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Chicago to Alaska: Rail & Sail Adventure

Chicago to Alaska Rail & Sail Adventure (Part 1 of 4)

Chicago - Syracuse - Toronto - Jasper - Prince Rupert - Sitka

By Robert & Kandace Tabern, Email:

Published: November 1, 2017

The above map shows our "Rail & Sail" journey that we took from Chicago, Illinois to Sitka, Alaska between September 9-18, 2017. Red marks the Amtrak "Lake Shore Limited" route we took from Chicago to Syracuse, New York; orange marks the Amtrak/VIA "Maple Leaf" route we took from Syracuse to Toronto, Ontario; yellow marks the VIA "Canadian" route from Toronto to Jasper, Alberta; green marks the VIA "Skeena" route from Jasper to Prince Rupert, British Columbia; and, finally, blue marks the route of the Alaska State Ferry we took Prince Rupert to Sitka, Alaska.

This article will be presented in the following four parts:

../index%20photos/trip-RailToAlaska12017.jpg Part One: Chicago to Toronto (Will be uploaded on November 1, 2017)
../index%20photos/trip-RailToAlaska22017.jpg Part Two: Toronto to Jasper (Will be uploaded on November 15, 2017)
../index%20photos/trip-RailToAlaska32017.jpg Part Three: Jasper to Prince Rupert (Will be uploaded on December 1, 2017)
../index%20photos/trip-RailToAlaska42017.jpg Part Four: Prince Rupert to Sitka (Will be uploaded on December 15, 2017)

Over the next six weeks or so we will be posting a series of four articles here on TrainWeb about how you can take the train from Chicago to almost Alaska (well, just short of Alaska – Prince Rupert, British Columbia to be exact, which is just a four hour ferry ride to our “Last Frontier”). A lot of people who aren't travel savvy probably don’t even know something like this is even possible – so we are glad to be sharing this experience with you exclusively here on the main page of TrainWeb. How did the trip work in a nutshell? From Chicago Union Station to Syracuse, New York we took Amtrak’s Lake Shore Limited.  From Syracuse, New York to Toronto, Ontario we took Amtrak/VIA’s Maple Leaf train. Then it was onward between Toronto and Jasper on VIA’s Canadian.  Our final train was VIA Train #5 (formerly known as the Skeena) between Jasper and Prince George and Prince Rupert. Then it was the Alaska Ferry for a little over one day (and one night) to Sitka, Alaska before heading home on the plane (one only gets so much vacation time!).

Our journey began at Chicago Union Station on Friday, September 8, 2017 at 9:30pm Central Time with the departure of Amtrak’s Lake Shore Limited. This train features two sections – one that operates from Chicago to Boston, Massachusetts (Train #448) – and the other one which operates from Chicago to New York City – Penn Station, New York (Train #48). Between Chicago and Albany, NY the two sections of the train run together as one train. Typically, two Viewliner sleepers on this train operate to New York City and one Viewliner sleeper operates to Boston. When booking, we chose the Boston section of the train because we heard it was the quieter option (being further from the dining car and most of the coaches). On our travel date, we found out the entire train would be running through to New York Penn Station due to track work at Albany, NY. Those who were going to Boston would have to get off at Albany and take an all-coach stub train (no thru sleeper service we happening during the Albany track work). 

We started our evening out at the Metropolitan Lounge at Chicago Union Station. Robert went to Beggar’s Pizza across the street from the station and got some Chicago deep dish pizza and Kandace enjoyed a chef’s salad. Hurricane Irma was a few days away from hitting South Florida at this point, so we were pretty glued to the TV’s showing storm preps until around departure time was called.

All Aboard!  Our journey begins at Chicago Union Station on September 8, 2017 with the departure of the Lake Shore Limited

Because of the track work mentioned earlier at Albany, all three sleeping cars were actually placed together in the consist at the rear of the train. Departing Chicago going east, the Lake Shore Limited once featured a full dinner, then downgraded to a snack of wine and cheese, but service has now been cut back to no food service what-so-ever (except for cafe car options which is open until 11PM). It wasn’t needed really anyway with the great meal options available in Downtown Chicago. I'll take deep dish pizza from an oven over microwaved cafe car DiGiorno's anytime! We boarded around 8:45pm and had time to get some photos of the platform and train cars before departure. Since we were going to just be on this train for one night, we decided to travel in the Viewliner Roomette. From what we heard, Amtrak is in the process of re-designing these rooms and removing the toilet. Having a toilet in the economy bedroom is great for one person, but it can present some awkward situations for two travelers – especially in the middle of the night!  Robert took the upper bunk and Kandace took the lower bunk. We watched Chicago fade away as we talked about what we would be looking forward to ahead during our 5,000-mile train trip to just shy of the Alaska border.  Somewhere in Northwest Indiana we decided to call it a night and lights out.

