Flag Stop 4,614 transit photos from Chicago and beyond, mostly 1940s–2000s
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1334 photographs
A black and white photo shows a CTA bus on a city street at dusk, surrounded by parked cars and pedestrians, with large glowing signs for shops like Sears and Bond's above. A Chicago Transit Authority New Look bus, number 638, on route 8 Halsted, moves down a busy street at dusk, flanked by vintage automobiles and illuminated storefronts. 1951 · 64th St. A vintage streetcar and a bus on a wide Chicago street lined with tall buildings and 1940s cars. A Chicago Surface Lines Peter Witt streetcar, number 629, on a downtown street in the 1940s, sharing the road with buses and vintage automobiles. 1951 · 4 and Washington, Chicago, IL A vintage tan and cream interurban railcar with the number 268 and a 'LOCAL KENWOOD' sign, stopped on elevated tracks near a signal tower. A Chicago North Shore and Milwaukee interurban car, number 268, in its original tan and cream livery, stopped at an elevated station. 1951 · 40th and Indiana, Chicago, IL Two red streetcars and vintage cars on a cobblestone street in Chicago, Illinois, in June 1951, with overhead wires and buildings in the background. A street scene in Chicago, Illinois, circa June 1951, featuring two red streetcars and several automobiles on a cobblestone street with streetcar tracks and overhead wires. June 1951 · Ogden and Roosevelt, Chicago, IL A green and cream streetcar with a red stripe, signed 63-CENTRAL PARK, rounds a curve on a brick street with streetcar tracks; a brick hotel building is at left, trees and parked 1940s cars are behind it, and a dark storm sky is overhead. Chicago Transit Authority streetcar 4023 on route 63 to Central Park on the brick pavement at 64th Street and Stony Island Avenue, likely about 1949 to 1953. July 1, 1951 · 64th and Stony Island, Chicago, IL A white, orange, and blue streetcar with the number 1023 on its front is stopped at an intersection on a cobblestone street, with vintage cars and a brick building in the background. A Chicago Transit Authority PCC streetcar, number 1023, heads toward 63-Central Park on a cobblestone street lined with 1950s cars and a brick hotel. July 1, 1951 · 64th and Stony Island, Chicago, IL An overhead view of a red and cream Peter Witt streetcar on a wide city street with vintage automobiles and crowds of pedestrians on the sidewalks. A Chicago Surface Lines Peter Witt streetcar, number 3, travels down a busy downtown street, likely State Street, in the late 1940s. July 17, 1951 · State and Van Buren, Chicago, IL A black-and-white photo showing two trolleybuses on a city street with multiple vintage automobiles and a Sears store in the background. Two Chicago Transit Authority trolleybuses, including number 788, operate on a city street lined with 1950s-era buildings and automobiles. 1952 · Lawrence and Ravenswood, Chicago, IL Black-and-white photo of a streamlined two-tone streetcar numbered 4008 with its trolley pole raised, moving past a tall brick building and a Y.M.C.A. billboard. Chicago Transit Authority PCC streetcar 4008 at Wabash and 8th in Chicago, with a Y.M.C.A. hotel billboard behind it. 1952 · Wabash and 8th, Chicago, IL Black-and-white photo of a two-tone streamlined streetcar with its trolley pole raised, signed 36 STATE-KINZIE, on a street under tall trees. Chicago Transit Authority PCC streetcar [?]197 on route 36, signed STATE-KINZIE, on a tree-lined street, likely in the 1950s. 1952 · 36 and Wisconsin A red and cream streetcar numbered 3164 is parked in a rail yard, with overhead wires visible and other scrapped cars in the background. Chicago Surface Lines Master Unit streetcar no. 3164, painted in red and cream livery, sits in a rail yard under overcast skies. 