero and fleet number 3605 visible on the side and front. A Chicago Transit Authority New Look bus, number 3605, is shown at night on the 16-Cicero route. 1961 · 16th and Cicero, Chicago, IL A vintage green and cream CTA bus, number 2505, is shown from a front three-quarter view on a city street, with a large brick building labeled 'Cadillac Glass Co.' in the background. A Chicago Transit Authority New Look bus, number 2505, on the 21 McCormick Place route, parked in front of the Cadillac Glass Co. building in Chicago. 1961 · Cermak and Peoria, Chicago, IL A vintage motor bus with a cream top and dark lower body, displaying route 21 to McCormick Place, is shown on a city street in front of a large brick building with 'Cadillac Glass Co.' painted on its side. A Chicago Transit Authority New Look bus, number 2505, on route 21 to McCormick Place, photographed on a sunny day in front of a Cadillac Glass Co. building in Chicago. 1961 · Cermak and Peoria, Chicago, IL A cream and dark green CTA bus with the number 1612 on its front and rear, showing the destination '6 LAKE-AUSTIN' on its sign, driving down a street with a Standard Oil sign and bare trees in the background. A Chicago Transit Authority New Look bus, number 1612, on route 6 Lake-Austin, captured on a winter day in the 1960s. 1961 · Lake and Central, Chicago, IL A black and white photo of a CTA bus numbered 137 on a city street, with passengers boarding. The Chicago Water Tower and a tall building are visible behind it. A Chicago Transit Authority New Look bus, number 137, picks up passengers at a downtown bus stop with the Chicago Water Tower in the background. 1961 · Chicago, IL A three-quarter front view of a vintage Chicago Transit Authority motor bus, number 0103, painted green and silver, with a destination sign reading '21 MC CORMICK PLACE' and a side sign reading 'CERMAK'. A Chicago Transit Authority New Look bus, number 0103, in its green and silver livery, marked for the 21 Cermak route to McCormick Place. 1961 · 77th and Vincennes, Chicago, IL A nighttime street scene showing a line of Chicago Transit Authority buses on a busy, illuminated downtown street with Christmas decorations and pedestrians on the sidewalks. A Chicago Transit Authority GM New Look bus, number 5968, lines up on a decorated downtown street at night, likely during the winter holiday season of the 1960s. 1961 · State and Van Buren, Chicago, IL A vintage CTA bus with the number 3662 on its front, parked on a street with wet pavement in winter, with a car wash and bare trees visible in the background. A Chicago Transit Authority Flxible New Look motor bus, number 3662, displaying route 82 to Lawndale, is parked on a wet street in winter, with bare trees and a car wash in the background. 1961 · Devon and Kedzie, Chicago, IL Front view of a vintage white and dark-colored bus with route 90 Grand-Harlem Center on its sign, driving on a city street next to a large brick building under an overcast sky. A Chicago Transit Authority Flxible New Look bus, numbered 1743, operates on route 90 Grand-Harlem Center along a street lined with a brick building. 1961 · 90 and Harlem, Chicago, IL A black-and-white night scene of a city street with several buses, including a lead bus numbered 5968, surrounded by holiday lights and storefronts with people on the sidewalks. A Chicago Transit Authority Flxible New Look bus, number 5968 on route 36 to Illi-Morgan, travels down a festive, illuminated State Street at night. 1961 · State and Van Buren, Chicago, IL A vintage black and white photo of a Chicago Transit Authority bus on a city street, with a Ben-Bey sign on a building and other buses in the background. A Chicago Transit Authority Flxible Metro bus, number 5009, on route 62 Devon-Redz in Logan Square, with other buses and a Ben-Bey storefront visible. 