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Imagine the scenario where an airline flys a short 30 minute route which crosses a timezone going west. They could theoretically leave at 00:15 (local) and arrive at 23:45 local the previous day. I'm wondering if there are any airlines which fly such a route.

P.S. I'm specifically interested in how the airline allows booking such a flight and the UI that is presented, but am leaving this question more general for any flights that do this.

P.P.S. If someone could help with the tags for this question, it'd be much appreciated.

I found such a route for you. KATL (Atlanta) to KHSV (Huntsville, AL) is a 57 minute hop from the Eastern time zone to the Central time zone. It appears how you would expect:

Back when Concorde was still a thing, British Airways' motto was 'Arrive before you leave', illustrating how you could arrive in North America sooner (in local time) than when you left Europe.

UA892 leaves ICN at 6PM Friday (KT) and arrives at SFO at 11:30AM Friday (ET).

There's dozens of flights that leave Korea/Japan/etc and go to the US West Coast that arrive "before" they take off.

I'm not able to find a flight in these circumstances that leaves in the early AM from the west side of the Pacific, because that would seem to meet your criteria of arriving the previous day. The same flight leaving at 6AM Friday would arrive 11:30PM Thursday.

Yes, there are loads of these. My personal most frequent return flight - Atlanta to Nashville - is a good example. It's 35-40 minutes flying time, but moves from the Eastern time zone to Central, thus landing 20-25 minutes before it took off.

Much more extreme examples happen when you cross the International Date Line going East. For example, I've flown from Seoul (Incheon,) South Korea to San Francisco in about 10.5 hours. However, Seoul's time zone is 17 hours ahead of San Francisco's, so, despite the flight being 10.5 hours in duration, it landed 6.5 hours before it took off in local time.

Even flights with 14+ hour duration from East Asia to the U.S. mainland frequently land earlier than they take off.

The most extreme examples would be from an airport just on the Western side of the International Date Line to one just on the East side. These can land almost a full day before their departure in local time. In some cases, it's even possible to land slightly more than a full day before their departure, such as flights from the Line Islands of Kiribati (UTC+14) to, say, American Samoa (UTC-11).

And this is why aviation always uses Zulu time (UTC), not local time.

Yes, being a pretty frequent traveler between the US and Australia I've very often technically 'arrived' before I left. I tend to book through Orbitz and while the trip to Australia is often marked with a +2 to show that crossing the date line adds another day to your trip (ie, you leave on Monday and get there on Wednesday even though the flight is only 13 hours), when you return it's common to find flights that look like this one below. Where you leave Australia at 9:35am, fly for over 13 hours, and arrive three hours earlier:

Personally, I'm not a big fan of how Orbitz doesn't show the actual dates with the times. It'd help clear up confusion here.

I like JQ129 from Auckland (AKL) to Rarotonga (RAR). You arrive 19 hours before you depart.