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

Winter

1089 photographs
A vintage black-and-white photo of a Chicago Surface Lines streetcar numbered 3185, viewed from the front-left on a street with overhead wires and a building in the background. Chicago Surface Lines Master Unit streetcar 3185 is shown in a three-quarter front view on a city street. c. 1930 to 1939 Black-and-white photo of a vintage Superior motor bus, number 519, with 'ILL. C.C. No. 19' on its side, parked on a city street with snow on the ground. An Illinois Central Coach Company motor bus, number 519, at the 87-Vincennes route terminus in Chicago, likely during the 1930s. 1936 · 77th and Vincennes, Chicago, IL A vintage black-and-white photo of a 1936 Chicago Surface Lines motor bus, number 418, on a cobblestone street, showing its front and side with a '95 95-STATE' route sign and a 1936 Illinois license plate. A 1936 Chicago Surface Lines White motor bus, number 418, parked on a cobblestone street with its route sign reading '95 95-STATE'. 1936 · 77th and Vincennes, Chicago, IL A black and white photo of two vintage streetcars on a snowy city street lined with parked cars and large stone buildings. Two Chicago Surface Lines Peter Witt streetcars, numbers 1971 and 1955, are shown on a snow-covered street with parked 1930s automobiles and large stone buildings. 1937 · Fairbanks, Chicago, IL A vintage black-and-white photo showing a streetcar on a wet city street in front of a movie theater, with pedestrians and an elevated train structure in the background. A Chicago Surface Lines Master Unit streetcar, number 3022, heading to Elston, captured in a winter street scene near the Chicago Theater with a marquee advertising 'Love Thy Neighbor'. December 1938 · State and Lake, Chicago, IL A black and white photograph of two vintage streetcars on a dirt road in Chicago; one is numbered 5023 and the other 6163, both with trolley poles and route signs, set against a backdrop of large buildings. Two Chicago Surface Lines streetcars, a Master Unit and a Peter Witt, on an unpaved street in winter. 1942 · State and Randolph, Chicago, IL A vintage black and white photo of a Chicago streetcar, number 1412, on the 26-Cottage route, driving on a street with an elevated train track in the background and a building labeled 'PLYMOUTH' on the right. Chicago Surface Lines streetcar 1412 on the 26-Cottage route, operating on Wabash Avenue under an elevated railway structure. 1945 · 26th Wabash, Chicago, IL A black and white photograph of two Chicago North Shore and Milwaukee interurban cars on a snow-covered street in Milwaukee, with car 3288 in the foreground showing its destination as Montrose. Chicago North Shore and Milwaukee interurban car 3288, a Master Unit, on a Milwaukee street in winter, with another car visible in the background. 1945 · Milwaukee, WI A black-and-white photo of a vintage Chicago Aurora and Elgin interurban car, number 2157, on an elevated track with passengers visible inside; signs indicate routes to Douglas Park, Cicero, and Berwyn. A Chicago Aurora and Elgin interurban car numbered 2157, showing its destination to Douglas Park, Cicero, and Berwyn, on an elevated structure in Chicago. 1945 · Douglas and Polk St., Chicago, IL A black and white photo showing three workers washing a white and dark green bus with the number 1183 and 'Chicago Motor Coach Company' lettering inside a large, windowed garage. Workers wash a Chicago Motor Coach Company GMC TDH-5303 bus, number 1183, inside a large garage. 1946 · Diversey and Keeler A black-and-white photograph of a city street in Chicago with double-decker buses, classic cars, and pedestrians, with a large apartment building in the background. A street scene at the intersection of Sheridan and Foster in Chicago, featuring double-decker and single-decker buses alongside 1940s automobiles. 