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Boston or Chicago - which would you choose?

Boston or Chicago - which would you choose?

Old Nov 26th 2010, 10:40 pm
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Default Boston or Chicago - which would you choose?

Hi All,

A couple of weeks ago, I posted that my partner and I (to be husband in about 3 weeks!!) would be moving to Boston in the spring (on an L1/L2 visa) and everyone gave lots of helpful advice on good neighbourhoods. Today - his boss casually dropped into the conversation that they might send us to Chicago instead!

The plan is that we would only be based there for around 4-6 months and then move to Seattle - but to a certain extent we will be at the whim of the economy - the company will keep us where the customers are! So I want to make sure we would be happy if we had to stay there for a year or two.

We have the opportunity to state our preference. At the moment I'm leaning towards Boston, it seems like Chicago winters are harsher and the idea of being on the East coast and closer to other major cities really appeals to me. However, I'd be interested to hear what other people would do if given the choice. We're in our early 30s with no kids and used to living in a reasonably central part of London.

Thanks in advance for the advice!
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Old Nov 26th 2010, 10:50 pm
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Default Re: Boston or Chicago - which would you choose?

did you ever see that South Park episode where they were asked to pick between a Turd Sandwich and a Giant Douche?
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Old Nov 27th 2010, 5:40 pm
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by fashionista View Post

We have the opportunity to state our preference. At the moment I'm leaning towards Boston, it seems like Chicago winters are harsher and the idea of being on the East coast and closer to other major cities really appeals to me. However, I'd be interested to hear what other people would do if given the choice. We're in our early 30s with no kids and used to living in a reasonably central part of London.

Thanks in advance for the advice!
For just one winter, it wouldn't make any difference, it'll seem horrid to what you're used to in London....Boston winters are a piece of piss compared to the amount of snow they get in Chicago though, but how much fun it'll be depends on where you end up living and the parking situation. Boston winters really are a breeze though compared to western Mass or anything they get up in Maine and the roads get taken care of pretty well, bit shit with pavements in some times, but down town isn't a problem.

If you've got the cash to live down town and don't mind living in a pokey closet, you'd have everything on your doorstep in Boston and it'd be great fun without kids.

Flights from Logan to London are regular and relatively speaking, cheaper than a lot of other destinations and it's a good hub to get around, even if you will want to stab your eyes out trying to park at Logan. If you're going to be flying lots and likely not living or able to get public transport to the airport, figure out how much the parking might be in Chicago because it'll be cheaper spending a couple hundred to have a limo pick up/drop off than park at Logan for a week kind of thing.
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Old Nov 29th 2010, 12:19 am
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Default Re: Boston or Chicago - which would you choose?

I grew up in Boston, I've lived in Chicago for 10 years. My gross generalizations:

1. Boston is much smaller. Chicago's about five times the size population wise and many times the size geographically. Boston is very dense downtown, Chicago is much more spread out.

2. Boston is much "harder to live in" - more expensive, driving anywhere's a pain, the housing stock is relatively poor, the job market is very boom/bust (not a problem for you).

3. Boston is slightly more cosmopolitan. Chicago is an extremely "American" place in every way, Boston is slightly more outward looking. This may mean that Boston is slightly easier to adapt to than Chicago, I don't know. Of course, there are people from all over the world in Chicago so this is yet another gross generalization.

4. It's easier to get to New York from Boston. New York's a bit nicer than, say, Milwaukee. Vermont is gorgeous (although Wisconsin ain't bad). Western Mass is much more interesting than downstate Illinois.

5. The winters are a wash. Boston is much more "grey" and dismal. Chicago has more sun, but is unrelentingly arctic and snowy. I actually prefer winter in Chicago because it doesn't do the freeze/thaw cycle thing as much. But, you need to get out of Chicago in the winter for a couple of weeks, it's unbelievably cold some times...

6. Chicago is a true "world class" city. Boston has an "old money" feel to it, but downtown Chicago basically shouts power. Also, in general, Chicago has more going on than Boston. No major band, art exhibition, travelling play etc skips Chicago on a tour of the US. The Art Institute easily trumps the MFA. The Shedd kicks the New England Aquarium's ass. There are huge, wonderful festivals in Chicago every week year round, not so much the case in Boston.

7. Boston has wonderful little "niches", interesting and unique suburbs, strange obscure corners of the city, surprising and compelling little neighborhoods. Chicago also has disparate neighborhoods but is in general much newer and more homogenized.

8. People in Chicago are generally nicer and more modest than people in Boston. Huge generalization. People in Boston generally rate much higher on the pretentiousness scale. IMO.