1961 · Logan Square, Chicago, IL A green and cream CTA trolleybus numbered 9355 on route 85 Central-Harrison travels down a sunny, snow-dusted street lined with storefronts and power lines. Chicago Transit Authority trolleybus 9355 on route 85 Central-Harrison in winter, with overhead wires and a storefront sign for 'Cokes THE PEAK OF ALL Candies' visible. February 1961 · Belmont and Central, Chicago, IL A green and cream CTA trolleybus, number 9763, is parked on a snowy street with overhead wires, near a 1950s car and apartment buildings. A Chicago Transit Authority trolleybus, number 9763, on route 65 Milwaukee-Halsted in winter, with snow and slush on the street. February 1961 · Octavia and Belmont, Chicago, IL Front three-quarter view of a green and cream CTA trolleybus, number 9355, on route 85 Central-Harrison, with overhead wires and storefronts in the background. A Chicago Transit Authority trolleybus, number 9355, on route 85 Central-Harrison, navigating a city street on a clear winter day. February 1961 · Central and Belmont, Chicago, IL A green and cream trolleybus numbered 9763 is parked on a wet, snowy street under overhead wires, with apartment buildings and bare trees in the background. A Chicago Transit Authority Flxible New Look trolleybus, number 9763, on the Belmont-Halsted route in winter, with snow on the ground and bare trees in the background. February 1961 · Belmont and Octavia, Chicago, IL A green and cream Chicago Transit Authority trolleybus, number 9763, on route 11 Belmont-Halsted, is parked on a snow-covered street with bare trees and apartment buildings in the background. A Chicago Transit Authority Flxible New Look trolleybus, number 9763 on route 11 Belmont-Halsted, is stopped on a snowy street in the 1960s. February 1961 · Belmont and Octavia, Chicago, IL A green and cream trolleybus with the number 9355 and route 85 Central-Harrison is stopped on a street, with several vintage cars around it and bare trees in the background. Chicago Transit Authority trolleybus 9355 on route 85 Central-Harrison, surrounded by 1950s automobiles on a winter day. March 1961 · Central and Fullerton, Chicago, IL A green and cream trolleybus with the number 9355 and destination sign reading '85 CENTRAL-HARRISON' is on a city street lined with vintage cars and bare trees, with a 'Henry's Hamburgers' sign visible on the left. A Chicago Transit Authority trolleybus, number 9355, on route 85 to Central-Harrison, shares the street with vintage automobiles near the intersection of Central and Fullerton Avenue in the early 1960s. March 1961 · Central and Fullerton, Chicago, IL A vintage CTA bus numbered 2503 is parked on a city street, displaying a route sign for '58 25 LARAMIE' and an ad for 'Magikist' dry cleaners, with 1950s cars in the background. CTA bus 2503, a Flxible model, is shown at a street corner in Chicago with its destination sign reading '58 25 LARAMIE' and a 'Magikist' advertisement on the front. April 29, 1961 · 25th and Laramie, Chicago, IL A green and cream Chicago Transit Authority bus, number 3593, is turning at a downtown intersection with pedestrians and classic cars nearby, under a clear blue sky. A Chicago Transit Authority New Look bus, number 3593, on route 60 to Kenton, turns at an intersection in downtown Chicago on a sunny spring day. April 29, 1961 · Monroe and Dearborn, Chicago, IL A vintage city bus, number 2508, is shown driving down a city street with storefronts and parked cars on either side under a clear sky. A Chicago Transit Authority New Look bus, number 2508, operates on route 58 Ogden-Downtown at the intersection of Ogden and Cermak in the early 1960s. April 29, 1961 · Ogden and Cermak, Chicago, IL A vintage green and cream bus with the number 2503 on its front is parked on a city street, with a 1950s station wagon visible in the background. A Chicago Transit Authority New Look bus, fleet number 2503, on the 58 Laramie route, stopped on a city street in the early 1960s. April 29, 1961 · 25th and Laramie, Chicago, IL A green and cream CTA bus numbered 3639 is driving down a city street on an overcast day, with a vintage car parked across the street. A Chicago Transit Authority New Look bus, number 3639, on a street in Chicago, likely at the Cermak and Harlem intersection, in the 1960s. May 1961 · Cermak and Harlem, Chicago, IL A green and cream CTA bus with the number 129 and route 58 Ogden-Downtown on its front sign, driving down a wide street with a large building in the background. A Chicago Transit Authority New Look bus, number 129, on route 58 Ogden-Downtown, captured in action on a city