Is this best done via Amtrak or Canadian Rail. Amtrak has such a bad reputation. What are the roomettes like?

Amtrak runs trains in the US, Canadian Rail runs trains in Canada. Neither runs trains between those cities.

That's true. I prefer Via Rail, because they have one person roomettes with toilets, and slightly better food. But the food on the long distance Amtrak trains is surprisingly good. Singles on Amtrak trains have to pay for a double roomette if they want a sleeper.

Not true. You can take the Empire Builder to Seattle and the Cascades to Vancouver. Sometimes the Cascades is a bus and sometimes it's a train. Or you can take the California Zephyr to San Francisco and the Coast Starlight to Seattle. I had an enjoyable trip on the California Zephyr a few years back: https://mytimetotravel.wordpress.com...fornia-zephyr/

If you want to use Via Rail you'd need to get to Toronto first.

Of course you can piece together a rail journey between Chicago and Vancouver.

What you can't do is get on a train in Chicago, and get off that same train in Vancouver, which is what the OP seems to want to do.

I doubt that the people that give Amtrak a bad review have ever ridden Amtrak long distance trains more than 2000 miles. In the past month I've ridden Amtrak more than 4000 miles and will be taking another long Amtrak trip next month.
If you are starting the trip from Chicago, your best choice is to take the Empire Builder to Seattle (train splits in Spokane other half to Portland). From Seattle, there are several Amtrak buses that leave King St. station to Vancouver and 2 daily Cascades trains to Vancouver.
Unless you can find a way to get to Winnipeg from Chicago to get on the ViaRail Canadian, it would not be wise to try riding the Canadian. The Canadian only runs 2 or 3 times a week from Toronto to Vancouver.
It is a beautiful trip through the Canadian Rockies, but i doubt that I will ever ride it again.

Hi,

Having taking the Empire Builder train from Chicago to Seattle via Roomette and the Canadian train from Toronto to Vancouver in a berth on more than one occasion, these are my thoughts: The Canadian ride is a good bit more expensive, however, it can be quite a fun experience, with often entertainers, an activities coordinator, a bar car, a dome car where one can observe scenery from a higher vantage point as well as a games car. The dining is a delight, emphasizing food from the provinces being passed through. Amtrak tries though (with bad ideas occasionally like replacing sit-down dinners with box suppers on the Capitol Limited from DC to Chicago) and while on the Empire Builder, there have been wine & cheese tastings. There is a car that has panoramic windows. I find the roomette fine on Amtrak and have slept well in it although some find it too cramped or awkward. Both trains have stunning scenery beginning western Montana/western Alberta and moving westward.

Starting from Chicago heading west, Amtrak to Seattle is your best option, unless you wanted to fly somewhere in Canada or had extra time to drive to Winnipeg or rail to Toronto (I've taken the train from Chicago, combined with a bus to Toronto; it's do-able but probably not many people's idea of fun (I had fun but I'm weird lol)).

Best wishes,

Daniel