1952 · 77th and Vincennes, Chicago, IL A vintage black-and-white photograph of Chicago Surface Lines streetcar 3359 on a city street, with its destination sign reading 'Cottage Grove Ave' and an ad for Lincoln Park Zoo on the front. The car is on a street lined with buildings and has a Coca-Cola sign on a building above it. Chicago Surface Lines Master Unit streetcar 3359, operating on the Cottage Grove Avenue line, photographed in the 1930s or 1940s. 1952 · 4 and Wabash A green and cream streetcar with a single trolley pole runs on a wide, curving bridge approach beneath a massive dark steel truss frame. A traffic signal stands on a concrete median, and a dark old sedan drives away at the right. A Chicago Transit Authority PCC streetcar, likely number 72[?]6, crosses a bridge under a large steel truss structure. The note places it at Western Avenue and 31st Boulevard in Chicago. 1952 · Western and 31st Blvd, Chicago, IL A black and white photo from the 1950s shows a CTA bus on a city street with Wrigley Field in the background, surrounded by classic cars and pedestrians. A Chicago Transit Authority New Look bus, number 1005, on route 152 ADDISON, drives down Sheffield Avenue past Wrigley Field in the late 1950s. 1952 · 152 and Sheffield A red and cream streetcar with the number 672 on its front navigates a sunny city street, with pedestrians on the sidewalk and storefronts in the background. A Chicago Surface Lines streetcar, number 672, travels down a city street lined with early 20th-century buildings and storefronts. 1952 · State and Randolph, Chicago, IL A red and cream streetcar travels down a busy urban street lined with vintage cars and tall buildings under a clear sky. A Chicago Surface Lines Peter Witt streetcar, number 2143, on route 25, travels down a bustling city street in the late 1940s. 1952 · 45 and Jackson, Chicago, IL A red and green Chicago North Shore and Milwaukee interurban train, led by car 759, on elevated tracks with city buildings in the background under a partly cloudy sky. A Chicago North Shore and Milwaukee interurban train, led by car 759, rounds a curve on an elevated structure in Chicago. 1952 · Sheridan and Irving Pk., Chicago, IL A dark blue Pacific Electric Railway electric locomotive numbered 1622 is coupled to a brown caboose on a street with overhead wires. Pacific Electric Railway electric locomotive 1622, a C-1 class unit, is seen coupled to a caboose on a street-running track. June 1952 · Torrance, CA A red and cream vintage streetcar numbered 3164, identified as a Chicago Surface Lines Master Unit, is parked in a rail yard with overhead wires visible and a route number 4 sign on the front. Chicago Surface Lines Master Unit streetcar 3164, painted in red and cream livery, is pictured in a yard under an overcast sky, with its route number 4 displayed on the front. June 1952 · 77th and Vincennes, Chicago, IL A red and cream interurban car numbered 396 travels on an elevated wooden trestle, surrounded by greenery with a network of tracks in the background. A Chicago North Shore and Milwaukee interurban car, number 396, navigates a wooden trestle in a lush, green setting. June 1952 · Loop, Chicago, IL A cream and green streetcar with a trolley pole and a C route sign turns across a downtown intersection with tracks, while pedestrians cross in front of tall office buildings. A San Francisco Municipal Railway streetcar showing route C turns through the intersection of 1st and Market streets in San Francisco. July 1952 · Cline and 1st and Market, San Francisco, CA A row of red Birney streetcars is parked inside a large brick carbarn with the number 5, 6, and 7 painted above the bays; a 'CITIES SERVICE' sign is visible on the building's corner. Chicago Surface Lines Birney streetcars at the South Chicago carbarn in the 1930s. July 1, 1952 · 69th and Lashland, Chicago, IL A black and white photograph of a vintage interurban car, numbered 4, with a destination sign reading 'HOWARD B', on a set of tracks with overhead wires and a wooden utility pole in the background. Chicago North Shore and Milwaukee interurban car #4, a Master Unit, photographed on its private right-of-way in Skokie, Illinois. July 29, 1952 · Skokie, IL A green and cream streetcar with a rounded front and a trolley pole turns on a curved brick-paved track between dark brick buildings on a sunny day. Chicago Transit Authority PCC streetcar 707[?], signed 22 81-HALSTED, rounds the loop track at Clark and Howard in Chicago. 