Ok Dana, so the cheapest Oakland flight that works best for me is $264. Not bad, wish it could be cheaper, but it's better than $300. Leaves O'Hare at 6:15am, stop over in Dallas, arrives Oakland at 11:30am. Return flight leaves at 1:30 pm, arrives home (with another stop in Dallas) at 10 pm. Sound good? If so, I'll book this flight tonight. I found a site that shows a line graph of ticket sales. If we booked our tickets 2 months ago to the day, they would've been $200. Oh well, can't win every time.
I'll pay a little extra if it means we don't have to wake up at the crack of dawn to leave, y'know?
Ok, so I went to a different website called farecast.com that gives you lowest fare predictions. They say to wait because the prices will drop about $38 ... they say it's a 70% chance they will. Might be ok to wait a day or two, not get it on the weekend and such.