Flag Stop 4,614 transit photos from Chicago and beyond, mostly 1940s–2000s
Seasons

Winter

1089 photographs
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 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 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 red and green interurban car with the number 747 and a sign reading 'Skokie Valley Route Chicago-Limited' is stopped on a snow-covered track with overhead wires and utility poles in the background. A Chicago North Shore and Milwaukee Master Unit interurban car, number 747, on the Skokie Valley Route in a snowy setting. 1961 · Kenosha, WI A black and orange Indiana Harbor Belt diesel locomotive, number 3802, pulls a freight train with Southern Pacific and ACF Industries cars on a snowy day. An Indiana Harbor Belt GP38-2 locomotive, number 3802, leads a freight train through a snowy landscape, with Southern Pacific and ACF Industries freight cars in tow. January 1961 · Park and Lincoln, Dolton, 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 white city bus with the number 8713 and 'METRO Transit' on its side, driving down a street with a yellow taxicab in the foreground and a large building in the background. A white Metropolitan Transit Authority bus, number 8713, in Oklahoma City, displaying advertisements for 'Ken Boyer Bail Bonds' and 'Project Exile' while driving on a city street. February 1961 · Oklahoma City, OK 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 Two vintage green and cream Chicago Transit Authority buses are parked on a wet street next to a brick wall, with overhead wires visible in the background. Two Chicago Transit Authority Flxible New Look buses, numbered 1620 and 1700, are parked on a wet street in Chicago, displaying route 16 Lake-Austin. February 4, 1962 · North and Cicero, Cicero, 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 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 red and black interurban train on a snowy city street, with vintage cars and tall buildings in the background. A Chicago North Shore and Milwaukee interurban car, number 715, travels on a snow-covered street in Milwaukee, Wisconsin, surrounded by 1950s automobiles. January 20, 1963 · 6th and Clybourn, Milwaukee, WI Three dark gray New York Central diesel locomotives with a shark-shaped nose and white stripes pull a long line of boxcars along the top of a brushy embankment under a blue sky. A New York Central freight led by three gray diesel units, the lead one numbered 38[?][?], climbs an embankment, likely near Avon Yard, Indiana. February 1963 · Avon Yards, IN A silver and red Chicago Burlington and Quincy F7 diesel locomotive numbered 9991 pulls a line of freight cars past a brick signal tower with a sign reading 'DUPLA NVILLE' under an overcast sky. Chicago Burlington and Quincy EMD F7 diesel locomotive 9991 leads a freight train past the DuPlainville signal tower on a winter day. 1965 · Dupainville, 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 A green and cream Chicago Transit Authority bus with the number 5231 on its front bumper is driving on a city street, with other cars and bare trees in the background. A Chicago Transit Authority Flxible New Look bus, number 5231, operates on route 84 Caldwell-Central on a wintry, overcast day. December 31, 1965 Two locomotives, one Southern Pacific and one Louisville and Nashville, pull a line of freight cars through a yard with mountains in the distance. Two EMD GP40 diesel locomotives, one from Southern Pacific and one from Louisville and Nashville, lead a freight train through a yard with snow-capped mountains in the background. c. 1966 to 1970 · Colton, CA A black diesel locomotive with a bright headlight and the number 4019 on its front is stopped at a grade crossing on a snowy evening, with a station building and a street sign that reads 'SPRINGFIELD' in the background. An Illinois Central F8A diesel locomotive, number 4019, is captured at dusk pulling a passenger train through a snowy grade crossing in Springfield, Illinois. 1966 · Springfield, IL A red and silver Santa Fe diesel locomotive, number 352, sits on snowy tracks at night, its headlights on and the 'Santa Fe' name visible on its side. A Santa Fe SD24 diesel locomotive, number 352, is captured at night in a snowy yard, showcasing the iconic Warbonnet livery. 1966 · Joliet, IL A vintage Chicago Transit Authority bus on a snow-covered street, with bare trees and parked cars lining the road. A Chicago Transit Authority Flxible New Look bus, number 159, operates on route 152 Higgins-Pulaski on a snowy winter street. 1966 · Levitt A vintage trolleybus covered in snow and ice, parked on a snowy street with snow-covered buildings in the background. A Chicago Transit Authority trolleybus, number 4550, covered in snow and ice on a winter day. 1967 · State and 66, Chicago, IL A black and white photo of a CTA bus driving down a snow-covered street with buildings and pedestrians in the background. A Chicago Transit Authority New Look bus, number 5571, navigates a snow-covered street in the 1960s. 1967 · Ashland and Addison, Chicago, IL A vintage Chicago Transit Authority bus, number 483, parked in the snow with a 'Shuttle Service' sign on its roof and advertisements on its body. A Chicago Transit Authority Flxible bus, number 483, in winter livery with snow, marked for Route 67 Shuttle Service. 