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

Winter

1089 photographs
A green and yellow Chicago and North Western diesel locomotive, number 6500, sits on tracks in a rail yard with snow on the ground. Chicago and North Western GP9 diesel locomotive #6500 in green and yellow livery, photographed in a rail yard during winter. c. 1954 to 1972 A red and green streamlined interurban train car with the number 741 on the front, moving along a snow-lined city street with overhead wires and a 'Schlitz' billboard in the background. An Electroliner interurban car, number 741, of the Chicago North Shore and Milwaukee, travels along a snowy street in Milwaukee, Wisconsin, likely on N. 6th St. & W. St. Paul. 1954 · N. 6th St. and W. St. Paul, Milwaukee, WI A long, streamlined electric train with a blue and red paint scheme and a silver upper body stands on railroad tracks in a snowy, open field under an overcast sky. A Chicago North Shore and Milwaukee Silverliner interurban car in its distinctive blue and red livery stands on a snowy right-of-way. 1954 · Lake Bluff, IL Green and orange interurban train on a street with bare trees, showing destination 'CHICAGO-EXPRESS SHORE LINE ROUTE' and number 164. A Chicago North Shore and Milwaukee interurban train, car 164, in green and orange livery, runs on Kenilworth Avenue in winter 1954, with bare trees lining the street. 1954 · Kenilworth Ave A vintage red streetcar numbered 688 travels across a metal truss bridge, with its destination sign showing 63RD-STONY, and cars following behind under bright sunlight. A red Chicago Surface Lines Peter Witt streetcar, number 688, crosses a truss bridge on a sunny day, its destination sign reading '63RD-STONY'. February 22, 1954 · Halsted and Kinzie, Chicago, IL A red and cream streetcar with the number 317 on its front travels down a cobblestone street lined with 1950s cars and buildings with signs reading 'Romano Drugs' and 'Coca-Cola'. A Chicago Surface Lines Master Unit streetcar, number 317, on a city street lined with parked automobiles and storefronts, including Romano Drugs, in the early 1950s. February 22, 1954 · Grand, Halsted and Milwaukee, Chicago, IL A red and cream CA&E interurban car numbered 171 is stopped at a rural station platform with overhead wires, a person walking nearby, and a car parked in the background. CA&E interurban car 171, a wood-body electric car, is pictured at the Elmhurst station on a wet, overcast day. 1955 · York Rd., Elmhurst, IL A train crosses a metal trestle bridge over a snowy, brushy valley on a cloudy winter day. A train crosses a snow-covered trestle bridge in winter. 1955 · McCormick Blvd., Chicago, IL A black and white photo of several CTA trolleybuses lined up on a street in winter; the lead bus, number 9418, has its destination sign reading '47 47th - LAKE PARK' and a passenger is boarding. A line of Chicago Transit Authority Flxible trolleybuses, including number 9418 on route 47 to Lake Park, are stopped on a winter street. 1955 · 47th and Archer, Chicago, IL A black and white photo shows a Chicago Transit Authority bus driving on a wide highway with other cars; the surrounding trees are bare, indicating winter. A Chicago Transit Authority New Look bus, number 6177, travels on a multi-lane highway alongside 1950s automobiles on a winter day. 1955 · Outer Drive and North Av., Chicago, IL Front view of a vintage Chicago Transit Authority bus on a snowy street, with a 1950s car parked to the side and bare trees in the background. A Chicago Transit Authority Flxible New Look bus, number 1301, operates on route 76 - Diversey during a snowy winter day, with a snow-covered 1950s Chevrolet parked nearby. 1955 A vintage black and white photo shows a CTA bus on a snow-covered street with a 1950s car parked nearby and bare trees lining the road. A Chicago Transit Authority Flxible New Look bus, number 1301, on route 76 Diversey, navigating a snowy street. 1955 · Diversey and Springfield, Chicago, IL A yellow streetcar numbered 1399 runs toward the camera on double track in a dirt median, with tall utility poles, palm trees and trimmed hedges along a wide boulevard. Los Angeles Transit Lines car 1399 on route 5 runs along a median right-of-way, likely near Inglewood Cemetery. January 1955 · Inglewood Cemetery, Los Angeles, CA A yellow streetcar with the number 1399 and route 5 sign travels on embedded tracks beside a road with utility poles and palm trees. A Los Angeles Metropolitan Transit Authority PCC streetcar, number 1399, operates on a sunny day along a palm-lined street in the 1950s. January 1955 A vintage interurban car running on an elevated railway track, with city buildings and water towers in the background. A Chicago North Shore and Milwaukee Master Unit car, number 324, on an elevated track in Chicago. January 1955 · Garfield Racine Ave, Chicago, IL A yellow and green streetcar numbered 1307, with its trolley pole raised, stands beside a raised concrete safety island on a wet street under a stormy sky, with palm trees, a HUDSON sign and 1950s cars lining the road behind it. Streetcar 1307 waits at a safety island on a rain-soaked street lined with palm trees, likely at 48th and