LSL, ALB to CHI best side of train end of May.

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Which side of the LSL is best from Albany en route to Chicago at the end of May?

Not sure I understand the question. You are scheduled to depart Albany at 705 pm. Assume you will have daylight by Toledo, 515 AM, and arrive Chicago at 950 AM. So your question concerns the Toledo-Chicago segment? Pretty much either side is ok (there is nothing interesting to view on either side), except maybe the Chicago skyline as you approach it. (The view of the Hudson River from NYC to Albany is great but outside the scope of your question.)
 
Not sure I understand the question. You are scheduled to depart Albany at 705 pm. Assume you will have daylight by Toledo, 515 AM, and arrive Chicago at 950 AM. So your question concerns the Toledo-Chicago segment? Pretty much either side is ok (there is nothing interesting to view on either side), except maybe the Chicago skyline as you approach it. (The view of the Hudson River from NYC to Albany is great but outside the scope of your question.)

I think a 7:05 p.m. departure is ideal to see the beautiful sunset over the Hudson this time of year, from the left side of the train.
 
The OP is leaving from Albany NY and the scheduled departure is 705 pm from Albany. The Hudson will be in the rear view mirror by then. No sunset over the Hudson is visible after Albany traveling westbound on the LSL, as the OP intends to do.
 
On May 31st, sunset in Utica is at 8:33 PM, just 11 minutes before LSL arrival. So if the train is running on time, you should get a pretty good view of the Mohawk River and its valley, on the left side of train, although you might get some glare from the low sun...
 
We’re leaving from Àlbany/Rensselaer. So hopefully we’re gonna get an actual train. Although these days, who knows?
You can be reasonably sure that you will get a real train. The only exception happened to me once when CSX managed to topple over an entire freight train near Herkimer and we were first given a ride in a Coach on a special connecting train from NY to Albany, then a bus bridge to Buffalo Depew, and then onto a real train in the middle of the night. But as is obvious, that is extremely unusual.
 
Thank you all for your replies, comments and suggestions. Our trip was great accomodation wise: roomette #2 in car #4911 (NY portion). The BOS portion was late to arrive in Albany and we got to CHI the morning after around 10:10AM. The only view we really enjoyed was the Mohawk River past Schenectady.

Our sleeper attendant James was very nice and professional. Please tip your attendant. We tipped some at the beginning and some at the end. We ate in the dinning car where only half the tables were available because of the COVID-19 protocol. The BOS portion of the train being at the front of the train, we did not see anybody showing up at the dining car from that part of the train, they probably had their food delivered to their rooms. Our sleeper was right behind the dining car. The food was mediocre both for dinner (pasta and meatballs) and breakfast (egg sandwich). When I got up, I asked our attendant for a coffee and milk, and he made me the best coffee; better than the dining car one which was watered down. Also beware that nor in the sleeper, dinner or cafe, is there any decaf...

We were happy to have our own toilet in our compartment. Some people think it's gross, but I disagree. They're absent from the roomettes in the Superliner Sleepers and the Viewliner II Sleepers, and for this reason, I would save my money and book a bedroom if I'd travel overnight again, especially for a few nights. This being said, I don't intend to take a multi-night trip on Amtrak until this "flexible dining" is abandoned and they go back to made to order food.

Our luggage consisted of two carry-on size suitcases and 2 back packs. Everything fitted in the roomette. There's also a baggage car if you have more luggage. We used the coat hooks on each side to hang our back packs where we kept our essentials. We brought an 8 foot extension cord with 3 outlets and a flat plug ($5.99 at Lowe's) which came in very handy, especially for the upper bunk.

When I used the shower (in the morning), there were only two towels left. Water pressure was ok and temperature so so.

We slept fine and the ride was pretty quiet. When we got to CHI, the weather was warm and beautiful and we had a great time in the windy city.

This train trip cost for 2 was $352.00 including a companion coupon. IMHO, not worth more without full service dining.

BTW, our train was "sold out" both in sleeper and coach accomodations.

Take care everybody and happy train rides!
 
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I've never seen the shower out of towels, except if someone laid a bunch of them on the floor to have a dry changing area. Most (not all) SCA stock the towels pretty well, and hang a bag for wet towels. Just let them know, they will bring more.
This is only my personal experience. And TBH, I did not want to bother our SCA as he was very busy, but that’s on me.
 
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Decaf has always been available? Was on our recent LSL roundtrip.
Good trip report, thanks. How did you get only $352 for two people?? Low bucket for one is $394.
As for the coffee, I asked my SCA, the dinner attendant and walked all the way up to the café car, and nobody had decaf. Where did you get yours from?

Concerning the price, I just double checked my credit card statement, and the one way ride was $352.00, for my partner and I, including a companion coupon. It was purchased around 4/6/21. Does the coupon make a difference?
 
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