1953 · Clark and Howard, Chicago, IL A vintage Chicago streetcar numbered 1783, running on the Lake route, is shown in a city street with a Ford dealership sign in the background and passengers visible inside. Chicago Surface Lines Master Unit streetcar 1783 on the Lake route at the intersection of Lake and Dearborn Streets in Chicago, circa 1950s. 1953 · Lake and Dearborn, Chicago, IL A green and cream Chicago Surface Lines streetcar numbered 1733 is stopped on a city street under an elevated structure, with pedestrians nearby and storefronts in the background. Chicago Surface Lines Master Unit streetcar 1733 on Lake Street under the elevated tracks on a sunny day. 1953 · Lake and Dearborn, Chicago, IL A red electric interurban train car numbered 34 is on a set of tracks next to a grassy area, with a water tower and vintage cars in the background. A red Chicago Aurora and Elgin interurban car, number 34, heads toward Wheaton on a private right-of-way in Maywood, Illinois. 1953 · 1st Ave, Maywood, IL Two vintage Chicago Aurora and Elgin interurban railcars, 3003 and 3004, travel on a track bordered by grass and trees, with a large water tank visible behind them under an overcast sky. A pair of Chicago Aurora and Elgin interurban cars, numbered 3003 and 3004, on a private right-of-way with a water tower in the background. 1953 · Elgin Gas Work Spur A black and white photograph of a classic PCC streetcar in Chicago, numbered 1208 and heading for Morgan Street, passing under a large bridge sign for Englewood Union Station. A Chicago Transit Authority PCC streetcar, number 1208, on route 36 to Morgan Street, is pictured under the Englewood Union Station bridge. 1953 · 36 and State A green and cream streetcar on a cobbled street with tracks under overhead wires. A pale blue station wagon and a man crossing the street are in the foreground, and parked cars and old brick buildings with shop signs line the street. A Chicago Transit Authority PCC streetcar signed for Route 22 in summer street traffic in Chicago, Illinois. 1953 · Clark and Chicago, Chicago, IL Black-and-white photo of a streamlined streetcar with a single trolley pole, signed 36 119-MORGAN, coming out from beneath a riveted steel railroad bridge lettered ENGLEWOOD UNION STATION. A Chicago Transit Authority PCC streetcar on route 36, signed for 119-Morgan, comes out from under the Englewood Union Station railroad bridge on State Street near 64th Street, Chicago. 1953 · State and 64th St., Chicago, IL A red and cream streetcar, number 1759, turns on a city street with an elevated train structure overhead, surrounded by 1950s-era cars and a large movie billboard on a building. A Chicago Surface Lines Master Unit streetcar, number 1759, navigates a turn on a city street under an elevated structure, with a 1950s Billboard for 'Red Stiff' visible in the background. June 14, 1953 · Randolph and Franklin, Chicago, IL Elevated view down a busy downtown Chicago street with a green and cream streetcar on double track, crowded sidewalks, a mail truck in the foreground and a neon Harding's sign at lower right. A Chicago Transit Authority PCC streetcar approaches on a brick-paved downtown street lined with shoppers and Harding's restaurant sign, seen from an elevated vantage point. June 15, 1953 · Washington and Franklin, Chicago, IL A green and cream PCC streetcar on a cobblestone street in Chicago, surrounded by pedestrians, vintage cars, and storefront signs including 'Harding's' and 'U.S. Mail'. A Chicago Surface Lines PCC streetcar travels downtown on a sunny day in the late 1930s or 1940s, passing storefronts and pedestrians. June 15, 1953 · Washington and Franklin, Chicago, IL A vintage elevated train with a cream and maroon livery travels on wooden-decked tracks between tall buildings, passing a signal marked '0' and a building with a 'Rubin Grand' sign. A Chicago Rapid Transit Company 4000-series car, number 2[?]94, navigates the complex trackwork of the Wells Street Terminal, with a