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Boston or Chicago?

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  • I love Boston but if shopping is important it has to be Chicago. That's one thing that lets Boston down, the shopping isn't great.

    If you're going for a week there's no reason why you can't do both!
  • bigadaj
    bigadaj Posts: 11,531 Forumite
    Ninth Anniversary 10,000 Posts Name Dropper
    Boston is great. Having said that, I remember really liking Chicago, but that was back in 1986 so the details are a bit blurred.

    If outings by train are important to you, then Boston is on the main line between Montreal and Washington, while Chicago probably gets one train a week (and while they go to interesting places they take days and days to get there).

    I still think you should take her to Cuba instead: all the aspects of Boston that are great are present even more vividly in Santiago.

    Trains between Montreal and Washington will generally go through Albany and New York, Boston would be a big diversion on that trip.

    I'd say Chicago is far more of a rail hub than Boston, though as you say these are mainly long distance.

    A week in and around Boston would probably be more interesting, lots of coast and history to explore within a reasonable distance.
  • ince_mon
    ince_mon Posts: 323 Forumite
    Archergirl wrote: »
    Which one would she prefer?

    I'm paying,nothing to do with her.:D:D
  • I loved Boston so much I have been twice and I am thinking about a third time to catch some of the things that I missed before, it is such an easy city to get around and although it is mostly history and baseball orientated I still found it very interesting with the university and medical connections and more importantly 'safe' to walk around as well.
    Within easy reach of NY and Washington DC even for just a day trip.
  • DigForVictory
    DigForVictory Posts: 12,054 Forumite
    Part of the Furniture 10,000 Posts Name Dropper Photogenic
    Boston - been there, loved it & Not on the Grid system, much more homelike. Some architecture which the locals revere as ancient & we regard as mildly familiar.
    Faneuil Hall for gastro treats, and also a mall. Bookshops galore & Symphony Hall then still in range of the coast & all the "darn, that's Big" of the sweep of water. Autumn colours just sensational <nostalgic sigh>.
    Also, short hop by train or Greyhound back to Washington for flights etc.

    Chicago also has loads of good points but my heart belongs to Boston.
  • I've not been to Chicago to offer a compare, but really liked Boston.
    Don't miss The Freedom Trail (all about how they rose up against the boo hiss, nasty Brits)
    Using the water taxi service was a cracking way to view the city as well.
  • dondo
    dondo Posts: 526 Forumite
    Part of the Furniture 100 Posts Combo Breaker
    I've been to Boston a goof few times over the years but Chicago only once. Overall I probably prefer Boston but that maybe due to the fact that when I went to Chicago that 1 time I had been travelling around the states for about 4 weeks by that stage and was probably I little weary.

    That said I do love Boston- like others have said there is a lot of history there and also Cambridge where Harvard University is. There is the freedom trail which takes you around all the significant historical landmarks etc., the JFK museum is really interesting, and it's a relatively compact city with a good underground system
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