Why not book an open jaw R/T ticket, Los Angeles-Lisbon-Madrid (or Barcelona)? The round trip cost, in mid-October (LAX-LIS-MAD), is around $1250 USD using United/TAP.

Yes usually if the same airline serves both cities you can book an open-jaw for about the same price as round trip. And I'd suggest Lisbon and Barcelona, a more interesting city than Madrid IMO.

And my next question was going to be: Madrid or Barcelona? So one point for Barcelona so far.

Thanks for the open jaw suggestion! I hadn't even thought of that.

At least you realized the multi-city option before buying the ticket. Even though almost all the booking sites offer round-trip/one-way/multi-city as three options if one goes beyond the quick booking pages, many new comers look at two one-way fares, freak out, buy round-trip fares to inconvenient airports, and freak out again when they come here to find out that they could have bought multi-city flights at similar cost.

For what it's worth, my pick would be Madrid over Barcelona, but both are great places.

We're doing a Madrid-Lisbon trip in October. Flying to Madrid, staying two nights, driving to Salamanca for a one-night stay, then driving to Lisbon for three nights. Then one night at Caceres on our way back to Madrid, where we will stay another two nights. I know that's more driving and moving around than most people would prefer, but ee've done similar trips before, and we quite like it.

I'm not sure where my brain was this morning when I was looking at flights; good thing I posted here for help and was reminded of open jaw. It just went completely over my head even though I'd done open jaw/multi-city previously.

I've asked a few friends who've traveled to Spain and it seems like a split opinion right now between Madrid and Barcelona. I suppose I could try to extend my trip a few days and potentially do all three places. My goals for this trip would be to enjoy history, culture, and architecture and eat great local cuisine.

Fly into Lisbon, train to Madrid, and leave from Madrid. In both Lisbon and Madrid you have the possibility of day trips to interesting places. Barcelona is a secondary city and, for us, just doesn't cut it.

Barcelona is fantastic.
You can fly vuling
Lisbon .-Barcelona ..cheap

vueling

There is no way to say which city, Madrid or Barcelona, will be "better" for you.
Both tick all the boxes you mentioned, and the only way to find out is to go there
If you were a big time museum lover, then Madrid would score a few points more than Madrid.
But for a first time visitor, you actually can't go totally wrong either way.
While Vueling usually has attractive fares for LIS-BCN you may also want to check the competitors as well. Whichbudget.com is a good site for comparisons.
I would not have guessed it but for my flight next month, Portugal's legacy airline TAP turned out to be the cheapest option to go from Barcelona to Lisbon for €45 o/w, taxes, fees, and one 20kg bag checked luggage included.

Taking is the train from Lisbon to Madrid may be interesting, but the flight is much quicker and more comfortable, at least until they put on the high speed train (sometime in the distant future).

Taking Vueling's flight from Lisbon to Madrid or Barcelona means that you would not be able to book one ticket unless you had a travel agent make the flight arrangements, and it would end up costing more.

why cannot a person book a vueling ticket on the Net?
We have not used a travel agent to book flights , hotels, train tickets etc in years.