Our trek between Chicago and Alaska begins walking out to the Lake Shore Limited at Chicago Union Station

Robert gets pictures of the train before its departure from Chicago, while Kandace reads a book inside our Viewliner roomette

We woke up the next morning (Saturday, September 9th, 2017) and the Lake Shore Limited was between Erie, PA and Buffalo, NY already. We both slept really good having worked the entire day prior, as not to burn up too much vacation time from our employers. We decided to head down to the dining car for breakfast shortly after waking up. Until recently, the Lake Shore Limited featured a full heritage dining car.  Most of the cars were either the CB&Q or the Pennsylvania Railroad and dated to the 1940’s and 1950’s.  Due to maintenance issues and the fact new Viewliner dining cars are being built, Amtrak decided to temporarily use Amfleet café cars for dining cars on the Lake Shore Limited until new Viewliner Diners could be completed.  The same kind of car is used on the Cardinal, just with slightly better food selections.  The remaining heritage dining cars are still used on the Silver Meteor (New York to Miami) and Crescent (New York to New Orleans) trains.  We ended up having some French toast which was actually pretty decent given that it was done in the convection oven. It sure beat the "omelet" on the Cardinal, which seemed to be the equivalent of a McDonald's egg patty.

From there, it was back to the our Viewliner roomette as we watched some of the Upstate New York countryside glide by outside our window. Having traveled extensively, it’s always funny to think that most people picture New York City when they think of New York – yet often forget that NYC is just sliver of the State of New York. Most of the state is farms, rural countryside, and mountains.

For this particular journey, we decided to ride the Lake Shore Limited through to Syracuse. This would allow us a 90 minute connection time there until we caught the Maple Leaf back west to Buffalo, Niagara Falls, and eventually Toronto (to make our connection that evening with the Canadian).  We could have de-trained in Buffalo on the Lake Shore if we really wanted more time there --- but that would have allowed us way too much time just to sit around the station. We talked about getting off in Buffalo and renting a car to do some sightseeing, but didn’t want anything to happen and make us miss our connection to the Maple Leaf.

A brief "fresh air stop" on the Lake Shore Limited at Buffalo, New York on the morning of Saturday, September 8, 2017

Kandace says 'goodbye' to the Lake Shore Limited at Syracuse, New York; we will wait for the Maple Leaf, but the train will continue east to Boston and New York City

We arrived just a few minutes late into Syracuse – it’s a nice station there. It’s an intermodal station that features several restaurants like Subway and a convenience store and shares space with Greyhound. While waiting for the westbound Maple Leaf, we got a call from our friend Mike, who was planning on riding the Canadian with us from Toronto to Jasper; he would continue on to Vancouver and we would get off the train in Jasper and make the connection to the train to Prince Rupert. Anyway, Mike flew from Boston to Toronto on Porter Airlines and was already at Toronto Union Station by the time we were still in Syracuse. He dropped the bomb shell that the inbound equipment for the Canadian would be around 10 hours late – and this would mean our outbound train leaving (by the time it was serviced) would likely be somewhere between 1:00am and 3:00am.  Mike was also informed that VIA expected heavy freight traffic for our westbound journey, too, and that would put us in significant delayed to Jasper (us) and Vancouver (Mike).  Mike talked with VIA personnel at the station and advised them he had about 10 hours to spare in Vancouver between his arrival and his flight home – and they told him that might be pushing it.  Mike had to be home on the evening after the Canadian arrived for a concert he had expensive tickets to.  In the end, sadly, Mike decided to scrap the run once he learned he could get his money back.  Maybe another time?  So it would just be us solo.  (Sadly, the Canadian ended up being less than 30 minutes late into Vancouver and he would of had plenty of time to make his connection.)

The westbound Maple Leaf arrived pretty much on time in Syracuse and we made our way to the Business Class section of the train where we had booked.  Business Class on the New York trains must be a popular thing – as we were the last two empty seats available. Unfortunately the only open seats were two singles that we not connected. We decided to put our stuff down and sit in the café car instead since we would not sit together. Since we had just seen the same scenery between Syracuse and Buffalo, we decided to sit in the café and discuss some plans for an upcoming trip to Europe we plans for in May 2018.

One thing that you might find interesting is that you can NOT book an Amtrak Guest Rewards reservations on the Maple Leaf from New York to Toronto. This is because it's technically a VIA train from Niagara Falls, Ontario to Toronto, Ontario -- and hence -- no Amtrak Guest Rewards. What you can do is book an Amtrak Guest Rewards ticket from New York to Niagara Falls, New York and then a paid ticket from Niagara Falls, NY to Toronto. This is what we did -- an Amtrak Guest Rewards redemption from Syracuse, New York to Niagara Falls, New York and then a paid ticket from there to Toronto.  This move actually generated THREE tickets for each person -- or SIX tickets total -- and just confused the heck out of the conductors.  We had one ticket from Syracuse to Niagara Falls, NY (which was the Amtrak Guest Rewards ticket), one ticket from Niagara Falls, NY to the Canadian Border, and then a third ticket from the Canadian Border to Toronto.  The Amtrak conductors took all 3 tickets, but I guess really should have just collected the first two tickets and then the VIA conductor should have collected the last one.  I guess a lot of people don't realize -- or don't do -- what we did here.