9. It's really easy and cheap to fly anywhere in the US from Chicago. Boston not so much. If you want to see the country, Chicago's probably a better home base.

10. Fenway's better than Wrigley. It just is.

Last edited by Hiro11; Nov 29th 2010 at 12:22 am.
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Old Dec 1st 2010, 9:46 pm
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Hiro11 View Post
3. Boston is slightly more cosmopolitan. Chicago is an extremely "American" place in every way, Boston is slightly more outward looking. This may mean that Boston is slightly easier to adapt to than Chicago, I don't know. Of course, there are people from all over the world in Chicago so this is yet another gross generalization.
In my experience, Boston is far more provincial. Outward looking? This is the city where half the intersections don't have street signs, because if you belonged in that neighborhood you'd have known the street name since elementary school. You'd also know what the name changes to five blocks in either direction, where there also aren't street signs.

Bostonians are far more likely to have a snooty, insular, clannish focus on their city than Chicagoans.

You're right that Chicago is a world class city. Boston is tiny in comparison, and there is less going on. It's also more of a hassle and more expensive.

I'm not sure why you say Chicago is homogenized, its neighborhood variety is off the charts unless you restrict your travels to the yuppified areas of the north side. Yes, the northside neighborhoods full of Chads and Trixies with deluxe strollers and Cubs hats are all vaguely similar. The variety from Ukranian Village, to Devon, to Chinatown, to Berwyn, to Bridgeport, to Pilsen, etc, is huge. I'd say neighborhood variety is a calling card of Chicago.

Not trying to start a fight! I've lived both places, and like them both.

Last edited by Johnny Blood; Dec 1st 2010 at 10:03 pm.
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Old Dec 1st 2010, 11:31 pm
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Johnny Blood View Post
In my experience, Boston is far more provincial. Outward looking? This is the city where half the intersections don't have street signs, because if you belonged in that neighborhood you'd have known the street name since elementary school. You'd also know what the name changes to five blocks in either direction, where there also aren't street signs.

Bostonians are far more likely to have a snooty, insular, clannish focus on their city than Chicagoans.

You're right that Chicago is a world class city. Boston is tiny in comparison, and there is less going on. It's also more of a hassle and more expensive.

I'm not sure why you say Chicago is homogenized, its neighborhood variety is off the charts unless you restrict your travels to the yuppified areas of the north side. Yes, the northside neighborhoods full of Chads and Trixies with deluxe strollers and Cubs hats are all vaguely similar. The variety from Ukranian Village, to Devon, to Chinatown, to Berwyn, to Bridgeport, to Pilsen, etc, is huge. I'd say neighborhood variety is a calling card of Chicago.

Not trying to start a fight! I've lived both places, and like them both.
Yeah - Chicago's a bit shit. I prefer Boston.
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Old Dec 2nd 2010, 1:12 am
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Default Re: Boston or Chicago - which would you choose?

I would choose Boston, although I think Chicago is the third best city in the US (after San Francisco - of course - and New York City). The issue I would have with living in Chicago is that there really isn't that much to do outside of it, whereas Boston is pretty much surrounded by interesting places to visit that aren't a million miles away.
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Old Dec 2nd 2010, 1:51 am
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Giantaxe View Post
I would choose Boston, although I think Chicago is the third best city in the US (after San Francisco - of course - and New York City). The issue I would have with living in Chicago is that there really isn't that much to do outside of it, whereas Boston is pretty much surrounded by interesting places to visit that aren't a million miles away.
Yes - New England's brill. I love all the boaty stuff you can do from Boston in the summer - Provincetown, Salem, Harbor Islands and whale watching etc. Nearby you also have Nantucket, Martha's Vineyard and Block Island. I just love buggering about on boats in the summer!
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Old Dec 2nd 2010, 2:40 am
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Giantaxe View Post
I would choose Boston, although I think Chicago is the third best city in the US (after San Francisco - of course - and New York City). The issue I would have with living in Chicago is that there really isn't that much to do outside of it, whereas Boston is pretty much surrounded by interesting places to visit that aren't a million miles away.
Yes - you're right there. I lived in Chicago (in the suburbs). It is a great city and there is a lot to do there, but that's it - Illinois is a very boring state and it is far from everywhere. I've never been to Boston though - it's on my "bucket list".
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Old Dec 2nd 2010, 5:01 pm
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Hiro11 View Post
It's really easy and cheap to fly anywhere in the US from Chicago. Boston not so much. If you want to see the country, Chicago's probably a better home base.
Yes - while connecting through ORD is a real pain with a very high probability of missing your connection or getting stuck at the airport because of flight cancellations having it as the end point on your itinerary isn't nearly as bad.
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Old Dec 2nd 2010, 8:00 pm
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Hiro11 View Post
I grew up in Boston, I've lived in Chicago for 10 years. My gross generalizations:

1. Boston is much smaller. Chicago's about five times the size population wise and many times the size geographically. Boston is very dense downtown, Chicago is much more spread out.

