Chicago Vs Boston

R

Ron Burgundy

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Hi all,

Thinking of heading away in Nov with Mrs Burgundy.

We are looking at 4 nights in either Chicago or Boston.

So whats to do in each and have you been and whats your thoughts ?
 
I've been to both, Boston once in 2001, and Chicago twice 2004 and 2009 the 2009 trip was work. I found chicago to be great for shopping, theatre and museums but didn't do much else.
Boston was great far bars, museums, shopping and all round interesting things to do and see.
I enjoyed both but would put Boston ahead as I felt there was more choice in things to do and they seemed more interesting.
That's just my take on it though.
 
I have been in Boston but not Chicago. Boston is a good spot for that length of time. There are a lot of museums (JFK, museum of fine art, contemporary museum) good bars, restaurants and general atmosphere. Some good shops too for Mrs Burgundy!! Ducks tour is nice to do - it's by road and water. Climbing the Prudential Tower gives great views over the city. Can't compare it to Chicago for you though.
 
Chicago for me all the way been to boston a few times and Chicago. Chicago has much more of a buzz to it then Boston IMHO.
 
i lived in Boston for 8 years and although obviously biased,there is alot to do in boston on a short trip. they have all the usual tourist things to do like the famous duck tours, the jfk museum and cheers. there is great shopping on newbury street, downtown (filenes basement) and some great shopping centers like the prudential center. Boston is a small city and very easy to get around. and obviously there is a great irish connection and loads of good irish bars and plenty top class restraunts.
 
I have been to both and would go for Boston for the same reasons that others here have stated .also you could nip down to New York for a night too from Boston
 
I visited both Boston (1 week) & Chicago (2 weeks) about 4 years ago. Chicago, in my opinion, is by far the better city to visit - it is clean, has great parks by Lake Michigan, great jazz & blues music, the people are approachable & friendly & there are loads more places to see & visit in Chicago. Granted the "big dig" was still going on at that time in Boston, so this may have influenced my opinion.
 
YOBR said:
I have been to both and would go for Boston for the same reasons that others here have stated .also you could nip down to New York for a night too from Boston
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How long does it take to get from Boston to New York, it might be a nice suprise for my wife.
 
It takes about 4.5 hours on the bus, we did it with the Peter Pan busline.
The climate in Boston could be a bit more forgiving that Chicago in early November, Boston (and the whole of New England) is stunning in the fall/autumn.
Pity the baseball season is over as a trip to Fenway is a must.
If you're into that sort of thing you could try and get a New England Patriots game but the stadium is about 20 miles outside the city.
 
NorfBank said:
It takes about 4.5 hours on the bus, we did it with the Peter Pan busline.
The climate in Boston could be a bit more forgiving that Chicago in early November, Boston (and the whole of New England) is stunning in the fall/autumn.
Pity the baseball season is over as a trip to Fenway is a must.
If you're into that sort of thing you could try and get a New England Patriots game but the stadium is about 20 miles outside the city.
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No i'm a Colts fan and they are playing the Pats that weekend:D

A 9 hr round trip to NY would be too much on a 4 day trip to be honest.
 
Ron Burgundy said:
How long does it take to get from Boston to New York, it might be a nice suprise for my wife.
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I did this while on a holiday in Boston. Go online and get a cheap commuter ticket - they tend to be cheap on weekends as they are used mainly by business people. Planes go to La Guardia Marine terminal which is about the size of Busaras - so the experience is more like taking the bus than an airport. Flight time is c. 1 hour. You can easily spend 12-15 hours in NY, which is enough time to get to a couple of the major sites and have lunch in downtown Manhatten.

Been to both Chicago and Boston and I like both cities. Boston is more tourist orientated, so probably better for a short break.
 
kevinbarry said:
i lived in Boston for 8 years and although obviously biased,there is alot to do in boston on a short trip. they have all the usual tourist things to do like the famous duck tours, the jfk museum and cheers. there is great shopping on newbury street, downtown (filenes basement) and some great shopping centers like the prudential center. Boston is a small city and very easy to get around. and obviously there is a great irish connection and loads of good irish bars and plenty top class restraunts.
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I have never really been impressed with Filenes basement it is just TK maxx lots of rubbish and you have really have to dig to find anything decent.
 
You could also take the train i think that is about 2 hours and the trains are lovely we did once when in boston.
One other thing to think about is the lenght of time that you are going for Boston is a shorter flight than Chicago
 
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