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

Photos

A red and cream vintage streetcar, number 585, is turning on streetcar tracks in front of a house, with overhead wires above. A red and cream Milwaukee Master Unit streetcar, number 585, navigates a turning loop on a sunny autumn day. 1950 A vintage red streetcar with the number 6152 travels down a cobblestone street lined with brick buildings, including a Studebaker dealership and a Drewrys Beer billboard. A red and cream Chicago Surface Lines Master Unit streetcar, number 6152, runs on a cobblestone street past a Studebaker dealership and a Drewrys beer billboard. 1950 · Lawrence and Clark, Chicago, IL A vintage black-and-white photo of a Chicago Transit Authority bus with fleet number 2503, showing its front and side on a paved street with embedded track. A Chicago Transit Authority Flxible New Look bus, number 2503, on a city street in the 1960s. 1950 · Monroe and Dearborn, Chicago, IL 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 red and cream vintage streetcar with the number 7 on its front, running on city streets with old buildings and a 1940s car in the background. A Chicago Surface Lines Master Unit streetcar, number 7, on the 66 Michigan route in downtown Chicago. 1950 · 66 Michigan, Chicago, IL A red and cream streetcar with the number 3111 turns on a street corner, with a brick building and trees in the background. A Chicago Surface Lines Master Unit streetcar, number 3111, turns a corner on a sunny autumn day, with passengers visible inside. 1950 · Cottage Grove and 111th, 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 A red and cream trolleybus on a sunny day, with overhead wires, passengers inside, and vintage cars and buildings in the background. A Chicago Surface Lines Brill T-44 trolleybus, number 834, on the 85 Central-Lexington route, captured in a summer street scene. 1950 · 85 and Central A red and cream streetcar marked 'LAKE' and number 1758 is stopped on a city street with a red work vehicle beside it and two men on its roof, with tall buildings in the background. A Chicago Surface Lines Birney streetcar, number 1758, on the Lake route, is attended by a work vehicle and two workers on its roof on a city street in the late 1940s. 1950 · Franklin and Randolph, Chicago, IL Black-and-white photo of a streetcar numbered 1674 on a city street beneath an elevated train line with a car numbered 2535, located at the corner of Van Buren and Clinton streets in Chicago. A Chicago Surface Lines Birney streetcar, number 1674, operates under an elevated structure with a Chicago Rapid Transit Company 4000-series car, number 2535, above at Van Buren and Clinton streets. 1950 · Van Buren and Clinton, Chicago, IL A vintage wooden rapid transit car on an elevated track in a city, with tall buildings in the background. A Chicago Rapid Transit Company 4000-series rapid transit car, number 321, on an elevated structure. 1950 · Clark and Lake, Chicago, IL Side view of a vintage white and green Chicago Motor Coach Company bus, number 582, with advertisements, driving on a tree-lined street. A Chicago Motor Coach Company New Look bus, number 582, operates on the Boulevard Route in a suburban setting on an overcast summer day. 1950 · Columbus and Park, Chicago, IL A vintage motor bus with number 582 and Chicago Motor Coach Company lettering is driving down a tree-lined street. A Chicago Motor Coach Company New Look bus, number 582, in service on The Boulevard Route. 1950 · Columbus Park A side view of a Chicago Motor Coach Company bus, numbered 1008, parked inside a large bus garage with its engine compartment open. A Chicago Motor Coach Company New Look bus, number 1008, inside a bus garage. 1950 · Diversey and Keeler, Chicago, IL A side view of a vintage Chicago Motor Coach Company bus, number 1008, with a streamlined body, parked inside a large, well-lit bus garage. A Chicago Motor Coach Company GMC TDH-3610 bus, number 1008, is shown in a bus garage, likely in the late 1930s or early 1940s. 1950 · Diversey and Keeler, Chicago, IL A red and cream Chicago Surface Lines streetcar numbered 1001 is shown from a three-quarter front view on a city street, with a large billboard for 'LEAF' cigarettes on a building behind it. A Chicago Surface Lines Master Unit streetcar, number 1001, travels along a cobblestone street under a 'LEAF' cigarette billboard. May 14, 1950 · Wells and Hubbard, Chicago, IL A vintage wooden interurban train car numbered 1237 is parked on tracks in a rail yard, with a dark green and wood-trim livery, under clear skies. Interurban car 1237 of the Chicago North Shore and Milwaukee sits in a yard on a sunny day. June 1950 · Lower Wilson A red and cream interurban car numbered 699 