2. Boston is much "harder to live in" - more expensive, driving anywhere's a pain, the housing stock is relatively poor, the job market is very boom/bust (not a problem for you).

3. Boston is slightly more cosmopolitan. Chicago is an extremely "American" place in every way, Boston is slightly more outward looking. This may mean that Boston is slightly easier to adapt to than Chicago, I don't know. Of course, there are people from all over the world in Chicago so this is yet another gross generalization.

4. It's easier to get to New York from Boston. New York's a bit nicer than, say, Milwaukee. Vermont is gorgeous (although Wisconsin ain't bad). Western Mass is much more interesting than downstate Illinois.

5. The winters are a wash. Boston is much more "grey" and dismal. Chicago has more sun, but is unrelentingly arctic and snowy. I actually prefer winter in Chicago because it doesn't do the freeze/thaw cycle thing as much. But, you need to get out of Chicago in the winter for a couple of weeks, it's unbelievably cold some times...

6. Chicago is a true "world class" city. Boston has an "old money" feel to it, but downtown Chicago basically shouts power. Also, in general, Chicago has more going on than Boston. No major band, art exhibition, travelling play etc skips Chicago on a tour of the US. The Art Institute easily trumps the MFA. The Shedd kicks the New England Aquarium's ass. There are huge, wonderful festivals in Chicago every week year round, not so much the case in Boston.

7. Boston has wonderful little "niches", interesting and unique suburbs, strange obscure corners of the city, surprising and compelling little neighborhoods. Chicago also has disparate neighborhoods but is in general much newer and more homogenized.

8. People in Chicago are generally nicer and more modest than people in Boston. Huge generalization. People in Boston generally rate much higher on the pretentiousness scale. IMO.

9. It's really easy and cheap to fly anywhere in the US from Chicago. Boston not so much. If you want to see the country, Chicago's probably a better home base.

10. Fenway's better than Wrigley. It just is.
Back in 1998, elder daughter had to chose between living in Cambridge MA or Evanston IL for school -- in the spring visits she loved both places. As a LA girl, she felt that the Boston winter would be easier to deal with.

When you mention Fenway and Wrigley it makes me realize that Dodger Stadium is now the third oldest stadium in the Bigs and I remember when it was built. Sigh. The Big A is not far behind. I remember attending an Angels game in their inaugural season at Wrigley Field in Los Angeles. I also attended games in the old Yankee Stadium. The less said about Candlestick Park, the better.
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Old Dec 5th 2010, 12:40 am
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Default Re: Boston or Chicago - which would you choose?

Wow! Thanks so much for all the comments. It sounds like we'd be able to find something to make us happy in both places - which is reassuring! I'd assumed that Boston would have more to offer than Chicago in terms of theatre and concerts, so it's interesting to hear that's not the case. Although I do think it sounds like Boston might be easier to adapt to in the short term.

As I type this I'm in mid-air flying from New York to Seattle and starting to get very excited about the move next year!
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Old Dec 5th 2010, 1:01 am
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by fashionista View Post
Wow! Thanks so much for all the comments. It sounds like we'd be able to find something to make us happy in both places - which is reassuring! I'd assumed that Boston would have more to offer than Chicago in terms of theatre and concerts, so it's interesting to hear that's not the case. Although I do think it sounds like Boston might be easier to adapt to in the short term.
Depends what you're looking for, there are boat loads of theatre all over the place, just not the big massive broadway shows, but there are loads of places that put on great productions all over, dare I say it, because Worcester is a shit hole, but the DCU centre does have a lot of great shows and the TD Garden in beantown has a lot going for it too and they get loads of concerts.
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Old Dec 5th 2010, 4:48 am
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Hiro11 View Post
Fenway's better than Wrigley. It just is.
No, it just isn't
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Old Dec 5th 2010, 3:05 pm
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Default Re: Boston or Chicago - which would you choose?

Originally Posted by Maishe View Post
No, it just isn't
Fenway is pretty awesome...parking is pretty shit but that's the same for most of downtown.
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