1946 · Sheridan and Foster, Chicago, IL A black and white photo of a double-decker bus on a city street with pedestrians and old buildings. The bus is marked '51 SHERIDAN RD.' and 'ADAMS' with the number 114. A double-decker Chicago Motor Coach Company bus, number 114, operating on route 51 Sheridan Road in downtown Chicago during the 1940s. 1946 A black and white photo of a vintage motor bus on a city street with tall buildings in the background. A passenger is boarding, and other cars are visible. A Chicago Surface Lines motor bus, number 1613, on route 41 to Clybourn-Belmont, navigating city streets in winter. 1946 · Orleans and Merchandise Mart, Chicago, IL A vintage black and white photograph of a Master Unit streetcar with fleet number 400, displaying a destination sign for LAWRENCE - BROADWAY and a 'STEP IN SAVE STEPS' sign on its front, parked on a snowy street. A Chicago Surface Lines Master Unit streetcar, number 400, is shown on a winter day with its destination sign reading "LAWRENCE - BROADWAY". 1946 · Lawrence and Austin, Chicago, IL A black-and-white photo shows a vintage double-decker bus on a wide city street, with pedestrians on the sidewalks and multi-story buildings lining the road. The bus displays route 51 Sheridan Road and destination Adams. A Chicago Surface Lines double-decker bus, number 114, runs on Sheridan Road in Chicago under overcast skies, likely in the late 1930s or 1940s. 1946 · Sheridan and Wilson, Chicago, IL A black and white photo shows a side view of a white and dark-colored bus with 'CHICAGO MOTOR COACH COMPANY' lettered on its side, driving on a street in winter with bare trees and a tall column monument in the background. A Chicago Motor Coach Company bus, number 1810, on a winter street with the Logan Square Monument in the background. 1946 · Logan Square, Chicago, IL A black and white photo of a vintage Chicago Motor Coach Company bus, number 577, parked on a city street with a person in a coat nearby. A Chicago Motor Coach Company Flxible bus, number 577, is shown on a city street, likely in the late 1940s or early 1950s, with its 'The Boulevard Route' lettering visible. c. 1947 to 1953 Black-and-white photo of a streamlined streetcar with its trolley pole raised, on a snowy street in front of a brick factory lettered MACHINE CO., with overhead wires above. Chicago Transit Authority PCC streetcar 406[?] signed for route 20 Monroe-Dearborn, likely at Madison Street and Fifth Avenue on Chicago's West Side, in winter. c. 1948 to 1953 · Madison and 5th Av., Chicago, IL A green and cream trolleybus with the number 9501 and route 12 to Roosevelt and Wabash is parked at a snowy street corner next to a brick building with a sign for 'Red's.' A Chicago Transit Authority Flxible trolleybus, number 9501, on route 12 to Roosevelt and Wabash, stopped at a snowy bus stop. c. 1948 to 1973 A black and white photo of a Chicago Transit Authority motor bus, number 1787, showing its front and side with route signs and advertisements, parked on a wet street with a house in the background. Chicago Transit Authority bus number 1787, a Flxible New Look, on the 82 Kimball-Foster route in a winter scene. 1948 · Kedzie and Foster, Chicago, IL A vintage black-and-white photo of a Chicago streetcar numbered 507 parked on a snowy street, with a large circular billboard above it advertising Blue Ribbon Beer. Chicago Surface Lines Master Unit streetcar number 507, likely in the early 1930s, standing on a snowy street beside a large Blue Ribbon Beer billboard. 1948 · Clark and Southport, Chicago, IL A vintage red streetcar with a destination arch is stopped on a snow-dusted street with bare trees in the background. Two people are near the car. A red Chicago Surface Lines Master Unit streetcar, fleet number 6[?]7, is shown on a snowy Chicago street, likely at the Bryn Mawr and Pulaski intersection. 1948 · Bryn Mawr and Pulaski, Chicago, IL A vintage Chicago Transit Authority motor bus is parked on a street near a gazebo with bare trees in the background. A Chicago Transit Authority New Look bus from the 1960s is posed on a street near a gazebo in winter. 1948 A vintage black and white photograph shows a CSL streetcar, number 211, on a cobblestone street with overhead wires, next to a pre-war delivery truck. A Chicago Surface Lines Master Unit streetcar, number 211, is pictured on a winter day in the 1930s, with a vintage delivery truck nearby. December 31, 1948 A vintage green and cream Chicago Motor Coach Company bus, number 1165, is parked on a street with bare trees in the background. The destination sign reads '26 Jackson Via Harmon'. Chicago Motor Coach Company bus 1165, a GM New Look, is shown on route 26 Jackson Via Harmon in a winter setting. 