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According to Wikipedia:

TWA flew to Europe nonstop from O'Hare starting in 1958

The Great Circle Route distance from ORD/KORD to LHR/EGLL is 3953 miles. Other major European airports would have been farther away.

What aircraft were capable of making that non-stop flight in 1958 (also, how long would it have taken)?

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    $\begingroup$ Many earlier transatlantic flights stopped in Shannon (SNN / EINN) before or after the Atlantic crossing, they didn't necessarily fly directly to their final destination: "non-stop to Europe" isn't the same as non-stop to Paris, for example. It's still over 3000 miles, but it did cut down the distance (and also importantly, the time) needed for a crossing. $\endgroup$ – Pondlife Jul 24 '15 at 13:46
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The first scheduled trans-atlantic air service was made possible with Zeppelins. The LZ-127 started flying the route in 1931, mostly to Lakehurst, NJ, or Pernambuco in Brazil, but was disassembled in 1940.

The first airliner which was able to cover the distance (back then it was Berlin - New York) was the Focke-Wulf 200, which in 1938 needed almost 25 hours East-West and 20 hours on the return leg. With its slow cruise speed, wind made a lot of difference. Sadly, the US did not allow Lufthansa to start the scheduled service it had planned to open in 1939. Lufthansa had opened regular air mail services in 1934 between Europe and South America using flying boats and a relay ship in the middle of the Atlantic. Air France added its transatlantic mail service flying from Africa to South America and back.

The first heavier-than-air transatlantic passenger service opened between New York and Marseille in 1939 on Boeing 314 Clippers operated by Pan Am. It crossed the Atlantic between Foynes, Ireland and Botwood, Newfoundland. A British service, also using flying boats, was in preparation but stopped by the beginning of WW II.

In the 1950s, there were already several options for transatlantic air travel, but none of them non-stop from Chicago: Pan Am, TWA, Trans Canada Airlines (TCA), BOAC (successor of Imperial Airways), and Air France all operated large propeller aircraft which covered the distance with refueling steps, typically in Gander (Newfoundland) and Shannon (Ireland). Typical aircraft were the Douglas DC-4 and DC-6, and the Lockheed 149 Constellation, but also the French Latecoere 631 flying boat was used until 1955. Of these airlines, only Pan Am and BOAC serviced O'Hare in 1957, before the first international terminal opened there in the following year.

Still, the prevailing eastward wind made the East-West crossing hard and required airlines to reduce payload, and only the advent of faster airliners like the Douglas DC-7 (from 1956) and the Lockheed 1649 Starliner (from 1957) made the transatlantic services more reliable and economical. Beginning with the DC-7C, their range was sufficient to support transatlantic service directly from Chicago O'Hare.

In October 1958 the first transatlantic jet airliner service was opened by BOAC using the de Havilland Comet 4, followed shortly after by Pan Am, operating the Boeing 707 and connecting London with New York (with an occasional refueling stop at Gander on westbound flights). O'Hare could only participate in this progress after its main runway was extended to accommodate large jets in June 1960.

Therefore, the most likely airplanes to fly transatlantic directly from O'Hare would have been the DC-7C (but operated by Pan Am, not TWA), the Lockheed L-1049G and the L-1649, which both were operated by TWA. For the flying time, the 3628 miles from JFK/Idlewild to Paris Orly took 14¼ hours with the DC-7C and 14.83 hours with the Lockheed 1649. So it is fair to assume a flying time of 15½ to 16 hours for the slightly longer distance between Heathrow and O'Hare.

Quote from Wikipedia:

In January 1958 Pan American scheduled the DC-7C from Orly to Idlewild in 14 hr 15 min; TWA scheduled the 1649 in 14 hr 50 min.

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    $\begingroup$ The Wiki quote specifies non-stop - Shannon, Ireland is in Europe, so I would consider a non-stop flight from Chicago to Shannon as qualifying for that. Is Greenland considered Europe? Says he, showing his high-quality American education... $\endgroup$ – FreeMan Jul 24 '15 at 16:16
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    $\begingroup$ @FreeMan No, Greenland is part of North America, not Europe. It's only 200 miles from Canada at its closest point vs. over 900 miles from (mainland) Norway. However, since it's owned by Denmark, it could be considered politically European, even though it's geographically considered to be part of North America. $\endgroup$ – reirab Jul 24 '15 at 19:24
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    $\begingroup$ @DrZ214 Iceland is politically in Europe, but geologically is the border between the North American plate and the European plate, which is why it's so tectonically active. As it happens, Reykjavik is in the western half of Iceland, so it's geologically North American, not European. $\endgroup$ – Mike Scott Jul 25 '15 at 17:57
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    $\begingroup$ Ah, the Lockheed Constellation - The World's Best Tri-Motor! ;) $\endgroup$ – egid Jul 26 '15 at 3:30
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    $\begingroup$ During WWII RCAF Ferry Command flew over 9,000 brand new aircraft non-stop from North America to Europe. The crews were returned to NA in what could be termed a passenger service... $\endgroup$ – DJohnM Oct 15 '15 at 19:31
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In 1958, Trans World Airlines operated primarily Lockheed Constellation. Its range is listed as 4,700 nmi, which makes it suitable for that route.

The Wikipedia page about TWA lists when they introduced and retired each type. According to that table the only long range aircraft they had in 1958 was Constellation; B707 only being introduced in 1960.

Similar aircraft that were in service by 1958 with other airlines and had over 4,000 nmi range that is needed for the route were Douglas DC-6A and B, Douglas DC-7, Boeing 377 and already turboprop Bristol Britannia. But TWA did not have any of those types, so they were not used on that particular route.

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    $\begingroup$ The Douglas DC-4 was built with transatlantic flights in mind, and would not have been completely phased out (in favor of the DC-6 and -7) in 1958. Swissair ran the DC-4s on the Geneva to New York route (with stopovers: sr692.com/fleet/14_dc4/index.html) though with the 4200 mile range non-stop flight should have been possible with little weight on board. Perhaps on the return trip to Europe with tail winds? $\endgroup$ – ALAN WARD Jul 24 '15 at 13:44
  • $\begingroup$ It looks like the DC-7 Seven Seas variant was the first one to fly regularly transatlantic non-stop. $\endgroup$ – ALAN WARD Jul 24 '15 at 13:50
  • $\begingroup$ Also for reference... en.wikipedia.org/wiki/Category:Airliners_1940%E2%80%931949 $\endgroup$ – J... Jul 24 '15 at 15:23
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There were regular transatlantic flights even before the 1950s. For example, in 1948, my father was among the passengers in a DC-4 flying the regular route from Madrid to Lima with FAMA, an Argentinian airline. The crossing of the South Atlantic was made from Dakar in Senegal to Natal, in Brazil.

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