The conductor points to us and poses for a photo as the Maple Leaf arrives into Syracuse Station about 90 minutes after the Lake Shore dropped us off there

Our Business Class seats on the Maple Leaf -- we finally asked permission to flip the single seats around so we could sit together; totally sold out business class that day!

Our last photo in the United States - a quick "fresh air stop" at Niagara Falls, New York

Just after Buffalo, the conductor made announcements concerning how the border crossing was going to work. This was something we were curious about and had seen little detail about when booking our tickets or on the Amtrak and VIA websites. Around Buffalo, the conductor came through the train and began passing out forms for everyone who would be going into Canada. It was basic information and covered names, etc. Shortly after filling this out, the train made a stop at Niagara Falls, New York and everyone was given a few minutes on the platform to get some fresh air. From there, we rolled across the stunning bridge over the Niagara Gorge and left the United States behind for the next week.  When we arrived just after the bridge at Niagara Falls’ VIA station, the Amtrak personnel announced they would be getting off the train and VIA personnel would be getting on. Even the café car would be switching from Amtrak to VIA for the remainder of our trip to Toronto. We were also instructed that we would have to get off the train (along with our luggage) and go through customs which was attached to the Niagara Falls VIA station. The train would remain in place at the station and would be “swept” by Canada immigration and that we would be allowed to re-board when everyone was processed.  There were not actually a lot of passengers going through from the USA to Canada and it went very smoothly.

There doesn't appear to be much consistency when it comes to crossing the border on Amtrak. When you cross the border on the Adirondack near Rouses Point, New York, you stay on the train and the border guards come aboard and interview you. Here, though, we had to get off the train.  Believe it or not, this was our first time ever crossing the international border on Amtrak. We have never rode the Cascades
north of Seattle, got off in Rouses Point, NY when riding the Adirondack, and were just not as much into riding trains when the thru-train from Chicago to Toronto was operating.

Our first station stop in Canada - Niagara Falls, Ontario

The train crosses this high gorge between Niagara Falls, New York and Niagara Falls, Ontario. The international border runs right down the middle of the river here.

We re-boarded the Maple Leaf and had an on-time departure at 5:45pm. We went to check out the new set-up in the café car. All of the products were Canadian – and they even had Aero Bars – one of our favorite Canadian chocolates!  We settled for one of those and a cheese and fruit box to tide us over for an early dinner.  Having rode Amtrak a lot, it was weird to see a VIA set-up in the café car on an Amtrak train set.

Yep, definitely in Canada!  A Canadian flag on the station in St. Catharines, Ontario.

The "VIA set-up" on the Amtrak Amfleet Cafe car between Niagara Falls and Toronto

My VIA coffee cup, napkin, and menu on the Amtrak Amfleet cafe car

The Maple Leaf passes and a Southern Ontario Railroad freight engine

Even though we knew we would be up to the wee hours of the morning with a very late Canadian departure ahead of us, we were happy that we made the connection between the Maple Leaf and the Canadian, as this was the tightest connection on the entire trip that we had scheduled.  There was just a little over two-hour window to make our trains in Toronto given normal circumstances. There has been times that the Maple Leaf has gotten into Toronto after the 10:00pm scheduled departure of the Canadian. I am not sure if VIA would actually hold the Canadian either for the Maple Leaf, but we certainly didn't want to find out either.  Pulling into the station in Toronto, we actually saw the Canadian being serviced out in the yards.

The Toronto skyline can be seen across Lake Ontario as the Maple Leaf approaches

Due to a baseball game, the commuter platforms at Toronto station were quite full on the evening of Saturday, September 8th, 2017

The Maple Leaf arrives into Toronto Union Station and the long wait begins for the delayed departure of the Canadian

Well, this seems like an excellent place to end the first section of this blog... two trains down and three trains and a ferry ride to go before arriving in Alaska. Check back in a few weeks and we'll throw up Part 2 of 4, which will cover our journey between Toronto and Jasper on VIA's Canadian.  In the meantime, maybe begin plotting your own trip between Chicago and Alaska using trains and a ferry.



Amtrak "Lake Shore Limited" |  Amtrak/VIA "Maple Leaf" |  VIA "The Canadian"VIA "The Skeena"Alaska State Ferry System

More information about VIA Park CarsJasper SkyTramColumbia Icefields ParkwaySitka National Historical Park


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