1949 · Columbus Park, Chicago, IL A red and cream Chicago Surface Lines streetcar, number 328, is stopped on a snowy street with bare trees in the background, as a few people wait to board. A Chicago Surface Lines Master Unit streetcar, number 328, is shown in winter at the intersection of Pulaski and Bryn Mawr. 1949 · Pulaski and Bryn Mawr, Chicago, IL A red and cream streetcar numbered 1046 is shown from a three-quarter front view, running on a street with bare trees and a gasoline pump in the background. A Chicago Surface Lines Birney streetcar, number 1046, captured in winter on a street-running route. 1949 · Southport and Clark, Chicago, IL A black steam locomotive with the number 1984 on its front, emitting white smoke, is shown pulling a long line of freight cars along multiple tracks next to a station platform under a blue sky with bare trees nearby. A Chicago and North Western steam locomotive, number 1984, pulls a long freight train past a station platform on a clear winter day in 1949. 1949 · Hinsdale, IL Two diesel locomotives, one black and yellow and the other red and blue, are coupled together on snow-covered tracks next to a railroad crossing signal. The Belt Railway Company of Chicago's SW1200 locomotives 533 and 534 are stopped at a snowy grade crossing. c. 1950 to 1980 A yellow and orange Rock Island diesel locomotive, number 676, is at a station platform pulling silver passenger cars under an arched roof with skylights. A Rock Island F7 diesel locomotive, number 676, is shown at a station platform pulling a consist of Hi-Line passenger cars under an arched roof during winter. c. 1950 to 1970 A red and green streetcar and a green and cream bus are on a city street with tall buildings, neon signs for 'SPIEGEL' and 'the COTTON shop', and mid-1950s cars. A woman in a coat is crossing the street. A Chicago Transit Authority Birney streetcar and a New Look bus share the street in downtown Chicago, likely on State Street, in the mid-1950s. 1950 · State Madison, Chicago, IL A vintage black-and-white photo of a Chicago Surface Lines streetcar numbered 177, with an elevated railroad bridge labeled 'Englewood Union' behind it, and parked cars nearby. A Chicago Surface Lines Master Unit streetcar, number 177, on a street under the Englewood Union Station bridge. 1950 · 63rd and State, Chicago, IL A vintage black-and-white photo of a streetcar numbered 127 running on a city street under a railway bridge marked 'Englewood Union'. A Chicago Surface Lines Master Unit streetcar, number 127, on a Chicago street near the Englewood Union Station underpass. 1950 · 63rd and State, Chicago, IL Two red and cream streetcars with numbers 610 and 501 are parked in a brick carbarn; the front of car 610 shows a destination sign reading 'ASHLAND AV'. Two Chicago Surface Lines Master Unit streetcars, numbered 610 and 501, are parked side by side in a carbarn with overhead wires visible above. 1951 · 96th and Ashland A green and cream streetcar numbered 4095 travels down a slushy city street past brick warehouses with The Fair billboards, while a red and green train passes on an elevated structure at right. Chicago Transit Authority PCC streetcar 4095 heads along State Street near 15th Street in winter, with The Fair billboards and an elevated train behind. 1951 · 15th and State, Chicago, IL A red and cream interurban car, number 1766, is stopped at a railroad crossing under a large bridge with the words 'Chicago and North Western System' on it; the street sign reads 'Pine Av' and the car's destination sign reads 'LAKE'. Chicago North Shore and Milwaukee interurban car 1766 at a grade crossing under a Chicago and North Western Railway bridge on a winter day. 1951 · Lake and Pine, Chicago, IL A vintage red streetcar with the number 357 and destination 'California + Roscoe' is shown on a snowy street, with a driver visible in the cab and overhead wires above. A red Chicago Surface Lines Master Unit streetcar, number 357, displays its California + Roscoe destination on a winter day. 1951 · California and Roscoe, CA A vintage red and cream streetcar with the number 6296 and route 4 sign is moving down a street with overhead wires and a building labeled 'GUARDIT' in the background. A red Chicago Surface Lines Birney streetcar, number 6296, on route 4 to Cottage Grove 65, is seen on a street with a 'GUARDIT' building in the background. 