I agree with you, that Amtrak's site could be a LOT more user friendly to those considering an Amtrak train ride for their first time. That's for sure! Do have no doubt that the lack of user friendliness to those new to riding Amtrak, probably has discouraged at least a few new riders from considering riding Amtrak as quickly for their first time.
Anyway, this is Amtrak's system map:
https://www.amtrak.com/content/dam/...lic/documents/Maps/Amtrak-System-Map-1018.pdf (pdf)
https://www.amtrak.com/plan-your-trip.html (interactive map, this one is GREAT if you're trying to figure out all the small towns, state and national parks, etc. that the train runs near. honestly if not for this map, I wouldn't have realized the Empire Builder train runs RIGHT NEXT TO the Fort Union Trading Post(a historic Native American fur trading post), in western North Dakota west of Williston)
It looks like per the pdf map I saw and linked to above, that there allegedly at least at one time was thruway bus service between Davenport and Galesburg. Sadly a search I tried doing on Amtrak's website when I did a pretend booking of Davenport to Rutland, showed no bus service between Davenport and Galesburg. Am not sure if any other bus companies do run bus service between Davenport and Galesburg, so keep in mind I am not sure if you'd have to drive south to Galesburg to catch the train. Also that is a good question I'm thinking in my mind, if Galesburg, IL does have any long term parking? That is if you chose to drive yourself to the station, to board an Amtrak train between Galesburg to Rutland.
So with looking at Amtrak's reservation system not coming up with any results for a thruway bus between Davenport and Galesburg(so you'd have to find some way to travel south to Galesburg to catch the train), I at least did correctly figured out(like I assumed all along) that a train trip between Galesburg to Rutland is possible. You would take train #4, the *Southwest Chief(arriving at 11:48am going east) towards Chicago, then once in Chicago you'd transfer to the Lake Shore Limited(leaves Chicago at 9:30pm, so you'll have a little bit of a layover to do some things in Chicago for fun during that time, 2:50pm to 9:30pm). I will advise the food court options within Chicago Union Station can IMO be a little meh(except Jersey Mike's and Starbucks), so if you are LUCKY enough to be arriving into Chicago on a weekday, I'd recommend walking a few blocks east to Revival Food Hall, and get a good meal there(
https://www.revivalfoodhall.com/all-vendors , for a list of all locally owned places that do have a stand at Revival). If you more just want to go to a bar with good bar type food, you could walk to Dylan's Tavern a few blocks away(
https://www.yelp.com/biz/dylans-tavern-and-grill-chicago ). Also in this area near Dylan's there are a lot of various places one could eat at which aren't too expensive(i.e. Blaze Pizza, Blackwood BBQ, list goes on and on), and also Ogilvie Transit Center(which is a train hub for 3 Metra lines) has a food court with Popeye's, Taco Bell, Arby's, and several other options.
Keep in mind since you'd transfer to the Ethan Allen Express(your 3rd and final Amtrak train to Rutland) upon arriving in Schenectady, that your reservation will book you onto one half of the Lake Shore Limited train(going to either New York City, or Boston). This train runs as a combined train between Chicago and Albany-Rensselaer, and east of there the train splits into two halves, or is combined there for going west. If you're in any cars of the Lake Shore Limited going towards NYC your ticket will show train #48 for the Lake Shore Limited, and if it's in any of the cars assigned to go to Boston, it will show train #448. I would use the fact you see 2 different fares for train #48 or train #448 to your advantage, since it means one half of that train may at times show a slightly cheaper train fare.
Anyway on day 2 after you've ridden the Lake Shore Limited(combined train #48/#448) east into Schenectady, that you'd have a layover there between 1:53pm and 5:28pm. At 5:28pm, is when your northbound train #291(Ethan Allen Express) will arrive into Schenectady, NY, and you'd take that train all the way north to that train's final stop, in Rutland, VT. Going back to Chicago, you would book southbound Ethan Allen Express train #290 leaving Rutland at 8:15am, arrive at Schnectady at 10:28am for a **LONG layover there(9 hours, dang!) till your next train arrives at 7:33pm(Lake Shore Limited, train #49/#449). From there you take that train west to Chicago(arriving at 9:50am on day 2), and then you could take the California Zephyr(train #5) west from Chicago(leaves at 2pm) to Galesburg, where it finally arrives at 4:38pm. And from there, you'd of course drive back to Davenport from there, or either see if any intercity bus service existed between Galesburg and Davenport(who knows about that) or get a ride from someone else north from Galesburg to Davenport.
I'm sure such a train trip will go well for you, and enjoy your trip! Also I COULD HAVE SWORN that this post already went through and is on this thread here, but weirdly it didn't post yet. I am VERY darn thankful that this site saves posts, otherwise all this very useful info would've been lost(ugh).
*- Since Southwest Chief train #4 is coming in all the way from when it started 2 days earlier in LA, there always is a limited off chance this train could be 1-3 hours late arriving into Galesburg. Luckily for you out of several long distance train routes running east into Chicago, the Southwest Chief has fewer train delays vs. a lot of other Amtrak trains running east into Chicago(i.e. eastbound train #6, California Zephyr, is worser for sure). The average delay according to juckins.net is 1 hour and 56 minutes arriving into Galesburg, and the median delay is 1 hour and 20 minutes(all train delay data is shown here:
https://juckins.net/amtrak_status/archive/html/historychart.php?train_num=4&station=gbb&date_start=01/01/2019&date_end=12/11/2019&sort=d_dp&chartsize=2&smooth=0 ). You also could look up train delay data btw on this site, for any other train station and respective train you're traveling on. As long as you first figure out the 3 letter code for the station(s) you're interested in, besides also the train number(s).
**- With the layover in Schnectady, NY being like 9 hours, I myself would almost want to consider transferring at a different city, where one would have more things to do during that layover. For example you could travel one station south to Albany-Rensselaer, and do your layover there between the southbound #290 Ethan Allen and westbound #49/449 Lake Shore.
