Chicago or Boston?
 

Hi,

I will be visiting the states next month and have a 3-night part of the trip which is still to be decided... We're a couple and looking to visit either Boston or Chicago.

We like trying out different types of food, spending time at cafes, art, historical sites (just me but we'll make do :p), and sightseeing! We're not really into sports or outdoor activities.

Any ideas to which might be better? If dates are any decider, we are looking at 11-14 Oct.

Thanks in advance!

Boston should be very busy next month hosting leaf peepers there and on their way further north to see the colors. Rooms may be at a premium.
The city is very much about history: Revolutionary War sites on the Freedom Trail and in the suburbs, a Black Heritage Trail, a now-gentrifying Italian neighborhood that has seen changes in the ethnicity of its immigrants over the centuries, traditional brownstone architecture on picturesque Beacon Hill, witch trial history in Salem, traditional seaports nearby, etc. There are many "ethnic" restaurants dotted around the neighborhoods. Lobster is featured on many menus. The city is very much connected to its harbor and the ocean, although by next month it may be a bit cold for many activities. The MFA has some good collections and the Gardner Museum is unique. The PEM in Salem can be reached by train. There is an Aquarium known for its three story central tank, and a science museum. There are pleasant cafés everywhere, including the Italian North End, Harvard Square in Cambridge, Davis Square in Somerville, and wherever there are students (which, because of the number of educational institutions, covers the whole area). It is a pleasant city for walking.

I have to say though that I once drove six hours in the snow with some friends from rural Ohio, and back immediately afterward, simply to spend six hours at the art museum in Chicago--and considered it well worthwhile.

Chicago X1000. And if the weather is nice (which I hope because I'll be there around the same time), take the architectural boat tour. Chicago is hands down the most beautiful city in America, it's way easier to get around than Boston, and you can spend an entire free day (or 4) just walking the city and the cool neighborhoods and looking at the architecture. The Chicago Marathon is on the 12th, so hotel rooms in the city will be hard to get until Monday night, but just stay a little outside - the public transport is easy. Plus you can watch the runners.

Chicago, Chicago, Chicago!

What has been your experience to base such a statement on? Please expand on this.

Boston

Lobster, lobster bisque, clam chowder, the North End Italian cuisine from vitello to cannoli, The Museum of Fine Arts, The Isabella Stewart Gardner Museum, lighthouses, boat rides, it's a walking city with a good public transportation, the Charles, the Freedom Trail, Faneuil Hall, Cambridge, daytrips via commuter rail to coastal historic towns like Gloucester and Rockport, gorgeous foliage (lots of red maples), etc.

Because Boston is ideal in mid October, you might be too late to secure hotel accommodations so you might end up choosing Chicago by default.

As a Chicagoan, I'm a huge fan of our city, but if you have little interest in the Marathon, you might want to consider Boston on those dates. One of the great things about the Chicago Marathon is that it takes runners through so many neighborhoods. It's also easy for spectators to cheer on family & friends from several points on the route getting around via public transportation. But...major parts of the city are largely inaccessible for a good portion of the day, and this includes a lot of the major tourist areas. If you only have three days to sightsee, you'll have to make some serious compromises on Sunday -- particularly in the morning -- unless you carefully plan your itinerary for the day to avoid/circumnavigate points on the marathon route. (It's not an exaggeration to say that it could take you 45+ minutes to cross the street at some points on the route, particularly those spots in the first ~8 miles when runners are tightly bunched together.)

If you were staying outside of downtown, you'd be able to spend the morning at the Museum of Science and Industry. Or the outlet mall, which is a perpetual favorite of many visitors from other countries.

Also, everything's relative when it comes to "historical sites" in Boston vs. Chicago. Chicago was founded in 1833, Boston was founded in 1630. Boston is chock full of sites that are central to American history. Not so in Chicago. So while we have historic sites, they're usually of interest to a narrower group of people. If you're not a native of the US, I can't imagine more than a couple historic events that occurred in Chicago which you'd be aware of. The Chicago Fire? (Not much to see.) The 1968 Democratic Convention? (It's a hotel.)

I've already booked refundable hotel stays at both cities so accommodation is not an issue...

Looks like there is no clear consensus on which might be the better city to visit (my searches on the web indicate similarly too...). Currently slanting towards Boston, since the stop after that will be NYC and Boston is close.

Analise - why is Boston ideal in mid October?

That's terrific.

The crisp weather as it is a great walking city especially for the Freedom Trail, the foliage both in the city itself (Boston Commons & the Boston Public Garden) and in the towns I suggested by commuter train in mid October will be especially beautiful, the museums I mentioned, the restaurants, the neighborhoods, the BSO, etc.

From a weather/foliage perspective, Boston and Chicago both have very similar climates. Don't let that sway you one way or another.

If your next stop is NYC, Boston is about an hour closer via plane than Chicago.

If you need more help making the decision, why don't you share a list of the attractions you'd most like to visit in each city?

I'd just like to point out that Chicago is an actual city, while Boston is essentially a large town with pretensions. Here's the Onion's commentary... :D

<ducks and hides>

That said, if you're specifically interested in American history, Boston is the no-brainer choice. But in terms of everything else, Chicago has Boston beat cold.

Museums? Chicago wins with the Art Institute, Museum of Science & Industry, Museum of Contemporary Art, and a few others.

Food? Chicago has everything in quantity and quality. Every ethnicity and style, from down home to three star Michelin restaurants.

I'd also highly recommend an architectural boat cruise.

In terms of public transport, I think you'll be fine in either city.

If you plan on going to NYC before or after, I wouldn't worry too much about it. There are multiple flights per hour between NYC and Chicago, and between Boston and NYC. Boston has the advantage of train connections too.

Which hotels have you booked in each city? This would determine if your visits would truly be walkable. There are plenty of hotels that would be great to start walking tours from. Both cities are among country's finest. Boston for history, Chicago for architecture. Both for people and dining.

Yah bettah hayd !!
But really, that's one of the beauties of Boston, a 'town' feeling with all the advantages of a city.

No offense to the city of Chicago, but both of these statements are patently absurd.

I grew up in Boston and now live in Chicago. Love both cities and each have their unique characteristics. Boston is a fraction of the size of Chicago. The upside to this is Boston is very walk-able. If you go there don't rent a car because driving around the city can be an adventure and parking expensive. For history and good seafood, Boston can't be beat. Fall is one of the best times there for the weather and atmosphere.

I pretty much second everything said here. Boston's beautiful, but it's kind of boring :D