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

Summer

1334 photographs
A vintage orange interurban car numbered 270 is parked on an elevated railway platform with a control tower in the background. Chicago South Shore and South Bend Railroad car 270, an Insull-era steel coach, is pictured on an elevated structure with its destination sign reading 'SOUTH SHORE'. c. 1926 to 1947 · 40th, Kenwood, IN A grey, weathered electric railcar with 'LS' on its side and trolley poles on its roof is parked on railroad tracks next to a white building, with a red car partially visible behind it. A weathered Chicago South Shore and South Bend Railroad Master Unit railcar marked 'LS' sits idle on tracks in a yard. c. 1926 to 1956 A black steam locomotive with the number 1385 on its front, emitting thick black smoke, moves along tracks flanked by trees and tall grass on a sunny day. Steam locomotive #1385 blows black smoke as it approaches on a sun-dappled, overgrown private right-of-way in summer. c. 1930 to 2000 A black and white photo shows a trolleybus on a city street with a large crowd of people holding protest signs, one of which reads 'FOSTER AVE FEEDER BUS WED. JUNE 30', marking the last day of trolleybus service on that route. A Chicago Surface Lines trolleybus, number 82 on the Kimball-Leland route, is surrounded by a crowd of protesters holding signs on the last day of service for the Foster Avenue feeder line on June 30, 1936. June 21, 1931 A black and white photo shows a Chicago trolleybus on a city street, with a large crowd of people holding signs in front of it, protesting a bus route change. A Chicago Surface Lines Brill trolleybus, number 1033, on route 82 Kimball Leland, is surrounded by a crowd holding protest signs about a new feeder bus route in the late 1930s. June 21, 1931 · Kimball, Chicago, IL A vintage orange interurban train with the number 1260 on its side and a destination sign reading 'EVANSTON MILMETTE' travels on elevated tracks surrounded by trees on a clear day. Chicago North Shore and Milwaukee Master Unit interurban car 1260, heading to Evanston and Wilmette, on an elevated structure in summer. c. 1940 to 1963 A dark green Pullman troop sleeper car numbered 7271 sits on tracks next to a yellow passenger car under overhead wires, with grass and a brick path in the foreground. A Pullman troop sleeper car, number 7271, is parked in a yard next to a light yellow passenger car, under an overhead wire system on an overcast day. c. 1940 to 1970 A black and white street scene showing a Chicago Surface Lines streetcar numbered 3006 on the front, pulling a second car down a busy city street lined with buildings and pedestrians. Chicago Surface Lines Master Unit streetcar 3006 on route 87 to Macine at State and Van Buren, circa 1935. June 1940 · State and Van Buren, Chicago, IL A black-and-white photo of a Chicago Rapid Transit Company 4000-series rapid transit car, numbered 4085, at an elevated station with a platform and tracks visible. Chicago Rapid Transit Company car 4085, a 4000-series rapid transit car, stopped at an elevated station platform. 1941 · Wells and Randolph, Chicago, IL A black steam locomotive billowing thick black smoke travels on a set of tracks with embankments and utility poles on either side. A steam locomotive emits a large plume of black smoke as it travels along a set of tracks bordered by embankments and utility poles. July 1941 · Roxbury, MA A black-and-white photo of a vintage streetcar numbered 3286 on a city street, with a drugstore and other storefronts visible behind it. Chicago Surface Lines Master Unit streetcar 3286, photographed on a city street with storefronts in the background. 1942 · 78 and Broadway A vintage black and white photo shows a white, wood-bodied electric interurban car numbered 4427 with a navy recruitment ad along its side, sitting on tracks in a grassy area. Chicago Surface Lines interurban car 4427, a Cincinnati Car Master Unit, displays a 'Join the WAVES' recruitment advertisement while stopped in a grassy yard. 1942 · Skokie, IL A black and white photo of a heavily damaged rapid transit car with its front end crumpled, sitting on an elevated track next to another car. A severely damaged Chicago Rapid Transit Company 4000-series rapid transit car after a wreck, seen on an elevated structure. July 1944 · 61 St and Calumet, Chicago, IL A black and white photograph shows a vintage Chicago streetcar on a city street with an elevated railway overhead and a large building in the background. The car is numbered 1412 and displays the route 26-Cottage. Chicago Surface Lines streetcar 1412 on the 26-Cottage route at 26th and Wabash, likely in the late 1930s or early 1940s. 1945 · 26th and Wabash, Chicago, IL A vintage streetcar with the number 3298 and destination Montrose is shown on a city street with overhead wires, passengers visible inside, and a few pedestrians nearby. Chicago Surface Lines Peter Witt streetcar number 3298 heads to Montrose on a summer day in the 1930s or 1940s. 1945 · Montrose and Lincoln, Chicago, IL A vintage black and white photo of Chicago Surface Lines streetcar 3293, a Master Unit, stopped on a cobblestone street with storefronts in the background. Chicago Surface Lines Master Unit streetcar 3293 on a downtown street, likely Montrose and Clark, in the early 1930s. 1945 · Montrose and Clark, Chicago, IL A black and white photo of two vintage streetcars, numbers 604 and 8010, operating on a city street lined with shops and a few automobiles. A Chicago Surface Lines Peter Witt streetcar, number 604, is shown at a street intersection, with a Master Unit car, number 8010, visible in the background. 