with a destination sign reading 16 AUSTIN, traveling on an elevated wooden trestle with overhead wires. Chicago North Shore and Milwaukee Master Unit 699 on an elevated structure in Chicago. June 1950 · Roosevelt over Illinois Central Tracks, Chicago, IL A vintage red streetcar with the number 556 turns a corner on a city street, with brick buildings and a classic automobile in the background. A red Chicago Surface Lines Master Unit streetcar, number 556, rounds a corner on a sunny day in the late 1940s. June 1950 · Paulina and Madison, Chicago, IL A vintage red Chicago streetcar with the number 551 travels down a busy urban street lined with parked cars and a white delivery truck. A red and cream Chicago Surface Lines Master Unit streetcar, number 551, operates on a cobblestone street in Chicago. June 1950 · State and Roosevelt, Chicago, IL Elevated view of a green and cream streetcar on a cobblestone street with double tracks. People stand at its front beside a parked car, dark sedans pass in the next lane, and billboards and old buildings line the far side. A Chicago Transit Authority PCC streetcar signed for Broadway-Devon on State Street at Roosevelt Road, Chicago, in the 1950s. June 1950 · State and Roosevelt, Chicago, IL A street scene with a cream and green CTA bus and a red CTA streetcar under an elevated train structure, with pedestrians on the sidewalk and vintage cars parked alongside a brick-paved street. A Chicago Transit Authority GMC bus and a PCC streetcar share a sun-drenched street beneath an elevated structure on Washington & Wells in the late 1940s. June 8, 1950 · Washington and Wells, Chicago, IL A street scene in downtown Chicago featuring a red streetcar, green and yellow buses, and vintage automobiles on a cobblestone street, with an elevated train structure overhead and neon signs on surrounding buildings. A Chicago Surface Lines streetcar and motor buses operate on a downtown street under an elevated railway in the late 1940s. June 8, 1950 · Washington and Wells, Chicago, IL A busy city street at dusk with vintage cars, a red trolleybus, and green-and-cream double-decker buses under an elevated train structure, with neon signs for 'Hardin's' and 'Schroder Paints' in the background. A bustling Chicago street scene from the mid-1950s featuring Chicago Transit Authority double-decker buses, a trolleybus, and 1950s automobiles under an elevated structure with neon signs. June 8, 1950 · Washington and J Wells High-angle view of a bustling city street with multiple streetcars, cars, and pedestrians under a clear sky. Several streetcars operate on a busy city street lined with tall buildings and vintage automobiles. June 27, 1950 A high-angle, sunlit street scene in Chicago with multiple yellow and cream streetcars running on tracks between rows of cars and pedestrians on the sidewalks. High-angle view of several vintage streetcars and 1940s automobiles navigating a busy downtown Chicago street. June 27, 1950 A side and front view of a vintage orange and maroon interurban streetcar with the number 1721 and a destination sign reading 'LAKE B' on a city street with overhead wires. Chicago North Shore and Milwaukee Master Unit 1721, in orange and maroon livery, is shown on the Lake Bluff line in Chicago. July 1, 1950 · Lake B and Harlem, Chicago, IL An elevated view of a street in Chicago with two trolleybuses on tracks, surrounded by classic cars and onlookers on the sidewalks. Two Chicago Surface Lines trolleybuses, one in orange and cream and one in cream and green, navigate a busy cobblestone street lined with pedestrians and 1950s automobiles. July 3, 1950 · Calumet A vintage red and cream streetcar numbered 723, with a destination sign reading 'THE ISLAND', is shown on a cobblestone street with passengers visible through its windows, under overhead wires and next to a building with a 'FLOOR COVERINGS' sign. Chicago Surface Lines Master Unit 723, painted in red and cream, is seen on a street running route, likely near the Clinton and Harrison intersection, with passengers aboard and an advertisement for golf on its front. July 11, 1950 · Clinton and Harrison, Chicago, IL A vintage interurban streetcar with the number 25, in dark green and wood trim, runs on an elevated track through a city neighborhood with a 'Fox Deluxe Beer' billboard in the background. Chicago North Shore and Milwaukee Master Unit car #25 on the Lake Street Loop, circa 1920s. August 1950 · Lake and Paulina, Chicago, IL Front three-quarter view of a green and cream Chicago Transit Authority 2000-series rapid transit car with an 'A LOGAN SQUARE' destination sign, running on an elevated structure under an overcast sky. A Chicago Transit Authority 2000-series rapid transit car on the 