Crenshaw Boulevard in Los Angeles. January 1, 1955 · 48th and Crenshaw Bl., Los Angeles, CA A vintage green and orange streetcar with the number 1307 is stopped on a rain-slicked street, with overhead wires and a 'HUDSON' business sign visible in the background. A Los Angeles Metropolitan Transit Authority PCC streetcar, number 1307, navigates a wet street under overcast skies. January 1, 1955 · 48th and Crenshaw Blvd, Los Angeles, CA A red and yellow electric car with a trolley pole crosses a long wooden and steel trestle high above a street, with power lines and a blue sky with clouds above. A red Pacific Electric car crosses the Fletcher Drive Trestle in Los Angeles. February 25, 1955 · Fletcher Drive Trestle, Los Angeles, CA A red streetcar with a trolley pole crosses a long trestle with timber and steel spans against a blue sky. Utility poles and wires stand above it, a stucco building is at lower left, and a street with cars is at lower right. A Pacific Electric Railway PCC streetcar crosses the Fletcher Drive Trestle above a city street. February 25, 1955 · Fletcher Drive Trestle, Los Angeles, CA A green and cream Chicago Surface Lines bus, number 5070, drives down a street lined with 1950s cars, with store signs and bare trees in the background. A Chicago Surface Lines motor bus, number 5070, is seen on route 44th Western-Leland, navigating a street with visible streetcar tracks, surrounded by vintage 1950s automobiles. December 11, 1955 · Farragut, Chicago, IL A black and white photograph of a Chicago Transit Authority Flxible bus numbered 7206 on a city street in winter, with vintage cars and a building labeled 'Air Line Pilots Association Int'l' in the background. CTA Flxible motor bus number 7206 on route 6 CICERO - 55TH, photographed at the intersection of 55th and Cicero in Chicago during the winter, likely in the 1960s. 1956 · 55th and Cicero, Chicago, IL Front view of a dark-colored CTA bus with the number 2603 and route 49 A Western-79 displayed, stopped at an intersection with a stop sign and a street sign for W 119th St visible. A Chicago Transit Authority GM New Look bus, number 2603, on route 49 A Western-79 at the intersection of 119th Street and Western Avenue on an overcast winter day. 1956 · 119th and Western, Chicago, IL A black and white photo of a Chicago Transit Authority bus turning at a street intersection with a stop sign and a street sign for 119th Street visible. A Chicago Transit Authority Flxible New Look bus, number 2603, on route 49A Western at 119th Street on an overcast winter day. 1956 · 49A and 119th St Two stripped green-and-cream streetcars with their windows removed sit among scrap metal behind a black Frisco gondola and rail tracks, with six smokestacks against an overcast sky. Stripped PCC streetcars, likely of the Chicago Transit Authority and including car 706[?], stand behind St. Louis-San Francisco Railway gondola 61[...]496, likely in St. Louis. February 27, 1956 · St. Louis Two green and cream interurban cars, numbered 7210 and 7201, sit on tracks in a gravel yard with a clear sky and leafless trees in the background. Two Chicago North Shore and Milwaukee Master Unit interurban cars, numbered 7210 and 7201, are parked in a yard in 1957. 1957 · 77th and Vincennes, Chicago, IL A black and yellow Soo Line locomotive numbered 501 is parked in a snowy rail yard with multiple tracks and industrial buildings in the background. Soo Line 501, an EMD SD24 locomotive, stands in a snow-covered yard. c. 1958 to 1970 A single-unit, streamlined railcar with a teal, orange, and silver paint scheme is shown on railroad tracks next to a snow-covered embankment and bare trees in the winter. A Chicago South Shore and South Bend Railroad Budd-built doodlebug in its distinctive teal and orange livery travels along a private right-of-way in winter. 1958 A three-quarter front view of a dark green and white CTA motor bus with number 1787 on its side and front, showing a '82 KIMBALL-FOSTER' destination sign and vintage advertisements on its bumper and side. CTA New Look bus number 1787, assigned to route 82 Kimball-Foster, is parked on a winter street. c. 1959 to 1964 A side-view of a Chicago Transit Authority motor bus, numbered 500, painted in green and white, parked on a snow-covered lot with bare trees in the background. Chicago Transit Authority bus number 500, a GM New Look model, sits in a snowy yard during its service years in the 1960s. c. 1959 to 1970 Front view of a vintage city bus driving on a snow-covered street, with classic cars and bare trees in the background. A Chicago Transit Authority Flxible New Look bus, number 610, on route 24 during a snowstorm, surrounded by 1950s automobiles. c. 1959 to 1968 A green and orange streamlined electric train, labeled Electroliner and North Shore Line, stands at an elevated station platform with snow on the ground. An Electroliner train from the Chicago North Shore and Milwaukee, numbered 801, is pictured at a terminal during winter. 1959 · Terminal, Milwaukee, WI A black and white photo shows a CTA trolleybus with the number 9418 and route 47 to Lake Park, stopped on a street with a trolley pole raised, with another CTA bus nearby and a person boarding. A Chicago Transit Authority Flxible trolleybus, No. 9418, on route 47 to Lake Park, stands on a street with a CTA motor bus in the background. 