1945 A black and white photo of a vintage Chicago Surface Lines streetcar numbered 6180 on a city street, with a 1950s sedan and a building in the background. Chicago Surface Lines streetcar 6180, a Master Unit, is pictured on a street, likely in Cicero, Illinois, during the early 1950s. 1946 · Lawrence and Cicero, Cicero, IL A vintage black-and-white photo shows a Chicago Surface Lines streetcar, number 3010, on a city street with 1930s automobiles parked nearby and a brick building in the background. Chicago Surface Lines Master Unit streetcar 3010 on a summer day, likely at 29th and Wallace Streets in Chicago. 1946 · 29th and Wallace, Chicago, IL A black-and-white photo of a 1940s streetcar on a city street with vintage automobiles and storefronts. A Chicago Surface Lines Peter Witt streetcar, number 868, on route 80, navigating a bustling street lined with shops in the 1940s. 1946 A black-and-white photograph of a vintage Chicago streetcar with the number 400, showing a driver inside and the destination sign reading 'LAWRENCE - BROADWAY'. A Chicago Surface Lines Peter Witt streetcar, number 400, on the Lawrence-Broadway route. 1946 · Lawrence and Austin, Chicago, IL A vintage black and white photo of a Chicago Surface Lines bus, number 4[?]2, driving down a street lined with trees and old cars on a sunny day. A Chicago Surface Lines motor bus, number 4[?]2, travels down a tree-lined street in summer, with 1940s automobiles following behind. 1946 · 3 and 73 Rd St. A vintage black-and-white photo of a Chicago Surface Lines streetcar, number 600, with passengers inside, a conductor in the front, and people on the street under a network of overhead wires. A Chicago Surface Lines Master Unit streetcar, number 600, on route 42 to North Western Station, likely in the mid-1930s. 1946 · Milwaukee, WI A black-and-white photo of a vintage streetcar, number 3286, on a city street with storefronts and pedestrians visible. A Chicago Surface Lines Master Unit streetcar, number 3286, operates on a city street in the 1930s or 1940s. 1946 · Montrose and Broadway, Chicago, IL A vintage black and white photo of a streetcar on a city street with an elevated train above it and storefronts along the sidewalk. A Chicago Surface Lines Master Unit streetcar, number 3260, travels along a city street under an elevated rapid transit line. 1946 · 69th and Normal Blvd A black-and-white street scene from the 1930s showing a Chicago Surface Lines streetcar numbered 3260 on the street, with a Chicago Rapid Transit Company elevated car visible on the structure above. A Chicago Surface Lines Master Unit streetcar, number 3260, on a street below an elevated structure carrying a Chicago Rapid Transit Company car, likely at 69th and Normal Boulevard in the late 1930s. 1946 · 69th and Normal Blvd., Chicago, IL A 1940s motor bus from Chicago Surface Lines, fleet number 318, labeled 'Archer Express Cicero-63', is stopped at a bus stop on a sunny day, with American Airlines and Texaco buildings visible in the background. A Chicago Surface Lines bus, number 318 on the Archer Express route to Cicero-63, is shown stopped at a bus stop in 1946 with an airport in the background. 1946 · Cicero and 63rd St., Cicero, IL A black and white photograph of a 1940s-era Chicago Surface Lines bus driving down a tree-lined street, viewed from a three-quarter front angle, with several vintage cars behind it. A Chicago Surface Lines bus operates on a tree-lined residential street in 1946, with a line of vintage automobiles following behind. 1946 · South Park and 73rd St., Chicago, IL A vintage red electric interurban streetcar on a city street, surrounded by 1950s cars, palm trees, and multi-story buildings. A Pacific Electric Railway interurban car, number 1541, known as the 'Long Beach Limited', runs on a street through a city with palm trees and mid-century automobiles. c. 1947 to 1953 A large sign reading 'SOUTH SHORE LINE' with a red train graphic on top, mounted on wooden poles next to a white building and a grassy area where utility poles line the path. A large, vintage 'SOUTH SHORE LINE' sign with a red train graphic stands on a wooden frame beside a white building and a grassy right-of-way. c. 1947 to 1980 A vintage streetcar, number 1675, is shown inside a dimly lit tunnel, with two operators visible in the front cab and the destination sign reading 'DIVISION-CALIFORNIA'. A Chicago Surface Lines Master Unit streetcar, numbered 1675, runs through the Van Buren Tunnel with its 'DIVISION-CALIFORNIA' destination displayed. June 10, 1947 · Van Buren Tunnel A black-and-white photo of a single, old rapid transit car, number 2077, on an elevated track with snow on the ground and city buildings in the background. A Chicago Rapid Transit Company 2000-series rapid transit car, number 2077, on an elevated structure in winter. July 18, 1947 · Market and Madison, Chicago, IL A vintage black-and-white photo of a Chicago Surface Lines streetcar, number 6180, with a trolley pole, running on a city street with cars and a building in the background. Chicago Surface Lines Master Unit streetcar 6180 operates on route 81, viewed from a three-quarter front angle on a summer street. 