I took the train from Oakland to NYC 20 or so years ago. I wouldn’t do that again, because I apparently can’t sleep on a moving train no matter how tired I am. But I will say that the trip from California to Chicago was more or less comfortable and the scenery almost always beautiful; however, the train from Chicago to New York was smaller, shakier, much less comfortable, and the scenery was an unguided tour of the ass-end of every misbegotten Rust Belt city in Indiana, Ohio, and New York, and after a while I got tired of counting refrigerators and shopping carts that had been dumped down ravines next to the tracks. And to top it off I sat on the tracks outside of Albany for 3 hours. I would be a lot more enthusiastic about repeating the western part of the trip than the eastern one.
Thanks for all these suggestions guys – I’m taking notes!
one thought – Southwest does not have a markup for one-way flights, and IIRC one-way tickets on AmTrak are also reasonable, so you could fly one way and take the train the other, so you’re not committed to 40-50 hours on the train. Just an idea.
I did a thirteen hour train ride with my two little boys last summer and it was fantastic. Eight billion times better than the plane. Small stations so we had to walk about thirty feet from our car to the door, no security hassle, friendly staff, friendly passengers - everything was very low-key and low-stress. We got a sleeper car with two bunks and it had a door that locked, its own toilet & sink, and a little table. We just chilled out, watched the scenery go by, and I read books to them. With the kids it was great, because I didn’t have to worry about them wiggling and making a little noise - since had our own room, there was no way anyone could hear us. We slept well, then woke up and had a sit-down breakfast in the dining car. I’d do it again in a heartbeat. I’d really like to do a trip like that alone because it would be hours and hours of blissful knitting and listening to audiobooks.
Go for it. It’ll be an experience you will never forget (for better or for worse!) One 4th of July I took a train from Boston to Albany, changed for Toronto, hoteled overnight, CN train to Winnipeg, changed trains for side trip on the Greater Winnepeg Waterworks RR (because it was there), took prearranged (incredulous) cab back to station, train to Calgary and Saskatoon (went thru Hornepayne somewhere-we pronounced it horny pain) to Jasper, BC. Overnighted there, ran into, quite by chance, the “mayor” of my hometown and his wife who were train tripping the continent clockwise.
We 4 rented a car and drove to Banff, sidetripping onto the Columbia Icefield, back to Jasper, train up to Prince George,BC. Changed trains to the self-propelled Budd cars and trained down the Fraser River Valley to Vancouver, with meals served on a tray on a lap pillow because of the swaying. Overnighted in V, visited Simon Fraser U, Queen Elizabeth Park, walked across the Lion’s Gate(?) bridge, took the cable car up the mountain.
Train to Seattle, met some Danish chicks there, overnighted, rode the monorail to the space needle. Drove in a the chicks’ rented VW bug to Portland. Overnighted. Chicks went to Mt. Lassen volcano. We rented a car there due to lousy overnight train skeds and drove to SF, stopping at Willits to ride the Skunk Train to/from Fort Bragg where we touched the Pacific Ocean for the first and last time. Overnighted in SF. Then took the California Zephyr to Denver (at sundown) and Chicago (first time there). Overnighted.
I was train-pooped so I flew back to Boston. Railbuff companion took the train. 9,000 miles in 16 days. I’d do it again if I had the time and if the skeds permitted.
Heh. I read that article in the paper Onion, sitting in a waiting area to get on a United flight from Austin to San Jose. I wondered when the Onion switched from satire to straight news reporting. 
I can’t read in cars at all, but I’ve never had a problem on a train.
BTW, Union Station in DC is a great place. (Or it was 15 years ago.) When I went to meetings in DC I’d hang out there waiting for my train to Trenton. Lots of good restaurants and a nice mall to let you while away the time. And if you have enough time to go out, no security line to get back in.
I’m taking a train on the 15th to New York to interview someone for a freelance job. I could have gotten a plane ticket and been there in three hours but I deliberately took the train because I enjoyed the experience so much last time. It’ll be 21 hours each way. I got a private room for the ride back.
I liked it a lot the last time I rode the Cardinal. I saw some interesting scenery, and the seats were pretty comfortable; so was the sleeper. There were plenty of outlets for my laptop.
The coach seats on a train are about the same as a first class seat on a plane. As far as I’m concerned, the train beats flying unless you’re flying on a luxury plane designed for comfort.
IME Amtrak base fares are usually a lot lower than the lowest airfare you can reasonably get. Where it can run into money is in buying meals, if you want to use the dining car, or in sleeping accommodations. You never have to pay for both a roomette and meals, because all meals are included with the room. Once I researched fares with accommodation from L.A. to N.Y. and found the cost to be about $1500 round trip, per person. On the other hand, my wife and I once traveled by train from Seattle to L.A., with sleeper, at a total cost of $430. I don’t think we could have gotten one-way plane tickets for that.
I traveled by train from Lancaster, PA to Chicago, several years ago. It was a straight trip on the Broadway Limited. Since it was an 18 hour trip, I got a sleeper (lower on the way out, upper on the way back) which also had a toilet and sink. Lots of fun! You would probably enjoy yourself more and rest better with a sleeper.
Oops! Forgot: Maybe you could go Philly to Lancaster to Chicago, or Philly straight through to Chicago.
Can’t second this enough. I’d MUCH rather take Amtrak than fly or take a bus; its downright pleasant.
Not to, uh, encourage drug abuse, but for long air trips, an Ambien or similar is a magic bullet. Don’t even think about drinking with it.
I may have an unused bottle of those around here somewhere.
Another train buff here - absolutely, I’d take the train trip. It would be worth asking if there are sleeper cars or roomettes, but even if the large recliner seats are all that are on offer, I’d much rather take a train than fly, bus or drive.
I think the OP could probably do better by first going to NYC and then taking the Lakeshore Limited to Chicago.
I took Amtrak from Los angeles to New York City in November 2008. We started with a “roomette” (that was 2 small chairs, fold down table, and a toilet that you could barely fit on)…when I knew I was going to be with that for the whole trip we asked to be upgraded to the bigger room with a bathroom and sink and actual space to get dressed in.
I liked the travel on Amtrak…loved the flat iron steak. You get breakfast, lunch, and dinnr if you have a room. It was fun trying to take a shower on the train. The shower was the actual bathroom with a shower curtain to close over the door. It’s very claustrophobic. I barely fit in the shower because I’m big…but not really super huge. If you dropped the soap you had to open the door to bend over. The drain in the shower got plugged and it flooded my room, so we had to change rooms going from Chicago to LA.
I liked the scenery, especially the snow. I’ve enever seen it snow in my life, and when I stepped out for a break in Utica, New York it was snowing. I got it on video. It wa awesome. If you’re travelling with someone make sure you can tolerate them, and cramped spaces. Be open to meeting new people when you dine, and move over for them to pass through the hallways.
I think it would make almost no difference. Lakeshore Ltd is a 19hr straight shot from NYC to Chicago. It will take a couple of hours to get to NYC from Philadelphia. It’s a wash in the end.
can’t you get a sleeping car? IIRC, they weren’t that expensive, and I loved it. I could’ve ridden for a week with a sleeping car.