1951 · Cottage Grove and 96th St., Chicago, IL A red and cream interurban car with the number 505 on its side, labeled 'MILWAUKEE' on its front, is shown on a snowy street with passengers visible through its windows, in front of a Tudor-style building. A Milwaukee Road Master Unit interurban car, number 505, in orange and cream livery, stands on a snow-dusted street with passengers on board. January 1951 · Logan Blvd, Milwaukee, WI A vintage electric work car with the number W 205 on its front, parked on a snow-covered track in a rail yard with overhead wires and other cars in the background. A Chicago Surface Lines electric work car, number W 205, stands in a snow-covered yard, its dual control cabs and flatcar body clearly visible under overhead wires. January 1951 · 77th and Vincennes, Chicago, IL A green and cream streetcar with snow on its roof travels toward the camera on a slushy street lined with bare trees and snow-covered lawns, with another streetcar farther back. Chicago Transit Authority PCC streetcar 7154, signed for route 22 Vincennes-80th, on snowy Clark Street, likely near Chase Avenue. 1952 · Clark and Chase, Chicago, IL A black and white photo of a Chicago Transit Authority trolleybus, number 9563, on route 86 NARRAGANSETT, driving down a street with overhead wires and a building displaying ads for Jacob Loibl and City Club Beer. A Chicago Transit Authority trolleybus, number 9563, on route 86 NARRAGANSETT, captured on a winter day with overhead wires and period advertisements in the background. 1952 · 86 and Narragansett A vintage black-and-white photo of a Chicago Transit Authority bus, number 1327, with 'The Boulevard Route' written on its side and 'HARLEM 152 ADDISON' on its front sign, parked near a brick building. A Chicago Transit Authority GM New Look bus, number 1327, in its 'Boulevard Route' livery, parked on a winter day. 1952 · Keeler and Diversey, Chicago, IL A black and white photo showing a line of dark-colored buses inside a garage with striped warning markings on the door; one bus has the number 1320 and a 'NOT IN SERVICE' sign; a man in overalls stands to the right. A Chicago Transit Authority GM New Look bus numbered 1320, marked 'NOT IN SERVICE', is parked inside a garage with other buses, as a man in work clothes stands in the doorway. 1952 A black and white photo of a vintage Chicago Surface Lines motor bus, number 1327, parked on a city street with a destination sign reading 'Harlem 152 Addison' and an advertisement for Braumeister Beer on the front. A Chicago Surface Lines motor bus, number 1327, is parked on a city street, displaying 'Harlem 152 Addison' on its destination sign and 'The Boulevard Route' along its side. 1952 · Diversey and Keeler, Chicago, IL An elevated view of a city street in winter with two vintage streetcars in the foreground, one red and one green, surrounded by cars and brick buildings with signs. Two Chicago Surface Lines streetcars, a Master Unit and a PCC, pass on a city street lined with vintage storefronts in the late 1940s. December 1952 · 63rd and Harvard, Chicago, IL A dark green and orange interurban train with the number 176 is stopped at a small station platform in a bare-treed winter scene, with a man standing nearby. North Shore Line interurban car 176 at the Wilmette station in winter. 1953 · Wilmette, IL A green and cream streetcar rounds a snowy street corner under overhead wires, next to a brick tavern and a painted Drewrys Beer sign. Chicago Transit Authority PCC streetcar 40[?]6 on route 4 in the snow at 115th and St. Lawrence, Chicago. 1953 · 115th and St. Lawrence, Chicago, IL