1959 · 47th and Archer, Chicago, IL A vintage Chicago Transit Authority bus numbered 72 is driving on a city street, surrounded by 1960s-era cars and a large stone building in the background. A Chicago Transit Authority New Look bus numbered 72 is shown in street traffic at the corner of Monroe and Michigan in downtown Chicago. December 1959 · Monroe and Michigan, Chicago, IL A green and cream motor bus, number 571, drives down a city street with snow on the sidewalks and classic cars parked in the background. A Chicago Transit Authority Flxible New Look bus, number 571, is captured on a city street in winter. December 1959 · Michigan and Harrison, Chicago, IL Side view of an Illinois Central diesel locomotive numbered 1500 in a snow-dusted rail yard, with other locomotives behind it. Illinois Central SW1200 locomotive 1500 sits in a snowy yard, with another SW1200 and a Union Pacific GP9 in the background. c. 1960 to 1970 A yellow and gray Union Pacific diesel locomotive, number 1247, is sitting on tracks in a yard, with a second locomotive coupled behind it. A Union Pacific SW1200 diesel locomotive, number 1247, is seen in a rail yard on an overcast day. c. 1960 to 1990 Side view of a green and yellow Chicago and North Western diesel locomotive numbered 6500, parked on tracks in a snowy yard with a red and white truck in the background. A Chicago and North Western EMD SD24 diesel locomotive, number 6500, in green and yellow livery, stands in a snowy yard. c. 1960 to 1972 A vintage dark green and red interurban car runs on streetcar tracks down a tree-lined street with a church steeple in the background on a cloudy winter day. A North Shore Line Master Unit interurban car, number 749, on a winter street in Milwaukee in 1960. 1960 · 5th St., Milwaukee, WI A side view of a yellow Union Pacific diesel locomotive numbered 9679, standing on tracks in a snowy yard next to another diesel locomotive with the reporting mark SX. A Union Pacific SD70M locomotive, number 9679, stands in a snow-covered yard alongside a second locomotive, with snow blanketing the ground and equipment. January 1960 · Lake and Mannheim, Melrose Park, IL A black and white photo of a mid-1950s Chicago bus driving down a snowy street lined with parked cars and bare trees. A Chicago Transit Authority New Look bus, number 1242, travels down a snow-covered street in the mid-1950s. February 10, 1960 · Cicero and Addison, Chicago, IL Black and white photo of a line of buses on a snow-covered city street, with one bus in the foreground showing the number 1242 and a Braumeister ad. A Chicago Transit Authority New Look bus, number 1242, navigates a snow-covered street, with a second CTA bus following behind. February 10, 1960 · Addison and Cicero, Chicago, IL A black and white photo of a Chicago Transit Authority bus number 1242 driving down a snow-covered street lined with parked cars and bare trees. A Chicago Transit Authority New Look bus, number 1242, navigates a snow-covered street at Addison and Cicero in Chicago during the winter. February 10, 1960 · Addison and Cicero, Chicago, IL A black and white nighttime photograph of a CTA bus numbered 5288 with destination sign reading 'MILWAUKEE LIMITED MILWAUKEE - DEVON', as passengers board from a sidewalk. A Chicago Transit Authority bus numbered 5288 at a stop on the Milwaukee Limited route, with passengers boarding at night. December 5, 1960 · Logan Square, Chicago, IL A black and white photo of a 1960s-era CTA bus driving down a snow-covered street lined with parked cars and bare trees. A Chicago Transit Authority Flxible New Look bus, number 1216, runs route 76 Diversey-Harlem on a snowy city street in the 1960s. c. 1961 to 1970 Two green and white Chicago Transit Authority buses from the 1940s or 1950s, numbered 2700, driving down a tree-lined street in winter, with snow on the ground. Two Chicago Transit Authority Flxible motor buses, number 2700, running on route 79-Western in a winter street scene. 1961 · 79th and Brandon, IL A light green and dark green streetcar with a trolley pole runs along a street beneath overhead wires, with gas holders, a Tacos Burritos sign and a house with Christmas decorations behind it. Los Angeles Metropolitan Transit Authority PCC streetcar 3163 on the P line, signed for East First Street, likely in Los Angeles around 1958 to 1963. 1961 · First Nr Center, Los Angeles, CA A vintage Chicago Transit Authority bus, number 1612, painted in cream and green livery, is stopped on a city street under an overcast sky with bare trees, with a Standard gas station sign in the background. Chicago Transit Authority New Look bus number 1612, likely photographed in the 1960s, operating on route 6 to Lake-Austin on a winter day. 1961 Nighttime street scene with a CTA bus on State Street in Chicago, surrounded by holiday lights, pedestrians, and other traffic. A CTA Flxible New Look bus, number 5968, on route 36 119 MORGAN, navigates a festively lit State Street at night in the mid-1960s. 1961 · State and Van Buren, Chicago, IL