I'm going to being doing both the CS and EB in one trip the last of Oct through first week of Nov, so if you choose the EB, we might connect. In my case, I will fly WAS (DCA) to LAX, and spend time in Hollywood before heading north on the CS to Seattle. From Seattle, we're on the EB to MKE, where we will overnight before returning to WAS via air.
The CS is obviously a wonderful experience, with the Pacific coast and the Parlour Car with those great swivel chairs, a big window, and a glass of wine. But if you really want to enjoy a long haul (and a couple of nights) on Amtrak, then it is the EB, CZ, SC, or TE. Of those, in many respects, I find the EB may be the most "elegant." [Forum, please feel free to weigh in and disagree. Which of those 4 do you like the best?] The wine tasting and real porcelain for eating add a little bit of that elegance, available on the EB, but not on the other long hauls. Last April, we were on board westbound on the EB with Manny as our attendant on his 3rd to last trip before retiring, so that made it even more fun. Luckily, we made it one day before the Red River went a little too much into flood stage. But I got some great picture of prairie potholes full of water, and it was pretty cool seeing us on the railroad bed surrounded by water on both sides along the way.
Like you, we want to do this trip before the snow flies, and see North Dakota while it is brown and not white. After all, why not Minot in November? We are preparing for possible delays, however, realizing the recent 15-hour delay that the EB had eastbound from Stanley. So, we will overnight in MKE before flying home, probably heading to the Wisconsin Cheese Store to clog our arteries before leaving.
So, should you head east to CHI? Two hours of delay is cutting it pretty close. But… With the current budget climate in Washington, you might want to start thinking about what to ride on Amtrak in terms of potential budget cuts to Amtrak. As we have had in several forum discussions, there has been much speculation about possible route cuts. As one who lives inside the DC Beltway and keeps an eye on these things, I am not real optimistic about the future of Amtrak maintaining everything it now does. (Or a lot of other parts of government for that matter). The CS might survive, but I wonder if all 4 long hauls will. In our case, we'll do the EB (and the CS) in Oct-Nov. Then, in December, we'll fly back west to jump on board the SL and the catch the Crescent back to WAS. At that time, the southern route of the four long hauls is where the weather should be a little warmer. But early November should be doable (high probability anyway) on the northern EB route.
So if you are a little pessimistic about survival of the long hauls, you might want to choose the EB instead of the CS. Let us know what you do. If you don't make the EB, I'll let you know how we did on it in that same time-frame you are thinking.