Lots of factors would go into the decision. For various reasons, most of my travel the past few years has been between Seattle and the Santa Rosa area, so some of the considerations have been:

• Construction at STS that was not at all friendly to those of us with mobility issues (I'm not so bad off that I want to get a wheelchair, but having to walk all the way around the terminal building to get to the temporary baggage claim facility was pushing it).
• Modifications at SEA, combined with a resurgence of traffic post-COVID, that has made that airport a nightmare.
• An expired passport and a non-enhanced driver's license.

Drove the last two years, taking the train this year (which has its own challenges: train to Martinez and an Amtrak bus to Rohnert Park; Airporter bus to SFO for a chance at some dinner, BART to Millbrae, Caltrain to San Jose, Amtrak home -- rather than sit at Martinez for 9 hours after taking the bus there and having a selection of vending machine items for dinner). If my friends are still in condition to have guests by then, I'll likely go back to flying next year.

In older times, it was a lot like the OP's situation. Yeah, it's just a 45-minute flight ORD to IND, but I can be halfway there driving by the time I boarded the plane. CVG was a no-brainer: fly. Even STL, though, was a toss-up, since I lived in the southwest suburbs. I should have driven the time I was going to see a client in Belleville, but flying was right for a visit to St Charles.