First Time Doing Extensive Traveling

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In several months at the end of March of next year I will be traveling to Maine from Illinois via train. I can navigate Pontiac and union station in Chicago just as well because I’ve been there before. But beyond that I’m gonna be so freakin out because I’ve never travelled outside of Illinois on a train before so I really need help on what my options are. Any help is appreciated. Thanks in advance everyone
 

Maglev

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Hi Vicki!

There are a few different ways to get from Illinois to Maine by train. Are you interested in a scenic train trip in a luxury sleeping car with leisurely overnight stops, or would you be more interested in a journey with overnight travel in a chair car and a bus connection from Boston to Maine?
 

pennyk

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On what trains will you be traveling?
Do you have tickets yet?
Do you plan to get a sleeper?
 
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No sleeper, can’t afford it. And I’m gonna have overnight trains from Chicago to DC and then DC to Boston. It’s beyond Chicago that I’m freakin out about. I’ve never travelled this far by train before.
 
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Hi Vicki!

There are a few different ways to get from Illinois to Maine by train. Are you interested in a scenic train trip in a luxury sleeping car with leisurely overnight stops, or would you be more interested in a journey with overnight travel in a chair car and a bus connection from Boston to Maine?
I’m gonna be doing the last option you mentioned
 

crescent-zephyr

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I would recommend that you change your travel plans... you want to go from Chicago to Boston, single overnight, on the Lake Shore Limited. From Boston you can take an easy quick bus or train up to Maine.
 

crescent-zephyr

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How would I go about getting that route?
Just search for Chicago to Boston on amtrak.com. It's train #448 - the Lake Shore Limited.
It arrives at Boston South Station at 8:01 PM.

Concord Lines offers Bus Service from Boston South Station to Portland (and other areas of Maine) every hour. So you can catch the 9:15 PM bus and be in Portland about 11:00 PM.
 

MARC Rider

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It looks like there's only one way that Amtrak will sell you a through ticket:

Cardinal from Chicago-Washington
Northeast Regional 66 from Washington to Boston (leaves Washington at 9:40 PM, gets into Boston at 8 the next morning.)
Thruway Bus (probably a Concord Coach) from Boston South Station to Portland.

The Lakeshore Limited gets into Boston 8 :10 PM -- if it's on time. I'm not sure when the last Concord Coach leaves South Station for Portland. Anyway, Amtrak won't sell you a ticket using that routing. You could do it if you want to stay overnight in Boston.

If you take the Capitol, you'll get into DC shortly after lunchtime, but I don't think they'll book you on a regional that leaves before 3 PM. A Regional takes about 7-8 hours to Boston from Washington. That means if you leave at 3 you'll get to Boston at 11PM to midnight. I'm not sure if there's a Boston-bound Acela you can connect to from the Capitol; that might save an hour on the travel time, but I suspect you'd still get into Boston too late to connect to anything going to Portland.

There is Amtrak train service that runs between Boston and Portland called the Downeaster. However it leaves from North Station, not South Station, which serves all the other Amtrak trains. (There are two train terminals in Boston.) The last Downeaster of the day leaves North Station at 10:30 PM and arrivies in Portland at 12:55 AM. If you took the Lake Shore Limited to Boston, you would probably need to use a taxi or Uber to take you over to North Station (It's only a 5-10 minute ride) to make the connection.(You could take the subway, but it involves changing subway trains and is a real pain if you have luggage.) But, of course, there's no guarantee that the Lakeshore Limited will arrive on time.

Personally, if I were doing the trip and I were taking the Lakeshore Limited directly to Boston, I'd just stay overnight in Boston, and go to Portland the next day. If I were watching my budget, I'd take Amtrak's routing via the Cardinal, Northeast Regional 66, and the Thruway bus and arrive in Portland at noon, as opposed to sweating a non-guaranteed connection in Boston and arriving at 1 in the morning.
 

crescent-zephyr

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The last concord bus leaves south station at 11:15 pm. That allows for a 3 hour delay.

Let’s remember the OP is concerned about transferring at large stations. New York is arguably the worst. A one seat ride to Boston sounds the simplest to me!

I used to take the crescent to DC, switch to Acela to Boston, and then take the Downeaster to Portland. Amtrak said it couldn’t be done.... I proved them wrong! Ha.
 
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Just search for Chicago to Boston on amtrak.com. It's train #448 - the Lake Shore Limited.
It arrives at Boston South Station at 8:01 PM.

Concord Lines offers Bus Service from Boston South Station to Portland (and other areas of Maine) every hour. So you can catch the 9:15 PM bus and be in Portland about 11:00 PM.
I did some preliminary pricing on this and I’m gonna go with this. It still allows me to be able to book my return trip to Illinois within reason. And this option cuts my travel time nearly in half which I love
 

Rasputin

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I did some preliminary pricing on this and I’m gonna go with this. It still allows me to be able to book my return trip to Illinois within reason. And this option cuts my travel time nearly in half which I love
Going on the Lake Shore #448 would be the most direct option. You would board in Chicago and arrive in Boston with no change of trains and you would be in a through Chicago - Boston coach.

Be aware that you cannot check any luggage to Boston so you can only take carry-on luggage.

As a coach passenger the café car will provide the only meal service and you may want to check out the menu on the Amtrak website. I suggest you bring some of your own snacks. You can also rely on the store at Albany station to provide some sandwiches, snacks, salads, etc. and you can visit it during your stop at Albany. That store is a great place.

The other caution is that 448 is not a reliable train. It cannot be depended on to arrive in Boston on time and can at times be hours late. The last Concord bus to Maine (check out their schedule on line to be sure) leaves at 11:15 pm. If the Lake Shore is much more than 3 hours late, your options (unless you have good friends or relatives in Boston) are very unpleasant. One option is to obtain a hotel room in Boston for the night. Boston hotel rates are exceptionally high. The other option is that as an arriving Amtrak passenger you can spend the night on a bench in South Station. I have had to do that option twice when the Lake Shore arrived in Boston about 5 hours late each time and I don't recommend it. At least the station is closed to the public during the night and is staffed by security so it is safe. You can then catch the first Concord bus to Maine at 5:45 a.m.

As another caveat, for a first timer it is not obvious how you navigate from the South Station Amtrak station to the South Station bus station but it is not that bad and you should be able to do this. I would not recommend trying to go from South Station to North Station to catch the Downeaster train unless you like adventure. It just adds another complication.

Concord bus lines is an exceptionally well run company. In general they operate their service to please and serve their customers and the public has responded. Wish I could say the same for other transportation companies.

Hope you have a nice trip and let us know if you have other questions.
 

Rasputin

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Looking at the Amtrak delay data, it appears that twice in the past month (Sept, 4 and August 14) 448 would have arrived in Boston too late for passengers to connect to the last Concord bus to Maine departing at 11:15 p.m. That is reasonably good performance for 448 but it can be sometimes much worse.
 

Lonestar648

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I have traveled from Chicago to Portland or Bangor many times. Each time I was on 448 going to Boston so I didn't have to change trains. In Boston, I have taken the bus which was very easy (security people were very helpful in pointing the right direction), the Downeastner, which I took a cab just to be on the safe side, and I have rented a car which required a taxi due to the lateness of arrival. Don't worry about the stations, Chicago or Boston, both are easy to navigate, plus there are people Amtrak and Security to ask for directions.
 
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