The shortest flight I’ve been on was between Plattsburgh, NY and Burlington, VT. They’re only about 25 km by air but you have to travel over a lake, so the driving route is much longer.
I once flew from Newark to Someplace in the midwest, changed planes, then flew from Someplace towards Indianapolis, Indiana, landing in Ohio–Dayton, maybe? Seems like it was a place that was almost as close to Indianapolis when driving as it was when flying. But we’d landed abruptly due to thunderstorms. Once the weather where we were, in Indianapolis, and in between finally cleared, we reboarded our plane for one of those flights described above “OK, now we’ve reached cruising altitude and will be descending” hops. The only bad part that we arrived at the airport too late to get the shuttle back to my university, and so I spent the night at the airport, leaving bright and early the next morning.
I think I may have you beat by a few miles, having flown from Philadelphia to Wilkes-Barre. I don’t remember why I thought this was a good idea.
The Oklahoma City to Dallas flight is pretty short.
I once flew from NYC to Indianapolis, out in the morning and back in the evening.
Youtube video here: http://www.youtube.com/watch?v=9pBXjAQX7W8
More photos of the flight here: http://www.alanmoar.flyer.co.uk/orkney/Shortestflight/shortest.htm
Hm come to think of it I think I’ve done SFO to OAK… when I lived in San Jose I had a flight cancelled and trying to get out the same day meant some really interestng routing, and a mad dash from SJC to SFO to catch a flight that left in an hour. (Pre 9/11.) I know I’ve left from OAK before so I think it must’ve been that flight.
While I can’t beat Rasa, in 1989 I did a flight from MHT (Manchester NH) to BOS (Logan Airport in Boston). It was part of a flight to DCA (now Regan National in DC).
I had the same routing on the way home, but it was easier to get off the plane in Boston and take the train back to school in Lowell. (Mid day Monday, tough to get a friend to pick me up in the middle of the school day.)
Using that routing saved me about $200 off the full round trip. (Big $$$ to a college student making about $8/hr)
The flight no longer exists directly, you’d need to connect somewhere, like LaGuardia in New York. By road, it’s 56 miles, and a fairly straight shot down Rt 93.
My shortest flight (I’ve made that trip several times) is from Mexico City to Guanajuato (well, not actually Guanajuato but to the closest international airport). Guanajuato is 170 miles from Mexico City.
One time I was just about the only passenger on the flight. It’s really a flight from Mexico City to Tijuana but it lands in Guanajuato to board more passengers.
Cincinnati Ohio - Columbus Ohio: Total time in the air, less than 15 minutes
Pilot “The seat belt sign won’t be turned off and the flight attendant will not be getting of her seat”
I’ve done St. Louis to Chicago, which is about an hour, IIRC. It was a group of 13 Girl Scouts and our troop leaders going for a weekend in Chicago. We flew Southwest and I got a backwards-facing seat which was quite fun, going up then right back down.
We once flew from Seattle to Vancouver. The drive would take about 3 1/2 hours, that flight took 6. Lots of time sitting on two runways, because the plane was broken.
My shortest flight was from Vancouver BC to Victoria BC. I couldn’t get a Calgary-Victoria flight, so I had to connect through Vancouver. Fifteen minutes, up and down.
Mine is probably St. Thomas, USVI to St.Croix USVI. They are about 40 miles apart and it wouldn’t be that unusual if I was in one of the seaplanes they have there. Instead, I have flown direct from Boston or La Guardi direct to St. Thomas in a very large plane. After dropping people off in St. Thomas, you take off and go right to St. Croix. You have this big plane that sets up an approach as soon as it takes off. It takes less than 15 minutes to be at the gate.
How did you manage with the eels?
My shortest was Detroit to Cleveland, about 45 minutes. When my college choir went to Italy we had to fly Rome-Detroit-Cleveland to get home the day we had hoped.
I can think of several I’ve done:
Gibraltar - Tangier (when it existed) used to be in the Guinness Book of Records as the world’s shortest inter-continental flight - 15 mins.
Santo Domingo (DR) - San Juan (PR) is one of those take off and land before you know it flights, provided you don’t fly in one of those American Eagle tin cans that travel that route along with the real planes. I’ve also heard that it’s the most expensive flight in terms of $$$ per mile, because AA have the monopoly and it’s a popular route. About 25/50mins, depending on aircraft.
Santo Domingo to Port-au-Prince (Haiti) which is about 5 hours by road takes more than one would think by air (about 45 mins) because they use dreadful old planes, ditto Port-au-Prince - Cap-Haitien, and Port-au-Prince - Port-de-Paix. About 40 mins.
Some inter-island flights in the Caribbean can be very short - I’ve flown between St Vincent and St Lucia - less than 15 mins.
Internal flights in Nicaragua, apart from being stomach churning and hair-raising, are like a bus route - planes from the central town of Siuna stop over in Bonanza and La Rosita (10 minute affairs) en route to Managua. These jungle towns are quite close to each other as the crow flies, but the roads are so bad it takes ages to do it over land. Their landing strips double as baseball pitches.
La Ceiba (mainland Honduras) - Roatan (Honduras Bay Islands) is another quickie (maybe 10 mins).
Speaking of Central America, the international flights hop between capitals and the relatively short distances are covered very quickly, especially in large jets. Guatemala City - Managua can involve stopovers in Tegucigalpa and/or San Salvador (20-30 mins).
I was on my way back to Denver from Phoenix when thunderstorms closed DIA. My plane (737) landed in Colorado Springs, and after waiting an hour or so on the tarmac, we flew the rest of the way to Denver. It is about 60 miles by road, probably around 45 miles as the crow flies. I didn’t time it, but it took me longer to get to the main terminal via the train than it did to fly that leg.
My sister, who went to UC, used to fly Columbus to Raleigh all the time to visit our middle sister. Every flight routed through Cinci. Somehow, it was between $50 and $250 cheaper to fly Columbus->Cincinnati->RDU than to go directly Cinci->RDU.
I’m pretty sure that I flew the Oakland-SF route on United when I was a kid (as part of a longer trip). It used to be the shortest regularly scheduled flight by any major airline, don’t think you can do it as a separate trip these days.
However I used to routinely do much shorter trips - 1-3 miles up, one-way trip (getting out at the top). Shortest ever were the “hop & pop” jumps from 2500 feet on cloudy days. No beverage service on those flights 
As with Qadgop, I’ve flown Chicago to Milwaukee and Milwaukee to Detroit (there was no easy direct flight from Toronto).
I’ve also flown Toronto to Ottawa (60 minute flight) and back in the same day. I had to renew my British passport at the British High Commission there in an emergency.
I’ve flown Toronto to New York (La Guardia, since Toronto has U.S. Customs), which is a 65 minute flight, many, many times. In the '80’s, I worked for a Wall Street firm.