I've done it a few times.

Back when AA NetsAAver fares were actually legit deals, three friends and I would pick a weekend and agree that we're going to travel somewhere just for kicks for 3 nights. When the deals dropped on Tuesday, we'd gather for beers and make our pick. Sometimes it was obvious; sometimes it involved debate and occasionally just flipping a coin. One time ORD-MXP was by far the best deal, so we did it not having a single clue what our itinerary would be when we got there. Ended up being a fantastic weekend that still gets brought up in conversation from time to time almost 20 years later...

Did probably a dozen of these (ex-ORD) over the course of 3 years before everybody was on the Internet and NetsAAvers got lame.