PSUMarkDC

Due to a change in flight plans for a trip to Milwaukee this October, I've found myself considering Amtrak for our trip since for the two of us it'd be cheaper than airfare that's currently showing on Kayak. I'm down to two options, and I'm wondering which is likely to be the best - and when I say "best" I mean mainly which is more likely to arrive on time (I know, freight trains causing delays, CSX, blah blah) and which is more likely to be a pleasant traveling experience:

Itinerary 1:
--Depart Harrisburg 2:36pm--
43 Pennsylvanian 5h 29m; business class upgrade
--Arrive Pittsburgh 8:05pm, depart 11:55pm--
29 Capitol Limited 9h 45m; reserved coach seat
--Arrive Chicago 8:40am--

PRO: My girlfriend is going to school just south of Harrisburg so it will be more convenient for her if I drive up there and then to the Amtrak station; cheaper fare.
CON: Parking at Harrisburg; almost 4 hours in Pittsburgh between trains...what to do at that time of night?

Itinerary 2:
--Depart Washington 4:05pm--
29 Capitol Limited 17h 35m; reserved coach seat
--Arrive Chicago 8:40am--

PRO: No changing trains; no need to park at the station since we can take Metro from my apartment in Fairfax.
CON: Much longer ride (is it worth it for this length of a trip to spring for the roomette?), more expensive fare.

Obviously, the return trip would be a similar itinerary as well. Any suggestions or advice would be greatly appreciated!

soitgoes

I'd take the Capitol Limited from WAS-CHI and I'd spring for a roomette if the price were reasonable. A roomette will give you lounge access, dinner and breakfast on the train, and, most importantly, a restful night and a shower in the morning. I just picked a random date in October and that worked out to $370 for two people in a roomette (if you luck out on availability, it could be as cheap as $273). AAA, Student Advantage, or ISIC will give you a discount of the railfare portion.

As for arriving on time, both itineraries are equally likely to arrive on time, as the PIT-CHI segment is identical.

Liberty Limited

I second that recommendation. As you are riding in October, the scenery will probably be nice either route you choose (though that slants it towards riding from Harrisburg for the added daylight), but if you can luck up and get the roomette for under $200, it will be pretty much worth it due to the included meals, better sleep, and the shower.

If you opt to ride from Harrisburg, you can stow your luggage at the station, quickly and easily ride down to Station Square from Steel Plaza on "The T" and enjoy a fine dinner there: Grand Concourse if you're splurging (and since you're contemplating this for financial reasons, I assume not) or Joe's Crab Shack or Hooters if you're not!

BobH

Think about taking the "Cap" -- but not from DC, but from Martinsburg, Harper's Ferry, or Cumberland -- or if you go to Harrisburg, think about getting on at the station near the MDT airport.

Bob H

fairviewroad

Not counting the time it takes to get to/from your station of origin, the trip that departs DC is actually 90 minutes shorter, when measured in terms of overall duration. This is because you eliminate the 4 hour layover in PIT. Personally, other factors aside, I'd take the one-seat ride. Keep in mind that the return trip would require you to change trains at 5:30 in the morning in PIT.

fairviewroad

Keep in mind the Pennsylvanian does not stop at Middletown, which is the station I believe Bob H referring to.

The stop closest to Harrisburg to the east is Elizabethtown. For some people this is actually a pretty good option since parking (last I was there) is free. However, since you say your girlfriend is going to school "just south of Harrisburg" (Grantham? Shippensburg?) this would likely require some backtracking. By the time you add in the extra fare and the extra mileage to get there, you will have eaten up a considerable portion of the money you would save on parking.