Flag Stop 4,614 transit photos from Chicago and beyond, mostly 1940s–2000s
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1449 photographs
A vintage black-and-white photo of a double-decker bus with 'Chicago Motor Bus Company' lettering on its side and number 1155 on its front, showing passengers on the upper deck and a clear destination sign. A Chicago Motor Coach Company double-decker bus, number 1155, is shown on a summer day, likely in the 1910s or 1920s, with passengers on its open top deck and destination sign reading 'DOWN TOWN 7th Lake Shore Drive'. May 9, 1919 · Lake Shore Drive, Chicago, IL A vintage black and white photo of a double-decker bus labeled 'Chicago Motor Bus Company' with a 'Soldiers Welcome Sailors' sign on its roof, driving down a city street with passengers visible on the top deck. A Chicago Motor Bus Company double-decker bus from the World War I era, carrying passengers and displaying patriotic 'V for Victory' signs. May 9, 1919 · Lake Shore Drive, Chicago, IL A black and white photo shows a vintage streetcar numbered 1211 on a snowy city street with people, old cars, and storefronts, including a 'MEATS' shop and a 'HARD LAUNDRY'. A Chicago Surface Lines Master Unit streetcar, number 1211, is stopped on a snowy street under an elevated structure, with pedestrians and early 1930s automobiles nearby. November 16, 1930 · Montrose and Broadway, Chicago, IL 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 streetcar numbered 236 travels on a city street alongside a horse-drawn wagon and early automobiles, under overhead wires. A Chicago Surface Lines Peter Witt streetcar, number 236, at the corner of Clinton and Roosevelt streets, sharing the street with horse-drawn and motorized traffic. 1932 · Clinton and Roosevelt, Chicago, IL A black and white street scene from the 1930s showing a Chicago Surface Lines streetcar on a cobblestone street with an elevated railway in the background. A Chicago Surface Lines Master Unit streetcar, number 3259, heads to the North Western Station on a winter day in the 1930s. May 7, 1932 · Franklin and Washington, Chicago, IL A black and white photo of a vintage streetcar on a city street with a pedestrian crossing and several cars from the era. A Chicago Surface Lines Peter Witt streetcar, number 5460, operates on a city street in the early 1930s. March 1933 · Halsted and 80th St, Chicago, IL 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 black and white photo of two PCC streetcars on a Chicago street, with overhead wires and houses in the background. Two Chicago Surface Lines PCC streetcars, numbers 187 and 178, are seen on the 76 DIVERSEY-WESTERN route at the intersection of Diversey and Harlem in Chicago, likely in the 1940s. 1938 · Diversey and Harlem, 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 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 vintage black and white photo of a Chicago streetcar numbered 1735, with several people near it and a car parked alongside, in front of a building labeled UPTOWN. A Chicago Surface Lines Master Unit streetcar, number 1735, is shown on a street in front of a building marked 'UPTOWN'. April 1941 · Broadway and Lawrence, Chicago, IL A black and white photo of a crowded street in Chicago where a Chicago Surface Lines streetcar, number 1748, is stopped at an intersection while pedestrians cross the tracks. Chicago Surface Lines streetcar 1748, a Master Unit car, navigates a busy street crossing at Clark and Addison in Chicago during the late 1930s. October 5, 1941 · Clark and Addison, Chicago, IL A bustling 1940s street scene in Chicago with two vintage streetcars, many pedestrians, and classic automobiles at the intersection of Clark and Addison, with Wrigley Field visible in the background. Chicago Surface Lines Master Unit streetcars 1715 and 1760 at Clark and Addison, with pedestrians crossing in front of Wrigley Field. October 5, 1941 · Clark and Addison, 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 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 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 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 a streamlined streetcar with a dark lower body and white upper body. It has a cream stripe sweeping up over its single headlight, the number 4022 on the front, and a sign reading 20 Dearborn-Monroe. It stands on pavement in front of bare trees and houses, and a second stre Chicago PCC streetcar 4022, signed for route 20 Dearborn-Monroe, likely at the Madison and Austin terminal. 