1967 A green and cream CTA bus drives down a busy city street decorated for Christmas, with many cars and people on the sidewalks. A Chicago Transit Authority New Look bus, number 5555, operates on a festive, crowded State Street during the winter holidays, surrounded by cars, taxis, and pedestrians. January 24, 1967 · State and Van Buren, Chicago, IL A green and white CTA bus driving down a crowded city street lined with decorated lampposts and vintage cars, with pedestrians on the sidewalk. A Chicago Transit Authority Flxible New Look bus, number 5855, operates on the 36th & Morgan route through a busy downtown street during the winter holidays. January 24, 1967 · 36th and VAN BUREN, Chicago, IL A high-angle view of a Chicago street in winter, featuring a green and white CTA bus with the number 3095 on its front, surrounded by other vintage cars and buses, with festive Christmas decorations on the lampposts. A Chicago Transit Authority Flxible New Look bus, number 3095, is seen on a busy street during the winter holiday season, with Christmas decorations lining the street and other buses and cars in traffic. January 24, 1967 · Van Buren and State, Chicago, IL Two vintage CTA buses in a snowy Chicago street scene with several people and other vehicles in the background. Two Chicago Transit Authority New Look buses, numbers 872? and 5081, are parked on a snow-covered street during a winter day in Chicago. January 27, 1967 · Granville, Chicago, IL A winter scene with two snow-covered Chicago Transit Authority buses on a city street, one showing destination Kedzie-Foster and number 2110, with billboards and a snow-covered car nearby. Chicago Transit Authority buses 2110 and 5081 are stranded on a snow-covered street at the corner of Western and Granville, with the Comet sign visible in the background. January 27, 1967 · Western and Granville, Chicago, IL A diesel locomotive numbered 260, painted in Chicago Burlington and Quincy livery, leads a freight train through a snow-covered scene next to a blue Ford pickup truck. A Chicago Burlington and Quincy EMD F7 locomotive, number 260, pulls a line of freight cars through a snowy yard in Mendota, Illinois, as a blue Ford pickup waits at the crossing. January 27, 1967 · Mendota, IL A black and white photo of a CTA trolleybus on a snowy street in Cicero, Illinois, with people walking nearby and storefronts lining the street. A Chicago Transit Authority trolleybus, number 5201, navigates a snow-covered street in Cicero, Illinois, with pedestrians crossing in the foreground. January 30, 1967 · Cicero and Milwaukee, Chicago, IL A line of freight cars on a railroad track, including two red Western Pacific boxcars and a yellow TTX flatcar, with bare trees and overhead wires in the background. A Western Pacific freight train with 40-foot wood boxcars and a TTX bulkhead flatcar on a clear winter day. December 8, 1967 · Lincoln Ave, Dolton, IL A black and white photo of a Chicago Transit Authority bus, number 5533, on the 62 Archer-Harlem route, driving through a crowded city street lined with decorated trees and tall buildings. A Chicago Transit Authority Flxible New Look bus, number 5533, on route 62 Archer-Harlem, navigates a busy downtown street at State & Van Buren, decorated for the holidays in the early 1970s. 1968 · State and Van Buren, Chicago, IL A side view of a Chicago Transit Authority New Look bus, number 5172, parked in a lot with snow on the ground, showing its dark green and cream paint and the CTA logo. Chicago Transit Authority New Look bus #5172, painted in dark green and cream livery, is parked in a snow-dusted yard on a clear winter day. February 1968 · Elston and Bryn Mawr, Chicago, IL Two burned-out CTA buses, one numbered 3153 and the other 5481, are shown front-on in a wrecked state on a street with debris around them. Two burned-out Chicago Transit Authority Flxible New Look buses, numbered 3153 and 5481, sit in a pile of wreckage on a Chicago street. 1969 · Kedzie and Van Buren, Chicago, IL Two heavily damaged and burned-out buses with fleet numbers 3153 and 5481, showing signs of being in a scrapyard. Two burned-out Chicago Transit Authority Flxible New Look buses, fleet numbers 3153 and 5481, sit in a scrapyard. 1969 · Kedzie Two heavily damaged buses, numbered 3153 and 5481, stand side by side in a wrecked condition in a yard, with one showing the route number 876 on its destination sign. Two burned-out Chicago Transit Authority buses, fleet numbers 3153 and 5481, sit in a scrapyard after a fire or accident. 1969 · Kedzie Jackson A black and white photo shows the heavily damaged front of a bus with the number 3150, its roof torn off and interior exposed, parked next to a brick building. The burned-out remains of Chicago Transit Authority bus 3150, a GM New Look, lie on a city street. 1969 · Kedzie and Jackson, Chicago, IL A wrecked and burned bus with the number 3150 on its front, sitting on a city street next to a brick building, with another bus visible in the background. A burned-out Chicago Transit Authority Flxible New Look bus, number 3150, is photographed on a city street after a wreck. 1969 · Kedzie Van Buren