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Boston's biggest Annual Events:
Boston Calling (a bit surprised you've never heard of it as it's one of the 15-20 largest music festivals in the US now, but it takes a back seat to the more substantial and traditional music festivals like Lolla no doubt)
Boston Marathon (it's bigger than the Air and Water Show, believe it or not)
Feast of Saint Anthony (google image it)
Head of The Charles (as it's known, The Regatta, which you may be familiar with)
Boston Harborfest
And above all else, Boston Pops 4th of July
Saint Anthony’s Feast is my favorite event in Boston, but I don’t know if it has much recognition outside of the area. Honestly, that’s one of the things I like best about it.
Yeah I get that if you like cities you’d rather be in Edgewater or Lincoln Square than West Roxbury, but it’s not like someone who lives in River North or Wicker Park would have any reason to go to Edgewater.
I guess what I wanna know is if we just look at the inner ~30 sq miles or so — which I believe is where most people living in the urban core will spend the vast majority of their time — what does Chicago do (other than nightlife) appreciably better in terms of things that are relevant to day-to-day urban experience (eg cool neighborhoods, restaurants/bars, street vibrancy, interesting people, public transit and ease of getting around, urban character etc)? Or is it just that Chicago’s urbanity stretches much farther so there is simply more “stuff” over a larger area ... and that’s really it?
That’s sort of of what I was getting at earlier. I think you can say that Chicago does bars/nightlife appreciably better than Boston within that inner ~30 miles. Other than that, I’m not so sure.
I enjoy reading your posts and you seem like a knowledgeable and objective poster. I find it curious though that you talk up Chicago so much but at the same time say that you enjoyed living in Boston more. So what gives?
Whenever Chicago is compared to “lesser” cities, it is always “Chicago is bigger” etc etc. That’s also consistent with my real life experience with people who have lived in Chicago — they have a uniformly high opinion of the city, but when you try to dig in a little it always comes down to the same thing — “Chicago is bigger so there is more of everything.” Boston, OTOH, is “small, overrated and overpriced”.
I am sure there is something to it if everyone says it (and of course we do know that Chicago is much more affordable and has better nightlife — there is no question about that) but if we go a little more “micro” (in your words) and compare the areas of each city that a typical resident/young professional is actually likely to be exposed to day-to-day, is there really a big size disparity that supports this default assumption that “Chicago has more of everything”? No agenda, just an honest question. So if you compare, say:
Downtown Chicago + West Loop + Old Town/GC + LP + LV + WP + Bucktown + Logan Square
VS
Downtown Boston + North End + Beacon Hill + Back Bay + South End + Seaport District & South Boston + Fenway-Kenmore + Cambridge
[feel free to add any other happening areas I missed out]
Does Chicago clearly come out on top in that comparison? If so why and where? I am not particularly interested in once a year music festivals, but more in the day-to-day — street buzz, cool bars/restaurants/coffee shops, quality and accessibility of public transportation and the ease of getting around, etc.
Being that these are my two favorite cities, I think it'd be normal practice for anyone to talk up both on any given post/thread. And, "on paper", I like Chicago over Boston. Generally, as a city, I express just that in side-by-side comparisons.
To your point, I like living in Boston more. There are certain pockets in Boston that I think are favorable to their Chicago counterpart. While not taking into consideration size, I like Back Bay more than Gold Coast. I like the North End more than [enter Chicago equal here]. I like Cambridge/Somerville more than Wicker/Bucktown/Logan Square. I like Brookline. I like Seaport. I love the South End. I like Newbury Street more than Michigan Ave. But, I like Old Town more than Southie. I like downtown Chicago more than Downtown Boston. I like the West Loop more than [enter Boston equal here]. Boston doesn't even have a Lincoln Park equivalent. Chicago's waterfront is superior to Boston's waterfront.
Overall, they are both great. Chicago is bad*ss, large, practical, diverse, loud, energetic. Boston is beautiful, unique, impractical, prideful, progressive, safe, often more manageable. Key difference is the surrounding areas. In Boston, it's adventures every weekend to all of the Eastern MA bike paths, inlets, rivers, coastal towns like Marblehead, upscale outdoorsy enclaves like Concord. We love NH, VT, ME.. Mountains, wineries, breweries, cliffs, waterfalls. In Chicago, it's Naperville, Geneva, maybe Galena, or the city itself. Western Michigan is a weekend getaway, but despite the branding, doesn't deliver even 1/4 of what the East Coast does when considering beauty, food, culture, exploration. And that is the only part of this post that is not up for debate
Another tangible difference is, while Chicago no doubt offers far more high end dining, and a stronger local food culture.. Boston and it's surrounding suburbs are very much a healthy/coffee/doughnut/farm-to-table/beer area (which are somehow all intertwined in 2019). I know all of that exists in droves in Chicago, but it's a larger part of Boston's fabric- Not quite like Portland, OR or Portland, ME, but very prevalent all the same. I just feel like that is a microcosm of how Boston can feel more approachable/usable on a daily basis than Chicago (not the people, of course).
Saint Anthony’s Feast is my favorite event in Boston, but I don’t know if it has much recognition outside of the area. Honestly, that’s one of the things I like best about it.
Bostons Caribbean Carnival is probablly bigger than everything but the Boston Marathon Boston pops and First Night. Its enormous
I think "having more" because the city is 2x larger really is the only argument. If you shrank Chicago and Boston to the inner 20-25 sq miles they would be similar but after that Chicago has far more neighborhoods while Boston has places like Waltham and West Roxbury which are really only Semi-urban.
However I think people just give Chicago the Transit win when if you look at actual ridership the MBTA has a higher transit share in the metro area and there is actual connection between Commuter rail and subway access while in Chicago you have to walk a couple blocks from Union Station to the L.
... and Chicagoans also have to hoof it a couple blocks to the Metra Electric terminal at Millennium from the nearest L stations (from State/Lake on the Red Line subway and from Washington/Wabash on the joint-line Loop elevated). Both the Ogilvie and LaSalle Metra terminals are better served by L stops.
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