My wife's conference will end in late afternoon in June (weekday). We may fly to Jackson Hole the next morning, out of O'Hare (there are flights out of Midway but with more stops). One option we're considering is moving to the Hilton at O'Hare for the last night, since it costs much less than the conference hotels, and we'd be closer for the 8 a.m. flight. I know the train would be the quickest way at rush hour, but if we each have two suitcases, and carry-on bags, not sure I can convince my wife to go that route (couldn't convince her to take BART from Oakland airport to downtown SF). If we do take a shuttle, how long would it likely take, and cost, at, say 5 or 6 p.m.? Would we be better off having dinner in town and taking the shuttle or taxi about 7:30 or 8?

Thanks!