1948 · Lawrence and Cicero, Chicago, IL A historic black-and-white photo of a Chicago Surface Lines streetcar numbered 0178 on route 81, running on a city street with overhead wires and a building marked 'COMMERCIAL WEST' in the background. Chicago Surface Lines Master Unit streetcar 0178 on route 81, likely on Lawrence Avenue, in the 1930s. 1948 A vintage red streetcar with a curved roof runs on cobblestone tracks past a brick building with storefronts and a yellow car in the background. A red Chicago Surface Lines Master Unit streetcar, number 1619, operates on a city street in the 1940s. 1948 · Van Buren and Marshfield A red and cream vintage streetcar with the number 1769 on the front and route 58 on top, running on tracks down a city street with 1940s cars and buildings. A red and cream Chicago Surface Lines Master Unit streetcar, number 1769, on route 58, travels down a tree-lined street in the mid-1940s. 1948 A vintage black-and-white photo of a CTA bus driving down a street with trolley tracks, past storefronts and parked 1950s cars. A Chicago Transit Authority New Look bus, number 2371 on route 40 Lincoln-Southport, drives down a tree-lined street in Chicago. 1948 · Lincoln and Southport, Chicago, IL Black and white photo of a CTA bus on a city street with overhead wires, an overpass in the background, and vintage cars. A Chicago Transit Authority Flxible bus, number 3[?]1 on route 79 to North Ave. and Marquette, navigates a street corner under a railroad overpass, with a 1940s automobile blurred in motion nearby. 1948 · Montrose and Cicero, Chicago, IL Rear view of a 1950s CTA bus on a city street with old cars, a Sinclair gas station, and a church steeple in the background. A Chicago Transit Authority Flxible bus, number 2363, travels down a street with embedded trolley tracks on a summer day in the 1950s. 1948 · Southport, Chicago, IL A vintage black-and-white photograph of a Chicago Transit Authority bus from the 1950s on a city street, with embedded trolley tracks, classic cars, and a Sinclair gas station in the background. A Chicago Transit Authority bus, number 2358, serves the Lakeview-Ashland route on a street with embedded trolley tracks in the mid-1950s. 1948 · Southport and Diversey, Chicago, IL A red and cream streetcar from the Chicago Surface Lines, numbered 1592, is shown on a city street with a large industrial building and an automobile in the background. A Chicago Surface Lines Master Unit streetcar, number 1592, runs on a city street in the 1930s or 1940s, captured in a three-quarter front view. 1948 · Van Buren and Racine, Chicago, IL Black and white photo of a streetcar on a cobblestone street with an elevated railroad track above it, carrying a steam locomotive. A Chicago Rapid Transit Company streetcar, number 277, on a street under an elevated structure carrying a Chicago and North Western steam locomotive, number 1526. 1948 · Grand and Union, Chicago, IL An orange and black interurban car with the number 261 is stopped at a brick elevated station platform, with a large 'Beatrice Foods Co.' billboard visible on a building in the background. A Chicago Aurora and Elgin interurban car, number 261, is pictured on an elevated structure in Chicago, likely in the 1940s or 1950s. July 1948 · Wilson 18th St, Chicago, IL A vintage orange and maroon interurban railcar, number 1100 of the Chicago South Shore and South Bend Railroad, sits on tracks with overhead wires and trees in the background. The Chicago South Shore and South Bend Railroad's unique Master Unit car, number 1100, is shown in its distinctive orange and maroon livery on a private right-of-way. 1949 · Michigan City, IN A red Chicago Surface Lines streetcar, number 3074, travels down a city street with overhead wires, past a large billboard and older automobiles. Chicago Surface Lines Master Unit streetcar number 3074, running on route 55 to Elston, is captured in motion on a sunny day in the late 1930s. 1949 · 55 and Lawrence, Chicago, IL A black and white photograph of a vintage Chicago Surface Lines streetcar numbered 6180, showing its side and front with a trolley pole raised, parked on a street with cars and a building in the background. Chicago Surface Lines Master Unit streetcar 6180 on route 81, captured in a three-quarter front view on a street in Chicago. 1949 · Lawrence and Cicero, Chicago, IL A vintage black-and-white photo of a Chicago Surface Lines streetcar, number 6178, on a city street with a building labeled 'Commercial Wharf' behind it. Chicago Surface Lines Master Unit streetcar 6178 on a summer day, with the Commercial Wharf building in the background. 1949 · Western, Lincoln, Chicago, IL An orange electric locomotive numbered 11008 with a pantograph, pulling a long line of matching orange boxcars in a railroad yard under overhead wires. Chicago South Shore and South Bend Railroad E-1 electric locomotive 11008 in orange livery, pulling a consist of matching orange freight cars in a yard with overhead wires. 1949 · Michigan City, IN