Max, three days after surgery, I skipped the Oxycodone, drove to my therapist's office, and ran a couple of errands. I definitely needed to nap and rest after that evolution!
Exactly two weeks after my surgery, I drove about ninety minutes to my first day of work. I was quite comfortable.
BUT work itself was a different story. I had been prepping all the previous day--lots of activity from the computer to the couch to the computer to the bookshelf to the couch to the...you get the picture. And I got about four hours of sleep when I needed maybe ten. When I arrived on campus, I had to walk to my office, walk to the department, stand around at the copier, check my mailbox, go back to my office, walk to class, move around in class, etc. That's when I started bleeding.
In short, I think that the driving was the easy part. Even the drive home was pretty much a piece of cake after all of that moving around. I made one stop (for maxipads) and then rested all day. I was physically tired, and I was emotionally strung out because I was worried about bleeding. But driving wasn't really a problem.
Okay, that's three hours of self-driving and about three hours of various forms of light physical activity after a full day of prepping and too little sleep. I left the house a little before 10:00 a.m. and arrived home a little before 4:00 p.m. I don't know how my experience stacks up against what you are planning. Does it seem equivalent? How long is the flight from Chicago to D.C.? You can definitely improve your situation by sleeping a lot and taking it easy beforehand AND afterward. Perhaps you can hire transportation? At least you seem to be considerably younger than I.
But it still sounds like a lot from where I am sitting. If I were you, I'd lay everything out and ask the surgeon if that sounds like too much at the two-week window.