second car in the background. July 1953 · Wells St. Term. A red streetcar runs down the center of a bustling city street, surrounded by vintage cars and pedestrians under an elevated structure. A red Chicago Surface Lines Peter Witt streetcar navigates a busy city street lined with mid-century storefronts and parked cars. August 2, 1953 · 52 and Garfield Front view of a dark-bodied CTA bus with the number 5306 and a 'Van Buren - Racine' destination sign, driving on a snowy city street next to elevated train tracks. A Chicago Transit Authority New Look bus, number 5306, on the Van Buren-Racine route in winter. August 9, 1953 · Van Buren and Racine, Chicago, IL Three vintage red and white streetcars parked in front of a brick carhouse on a sunny day. Three Chicago Surface Lines Master Unit streetcars, numbers 6151, 3196, and 554, parked in front of the Ashland Carhouse. August 23, 1953 · Ashland Carhouse A green and cream PCC streetcar numbered 4263 travels down a busy Chicago street with vintage cars and pedestrians, under clear skies. Chicago Surface Lines PCC streetcar #4263 on State Street, likely in the early 1950s, surrounded by vintage automobiles and city storefronts. August 23, 1953 · State and Van Buren, Chicago, IL A green and cream streetcar on tracks in the middle of a busy downtown street lined with tall buildings, parked cars, a yellow taxi and pennant banners on the lamp posts. A Chicago Transit Authority PCC streetcar heads south on State Street at Van Buren under "College Days" banners, about 1953–57. August 23, 1953 · State and Van Buren, Chicago, IL A vintage red-roofed Chicago Motor Coach Company bus, number 64, is parked on a paved lot, with a man walking nearby and trees and buildings in the background. A Chicago Motor Coach Company bus, number 64, operating on the Lake Front-State Street Shuttle Service in a parking lot area. August 27, 1953 · Columbus Dr. and Monroe, Chicago, IL A yellow Union Pacific diesel locomotive numbered 1720 stands in a rail yard on a clear, sunny day with stacks of steel rails in the foreground. A Union Pacific GP9 diesel locomotive, number 1720, is shown in a yard, displaying its classic yellow livery with red pinstripes and grey roof. c. 1954 to 1970 A yellow Union Pacific locomotive number 1720 sits on tracks in a rail yard with another locomotive partially visible in the background. A Union Pacific GP9 diesel locomotive, number 1720, is parked in a rail yard. c. 1954 to 1970 A black and white photo of a Chicago Transit Authority trolleybus, number 9523, parked on a street with overhead wires and buildings in the background. A Chicago Transit Authority trolleybus, number 9523, is shown on a city street, likely in the late 1960s or early 1970s. c. 1954 to 1973 Two bright orange CA&E electric locomotives lead a freight train on multiple tracks under overhead wires on a sunny day. Two CA&E electric boxcab locomotives, 2001 and 2002, lead a freight train through Hillside, Illinois, under the overhead wires of their private right-of-way. 1954 · Hillside, Hillside, IL Two green and cream streetcars with trolley poles stand side by side on a street under overhead wires, with 1950s cars and trucks at the left and brick buildings behind. PCC streetcars 4396 and 7223 meet on route 22, with 4396 signed for 81-Halsted, likely at Wentworth and Garfield Boulevard in Chicago. 1954 · Wentworth and Garfield Blvd, Chicago, IL A black and white photo of a Chicago Transit Authority bus from the 1950s on a crowded city street, surrounded by pedestrians, vintage cars, and theater marquees. Chicago Transit Authority bus #1829 on route 49 State St, navigating a busy downtown street in the mid-1950s, with the State Lake Theater and vintage automobiles in the background. 1954 · 149 and Lake, Chicago, IL An interurban train with a green and orange car, numbered 713 and marked 'MUNDELEIN', is stopped at a station platform under overhead wires, with a 1950s car parked nearby. Chicago North Shore and Milwaukee interurban car 713, a Master Unit, is pictured at the Mundelein station in summer. 1954 · Mundelein, IL