street. May 1961 · Ogden and Damen, Chicago, IL An elevated view of a green and red electric train on a steel viaduct in a city, with 1950s cars on the street below. A Chicago North Shore and Milwaukee electric multiple-unit train, car 716 leading, travels on its elevated structure in Chicago on a clear day. September 5, 1961 · State and 8th, Chicago, IL An elevated black and white photograph shows two Chicago Transit Authority buses on a wide city street next to a park with a tall monument, surrounded by 1960s cars and pedestrians. Chicago Transit Authority Flxible New Look buses, including number 2013, navigate a busy intersection near Logan Square park in the 1960s. 1962 · Logan Square, Chicago, IL A front view of a Chicago Transit Authority bus numbered 137, parked at a curb with passengers boarding, with the Chicago Water Tower and city skyline behind it. A Chicago Transit Authority New Look bus, number 137, picks up passengers at a downtown bus stop with the historic Chicago Water Tower in the background. 1962 · Chicago, IL A vintage cream and green CTA bus with the number 1743 on its front is driving down a road lined with trees showing fall colors. A bus stop sign for Peterson is visible on the left. A Chicago Transit Authority Flxible New Look bus, number 1743, on route 84 Caldwell-Central, is pictured driving on a tree-lined street in autumn. October 6, 1962 · Peterson and Oakley, Chicago, IL A green and cream Chicago Transit Authority bus with the number 1732 is turning a corner on a city street, with storefronts and a large billboard for Miller beer in the background. A Chicago Transit Authority Flxible New Look bus, number 1732, on route 04 Caldwell - Cinkal, driving past Heine mann's store on a street corner in Chicago during the 1960s. October 6, 1962 · Ridge and Broadway, Chicago, IL Two cream and green Chicago Transit Authority trolleybuses with overhead wires drive down a busy city street decorated for Christmas, with Walgreens and other storefronts visible in the background. Two Chicago Transit Authority trolleybuses, numbers 8482 and 8254, travel through a festively decorated downtown Chicago street during the winter holiday season. December 15, 1962 · State and Jackson, Chicago, IL A Chicago Transit Authority trolleybus with the number 8073, running on route 36, is shown on a decorated city street lined with 1950s cars and a Walgreens store. Chicago Transit Authority trolleybus #8073 on route 36 Broadway-Devon, navigating a festively decorated downtown street in the late 1950s or early 1960s. December 15, 1962 · State and Jackson, Chicago, IL A green and cream trolleybus with the number 8073 on its front is driving down a decorated downtown street lined with tall buildings and vintage cars, with pedestrians walking on the sidewalk. A Chicago Transit Authority Flxible trolleybus, number 8073, runs on route 36 Broadway-Se Fer through downtown Chicago's State Street during the holiday season, circa 1957-1962. December 15, 1962 · State and Jackson, Chicago, IL A green and cream Chicago Transit Authority trolleybus, number 9326, is driving on a street with overhead wires, with a truck beside it and an overpass in the background. CTA trolleybus 9326 on route 95 to Central Harbour, driving on a city street under an overpass in winter. 1963 · Central and Kennedy, Chicago, IL A black and white photo of a Chicago Transit Authority bus, number 5240, elevated on a lift inside a large garage, with its destination sign reading 'ELSTON-ARMSTRONG' and an ad for Drewry's beer on the front. Chicago Transit Authority bus 5240, a Flxible New Look, suspended for maintenance inside the Forest Glen Garage in the 1950s. 1963 · Forest Glen Garage, Chicago, IL A vintage electric interurban car with a streamlined body and trolley pole is parked at a snowy station platform on an elevated railway at night in a city setting. A Chicago North Shore and Milwaukee Master Unit interurban car, #801, stands at a snow-dusted station platform at night on an elevated structure in Chicago. January 20, 1963 · 6th and Clybourn, Chicago, IL A green and cream CTA trolleybus, number 9374, is turning at an intersection under overhead wires, with buildings and a vintage car in the