'A' line to Logan Square, photographed on an elevated structure in the 1960s or 1970s. September 16, 1950 · Logan Square, Chicago, IL A dark brown Soo Line caboose with the number 141 is parked in a snow-covered rail yard, with green and red boxcars visible in the background. A Soo Line caboose numbered 141 sits in a snowy rail yard alongside other freight cars. October 1950 · Cedar and Whaley, Franklin Park, IL A three-quarter front view of a train of old, wood-bodied elevated cars on an elevated track in Chicago, with large brick and stone industrial buildings in the background under a clear sky. A train of vintage wood-bodied elevated cars on an embankment in Chicago, framed by industrial buildings on a sunny day. October 18, 1950 · Halsted St., Chicago, IL A red and cream streetcar with the number 567 and 'NORTH WESTERN STATION' shown on its front is stopped on a city street with cars and brick buildings in the background. A Chicago Surface Lines Master Unit streetcar, number 567, operates on a street in front of storefronts including Schlesinger's Meats. October 18, 1950 · Armitage A green and cream streetcar numbered 4206, with a HALSTED-79 sign, travels on track laid over fresh ballast through a rubble-strewn lot, with overhead wires, wooden poles and brick industrial buildings behind it. Chicago Transit Authority PCC streetcar 4206, signed for Halsted-79, runs on temporary track through a cleared construction site at Halsted and Congress in Chicago. October 29, 1950 · Halsted and Congress, Chicago, IL A vintage orange and cream streetcar with the number 1746 and route 58 sign, moving down a city street lined with 1930s-era storefronts and billboards under a clear blue sky. A CSL Master Unit streetcar, number 1746, on route 58, traveling on a cobblestone street in Chicago. October 29, 1950 · Ogden and Van Buren, Chicago, IL A red and cream Chicago Surface Lines streetcar, number 436, is stopped on a city street with several passengers standing on its running board, surrounded by vintage 1940s automobiles and a Lay's potato chips billboard. A Chicago Surface Lines Master Unit streetcar, number 436, is packed with passengers on a fan trip in downtown Chicago, circa 1948-1950. October 29, 1950 · Roosevelt and Wabash, Chicago, IL A vintage orange streetcar on city streets at dusk, with a classic car and pedestrians nearby. A Chicago Surface Lines Master Unit streetcar, number 1786, is seen at the Ogden and Ashland intersection under dusk lighting. October 29, 1950 · Ogden and Ashland Blvd., Chicago, IL An old electric train car with 'RAPID TRANSIT' lettering on its side travels on elevated tracks near a building with a 'MOODY PIE CO' sign. A Chicago North Shore and Milwaukee Master Unit interurban car on an elevated track, with the Moody Pie Company building visible in the background. October 30, 1950 · Lake Paulina An elevated train of vintage wooden 'L' cars travels across a metal truss bridge above a river, with a large building visible behind it under a clear sky. A train of Chicago Rapid Transit Company 4000-series 'L' cars crosses an elevated truss bridge over a river, with a large building in the background. November 1, 1950 · Canal St. Union Sta., Chicago, IL An early 20th-century interurban car with a cream and maroon livery and an open front platform is parked on an elevated wooden structure. Snow is visible on the platform and the car's roof. A Chicago North Shore and Milwaukee Master Unit interurban car, likely in the 1950s, rests on an elevated wooden structure in a snowy, overcast setting. November 6, 1950 · Irving Pk, Chicago, IL Two green and cream streetcars, one approaching and one going away, on a brick street under trolley wires, with brick warehouses at left and a GMC Trucks sign at right. Two streetcars, the leader signed for Pulaski, run on a brick-paved street near 5th Ave and Harrison, likely on the Chicago Transit Authority. 1951 · 5th Ave and Harrison, 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 Side view of a dark green and cream streamlined streetcar with a red stripe, numbered 4020, on curving track in front of a brick building with a large painted sign reading Supply & Hardware Corp., beneath a dense web of overhead wires. Chicago Transit Authority streetcar 4020 on the turning loop at 63rd Place and Central, Chicago. 1951 · 63rd Pl and Central, Chicago, IL 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 streetcar with the number 726 and destination Halsted is stopped on a city street, with tall buildings and a 1950s car in the background. Chicago Surface Lines Master Unit streetcar 726 on the Halsted route in downtown Chicago, circa 1950-1953. 1951 · 42 and Washington 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