Amtrak coaches are comfortable, but their appeal definitely wears off after ten hours or so. Sooner if the train is crowded.

And getting a good night's sleep in a coach seat is next to impossible unless you're under the age of 12.

As for whether to leave from Milwaukee or Chicago:

With a sleeper, it doesn't matter. But if you opt for coach, it might.

Unless the crew decides to assign specific seats, you'll be free to choose your own. Board the train in Chicago and you'll have more choices. Board in Milwaukee, especially during heavy passenger periods, and you could find all the window seats gone.

Coach is fine for one night if you're on a budget, but you probably won't sleep much, especially the first time. (It gets easier the more you do it.) A sleeper is definitely better, though. For trips covering more than one night, definitely get a sleeper.

Sleeper prices for a standard bedroom are pretty good these days, but book early as they often sell out.

Coach seats offer gobs of legroom, and there is plenty of space to recline without putting your seat back in someone's face. You get a leg rest, a foot rest, a fold down tray table and a small airline style pillow.

Food in a sleeper isn't exactly "free." It is included in the sleeper price. It is worth about $30-$40 per day per person. So figure that in when calculating the price difference for sleepers and coach. If you ride coach and take at least some of your meals from the pre-packaged stuff in the lounge cafe, you can save some money, too, but it isn't nearly as good as the freshly cooked meals in the diner.

Following the KISS principle, I suggest you leave from the station nearest your home.

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Trust God, love your neighbor, and never mistake opinion for truth.
-Mr. Toy

The Del Monte Club Car