1945 · Madison and Austin, Chicago, IL A black and white photograph of a vintage streetcar on a city street, with an elevated train track above and a building with 'HOTEL' signage in the background. A Chicago Surface Lines Master Unit streetcar, number 5091, navigates a street corner under an elevated railway, with a 'HOTEL' sign and a 1930s automobile in the background. 1945 · Root and Halsted, Chicago, IL A vintage black-and-white photo of a Chicago 'L' car, number 1149, with a rear destination sign reading 'EXPRESS HOWARD ST', on elevated tracks with city buildings in the background. A Chicago Rapid Transit Company 4000-series rapid transit car, number 1149, is shown on an elevated structure with a destination sign indicating service to Howard Street. 1945 · Wabash and Congress, Chicago, IL 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 front view of a red and cream Chicago Surface Lines bus, number 856, with the destination '79-WESTERN' displayed, as passengers board on a crowded street. A Chicago Surface Lines White Motor bus, number 856, on the 79-WESTERN route, surrounded by passengers boarding on a city street. March 1945 · Ford City, Chicago, 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 Black and white photo of a vintage Chicago interurban car, number 1766, labeled 'Evanston Express,' stopped on city street tracks with passengers inside and commercial buildings behind. Chicago Rapid Transit Company Plush interurban car 1766, marked for the Evanston Express, on street tracks with buildings of downtown Chicago in the background. 1946 · Franklin, Chicago, IL A black and white photo of a Chicago Motor Coach Company bus number 2500, a Flxible New Look model, parked on a street with a tall tower and a freight car in the background. Chicago Motor Coach Company bus number 2500, a Flxible New Look model, posed for a roster shot on a street in Chicago. 1946 · Diversey and Keeler, Chicago, IL 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 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 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 Black and white photograph of a Chicago Surface Lines motor bus, number 1268, stopped at an intersection with pedestrians crossing and a statue of a mounted rider in the background. A Chicago Surface Lines motor bus, number 1268, is seen at an intersection in the late 1940s, with pedestrians crossing and a prominent equestrian statue in the background. 1946 · 51st St, 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 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 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 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 of a vintage motor bus on a city street with trolley tracks, surrounded by 1940s cars and two pedestrians on the sidewalk. A Chicago Surface Lines bus, number 3425, travels along a street with embedded trolley tracks, likely on route 31 Cottage Grove, in the late 1940s. 1946 · 31 and Pitney Ct., Chicago, 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 black and white photo of a 4000-series 'L' car, numbered 2900, at a station with its destination sign 'LOOP' visible. A Chicago Rapid Transit Company 4000-series rapid transit car, number 2900, is pictured at a station platform with its destination sign reading 'LOOP.' 1946 · Canal St. Union Sta., Chicago, IL A vintage black-and-white photo shows a double-decker bus on a wide city street lined with multi-story buildings and period automobiles, with pedestrians walking on the sidewalks. A Chicago Motor Coach Company double-decker bus, number 114, is pictured on a city street, serving route 51 Sheridan Road, circa 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 1950s GMC New Look bus with the number 1181 and destination 'UNIVERSITY' on a city street with pedestrians and tall buildings in the background. A Chicago Motor Coach Company bus, number 1181, heading for the University, is captured on a city street in the 1950s. 1946 · Chicago, IL A vintage bus with the destination 'MILWAUKEE 63' and fleet number 2874 is surrounded by pedestrians on a city street, with storefronts and a street sign visible in the background. A Chicago Surface Lines bus, number 2874, on the Milwaukee 63 route, with passengers boarding at a busy street corner. October 1946 · State and Adams, Chicago, IL Front three-quarter view of a white CTA bus with fleet number 4308 on a city street, next to a yellow taxi, with tall buildings in the background. A Chicago Transit Authority New Flyer D40LF bus, number 4308, running an express route on a city street, with a yellow taxi nearby. April 1947 · Wacker and Clark, Chicago, IL 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