Today's matchup is the showdown of the places I lived for five years each while going to school: Chicago vs Boston! Two metro areas I have a lot of love for, both of which I lived in and have repeatedly visited without a car (and a few times with one). It's a shame we can only have one winner, but at least the victor will have vanquished a worthy foe.
Category 1: Visiting Without A Car
a) How can you get to the city?
Boston technically has airport public transit, though the janky Blue line bus-to-train connection is one of my least favorite versions of this (and the Silver Line can't decide how RT its BRT wants to actually be).
Chicago has its own Blue Line to O'Hare, though O'Hare is also very far out, and the Orange Line to Midway. Both of these are cities you can easily fly into and not need a car to do stuff.
Both also have good-for-the-US train service, with the Acela corridor ending in Boston (as well as other services) and Chicago serving as the Midwest hub for basically all Amtrak routes.
That said, Acela beats the pants off of the Chicago services for actually visiting the city, and Logan is nice and close to the city center.
VERDICT: Chicago 0, Boston 1
b) How do you get around?
The MBTA has reasonably good service around the Greater Boston Area, between buses and trains, and the downtown core of Boston is highly walkable.
The CTA and Metra also do a good job of covering Chicago from a visitor's perspective, though the Museum Campuses can be a bit of a slog from the nearest transit stops.
The biggest issue for both cities is that almost all transfers are done through downtown, even when an orbital line would go through very dense areas with tourist attractions.
Boston is just a bit more walkable between its major sites than Chicago, though, and a more compact area for visitors overall.
VERDICT: Chicago 0, Boston 2
c) What are the limits on a visitor without a car?
Well, in Chicago the biggest issue is ticket interchangeability: the Metra and CTA don't recognize each other.
In Boston, it's the sights that aren't on the MBTA at all: places like Lexington and Concord that are often lumped in with Boston area attractions but actually aren't very accessible.
Oh, and if you want to see the NFL team, good luck with that from Boston. Foxboro is a pain in the butt to get to, even with dedicated gameday service.
Frankly both cities are pretty darn unlimited as far as visiting goes, but I'd give a small nod to Chicago here: there's never been a place I couldn't get to as a visitor without a car.
VERDICT: Chicago 1, Boston 2
Category 2: Living Without A Car
a) Can you expect to get to work?
Both of these cities have good commuter networks as long as you live outside the city center and work in it. Both struggle when you have to counter commute (commuting Boston to Newton for several months was rough).
Both cities also have high commuter/non-car mode shares. Both are awful places to drive to work, but allow you to avoid it--one of my friends commutes down the Lakeshore path in Chicago, for instance.
I really think this comes down to exactly where you choose or can afford to live and where you work.
VERDICT: Chicago 2, Boston 3
b) Can you live the rest of your life?
Yes, certainly! However, Boston to me has the edge on transit-accessible things beyond your work: I agree with this analysis that Boston might just be the best city in the US for that (though of course our competition goes beyond the US). The reason for this is that I tend to see, in my experience at least, more grocery stores, department stores, and other non-food amenities around T stops and major bus lines than the same in Chicago.
VERDICT: Chicago 2, Boston 4
c) How are the basic amenities?
This is another of those places where I'm going to call a tie: Chicago and Boston both have some issues with aging infrastructure and missing sidewalks, but they both have world-class museums and parks, fine access to public bathrooms, trash cans, etc...I never though to complain about these in either city.
VERDICT: Chicago 3, Boston 5
Category 3: Miscellaneous
a) Are there people on the street?
Yes, emphatically, in both cases, but here I think the multinodal character of Boston makes a difference: Chicago has more areas that are like the stereotypical American blocks of endless residential that tends minimize people's visibility on the street, while Boston is an agglomeration of smaller cities that tends to produce odd streetscapes that produce opportunities for street interaction.
VERDICT: Chicago 3, Boston 6
b) Where is the city's urbanism going?
Well, neither city is in good shape here: Chicago may be going over a transit fiscal cliff, and the MBTA isn't in great shape either. The T has a bad history as well. Both systems expanded to underserved communities in the last couple decades. But Chicago did it more recently, and the potential for Illinois to support real regional rail in the larger state, connecting to Chicago of course, tilts the balance for me.
VERDICT: Chicago 4, Boston 6
c) Is it functionally diverse?
Eesh. Like so many cities, this is a battle of the bad in terms of historical and ongoing segregation (with the admitted point that this means there is diversity in the community). Chicago has a long history here interrelated with the history of the Great Migration; Boston has a serious reputation for racism and the aftereffects of redlining. And lest we think these are in the past, both cities have school segregation issues in the present day. At the same time, both cities have racial diversity, even if that comes with the legacy of segregation; Chicago, however, is substantially less white than Boston. Since Boston hasn't done a significantly better job of integrating that non-white population, that tips the matter.
VERDICT: Chicago 5, Boston 6
d) How do people there react to knowing you're not using a car?
Both of these are cities where, in my experience, people tend to have no notable confusion or disdain for the lack of a car. However, Boston is much more likely to expect you not to have a car, whereas in Chicago it's much less of a surprise. Boston and Cambridge are 5-6 on this list of least-car-owning cities, and while Chicago is 15, which is still impressive, that's the tipping point between averaging over and under 1 car per household.
VERDICT: Chicago 5, Boston 7
e) How do people react to people living close together?
Again, it's a bit unfair for Chicago to be up against Boston here, because while Chicago and some of its suburbs are notably dense, and Chicagoans tend to be absolutely fine with density, Boston just outperforms it by a smidge. Glancing at the list of densest US cities confirms this: Chicago loves density, and Boston loves it just a bit more.
To be clear: no one* here is complaining that density is somehow inhumane or un-American.
*"no one" promise implies only a general sense of acceptance, not the actual absence of any cranks
But one of the cities is just a little more urban than the other.
FINAL VERDICT: Chicago 5, Boston 8
It feels appropriate the final score is the same here as in the Toronto-Vancouver matchup, as I feel very similarly about the dynamics of these city matchups: both are powerhouses unlucky to face the other in the first round, and yet in both pairs there is one city that is just a bit more in line with these criteria than the other.
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