Work travel in June - the host says they're about the same. I'm not even going to try to CCW during this trip, so would Oakland or SF be a better place to fly in/out of? I'll have followup questions about what to do during that time.

thanks

I always used Oakland since it was faster and cheaper than SFO, while also being closer to where I lived at the time. But that was almost a decade ago. I doubt the situation has changed much, though.

Oakland is probably better, but not by much.  Traffic on the San Francisco side is usually poor most of the time.  While dropping south from Oakland you have some fair alternative once you get to San Jose and the 101 it's the same route.

Both airports are on the south sides of the named cities, away from the less savory areas.

San Jose airport not an option?

when I'm traveling, going to San Jose bumps the rates by about $240. cheaper to do a rental.

How much is your time worth?

With absolutely no traffic, it is 1:40 from San Francisco airport to Monterey, 1:37 from Oakland, and 1:10 from San Jose.

But this is the bay area.  "Absolutely no traffic" rarely happens.

In practice, rush hour traffic (in particular in the evening, when many people try to go home, to cheaper housing south of the bay area) will add roughly an hour to the trip from SFO or OAK, but less than 1/2 hour from San Jose.  The trip from Oakland will be particularly gnarly, since the 880 and 680 in the east bay will be clogged in strange and unpredictable ways.  Now you are comparing 2-1/2 hours to 1-1/2 hours.  Why?  Because San Jose is already pretty far south, and from there to Monterey you have two options (101 south to 156, or 17 south to Santa Cruz and then 1 along the coast), and even a detour via 87 and 85 if things clog on 101.

Specially beware of Saturday mornings and Sunday evenings, when everyone in the bay area tries to go to the coast and back.  We call it "beach traffic".

By the way, Monterey does have an airport with regularly scheduled service.  Flights might be a bit expensive.

Oakland. It's a smaller airport and less chaotic. I've lived in the Bay Area my entire life, and have only use SFO less than 5 times.