background. A Chicago Transit Authority trolleybus, number 9374, operates on the 78 Montrose-Broadway route at a street intersection under a web of overhead wires. June 12, 1963 · Montrose and Elston, Chicago, IL Two red Canadian Pacific diesel locomotives, numbered 3050 and 4620, sit side-by-side on a gravel track with bare trees in the background under an overcast sky. Two red Canadian Pacific GP9 diesel locomotives, numbers 3050 and 4620, are coupled on a private right-of-way, with bare trees in the background indicating a winter scene. April 12, 1964 · York and Irving Park, Chicago, IL A red Canadian Pacific diesel locomotive, numbered 8540, sits on a railway track beside a road with bare trees in the background. Canadian Pacific GP9 diesel locomotive 8540, in its iconic red and black livery, is coupled to another unit, 8533, on a private right-of-way near a road. August 1964 · York and Irving Park, Chicago, IL A red Canadian Pacific diesel locomotive numbered 8540 is shown on a railroad track with bare trees in the background. A Canadian Pacific GP9 locomotive, number 8540, leads a consist on a mainline track during winter. August 1964 · York and Irving Park, Chicago, IL A green and cream streetcar numbered 1144 turns on curving street track beneath overhead wires, with the Terminal Drugs store and downtown office buildings behind it. San Francisco Municipal Railway PCC streetcar 1144, signed for Judah, rounds the loop at what appears to be the Transbay Terminal, likely in 1964. October 5, 1964 · Bridge Terminal, Chicago, IL A blue and white diesel locomotive pulls a passenger train on multiple tracks, with a brick building and city skyline in the background. A Nickel Plate Road EMD E7 locomotive, No. 190, pulls a passenger train through a Chicago rail yard, with the Universal Loading & Distributing building in the background. 1965 · Roosevelt Road, Chicago, IL Two diesel locomotives and passenger cars on multiple tracks with city buildings and overpasses in the background. A Chicago Burlington and Quincy F3 locomotive, number 243, pulls a passenger train through a rail yard in Chicago, with another CB&Q unit and freight cars nearby. 1965 · Roosevelt Road, Chicago, IL A silver EMD F3 diesel locomotive with red stripes, bearing the number 99306 and the name 'Denver Zephyr,' leads a train through a snowy yard with other passenger cars on adjacent tracks. A Chicago Burlington and Quincy EMD F3 locomotive, number 99306, pulling the Denver Zephyr train through a snowy rail yard. 1965 · Canal and Roosevelt, Chicago, IL A white bus with a cartoon mural on its side is on a city street, with storefronts and pedestrians in the background. A Chicago Transit Authority Flxible New Look bus with a cartoon advertisement cruises down a city street. December 1, 1965 · Randolph and Wacker, Chicago, IL Two CTA buses, one showing route 100-Bensley and number 6555, are in heavy traffic with a police officer on a car behind them, amidst 1950s automobiles. Two Chicago Transit Authority buses, including #6555 on the Jeffery Express route, navigate a busy street in the late 1950s, surrounded by vintage cars and a police officer directing traffic. 1966 · State and Van Buren, Chicago, IL A gray streamlined diesel locomotive with a CENTRAL herald on its nose and a booster unit behind it pulls a line of express cars along multiple tracks past brick freight houses. New York Central diesel locomotive 400[?] leads a head-end train near Roosevelt Road in Chicago. 1966 · Roosevelt Road, Chicago, IL A black and white photo of a Chicago Transit Authority New Look bus, number 6572, on a city street with trees and cars in the background. A Chicago Transit Authority New Look bus, number 6572, is shown on a city street in 1966, displaying route 81. 1966 · Montrose and Marine Dr, Chicago, IL A green and cream Chicago Transit Authority bus with the number 3077 travels on a street under an elevated train structure, with a 'Terminal Restaurant' and 'Corina Cigars' signs visible nearby. A Chicago Transit Authority New Look bus, number 3077, on route 62 Lindale-29, is seen on a city street with an elevated structure and a 'Corina Cigars' billboard in the background. 1966 · Logan Square, Chicago, IL