Boston or Chicago for the gay guy on the go?

July 28, 2009 5:36 PM

Boston or Chicago -- which is the better city for the gay traveler?

I'm starting to think about a little getaway weekend in the fall, and some quick snooping suggests that Boston or Chicago might be decent options. They're both appealing, but I don't know a lot about either one.

Which city would be more worth my while? I'm gay, mid-thirties, I like going to gay bars (more pubby, less dancey, generally) but I also like museums, galleries, hanging out in cafes, and good food. I'm really thinking about a whirlwind trip -- fly in Friday evening, fly out Monday... but could certainly tack on an extra day or two. I'm currently in Toronto.

Please, hope me decide!

posted by sevenyearlurk to travel & transportation (18 comments total)

Provincetown is gorgeous and has the pubs, museums, good food/cafes, and a million galleries. If you're not up for the drive from Boston, there's a sea ferry that goes from Boston to PTown.
posted by jerseygirl at 5:51 PM on July 28

Chicago has so many cultural options, things are fairly close together and easy to get to via public transportation, Autumn is a beautiful season here, and there are tons of gay bars, and decidedly queer-friendly restaurants, cafes and shops. The Boystown neighborhood along North Halsted street might be an obvious nightlife destination (although some-- not all--the bars there are kinda dancey) but there also are several other interesting parts of town, e.g. Andersonville and Uptown, that attract a more eclectic, laid back, older crowd.
posted by applemeat at 6:10 PM on July 28

Provincetown is great in the summer, but if you want to make your trip later than September, it'll be pretty deserted and kind of cold and bleak.

Boston's South End is kind of a gay mecca and just a generally beautiful neighborhood. I'm too poor to spend time there, but I hear it has great bars, cafes, and restaurants. I'm sure you could find a charming brownstone B&B. And, of course, Boston has plenty of great museums that you could find with a quick Google search.
posted by oinopaponton at 6:12 PM on July 28

If you go to Chicago, besides the Field Museum, Millennium Park, the newly expanded Art Institute, the Museum of Contemporary Art, and the (free) Lincoln Park Zoo - you might also hit something like Pilsen's 2nd Fridays Open studio/gallery night. I'm sure Boston ha similar things. Just a thought.
posted by unmake at 6:57 PM on July 28

I feel that North Halsted is a bit dance-party as well.
But the name Boystown wasn't given for no reason, and I got to find that out walking down that street alone at night. Needless to say I felt quite out of place, as you know, not fitting the criteria.
It gets less crazy if you go farther away toward Broadway & Belmont. And I'm assuming the party drifts over onto Clark too, and it's still funny to me that the whole thing is directly next to the baseball/sports/burly type crowds.
And I've found that Andersonville is for old women...and Uptown is just scary.
Sorry if that was no help at all.
posted by lhude sing cuccu at 7:03 PM on July 28

Chicago's Boy's Town is a de facto gay district with a broad appeal.
posted by wfrgms at 7:05 PM on July 28

Uptown isn't so scary.
posted by applemeat at 7:24 PM on July 28

(Whoops, sorry about that above) Uptown isn't so scary.
posted by applemeat at 7:27 PM on July 28

Halsted St. in Boystown Chicago isn't as "dancey" as it used to be. In fact as far as I know the only dance floors now are at Spin, Roscoe's and Circuit. (I haven't actually been in Hydrate yet, it might have one.) And Roscoe's is very pubby in the front, just with some dancing in the back.

But that still leaves many many bars of various types. Including Sidetrack, Minibar, Buck's, North End. (And Scarlet if they get it rebuilt...) Personally I dig Sidetrack - and if you're here on a Sunday evening and you're gay you really owe yourself a visit to Sidetrack's famous "showtunes Sunday." It runs from about 4pm - 9pm, but is most fun (and crowded) from 6pm - 9pm. Try a slushy, and stick in or near the front bar where all the crowd jokes happen.
posted by dnash at 8:48 PM on July 28

"... Boston's South End is kind of a gay mecca and just a generally beautiful neighborhood. ..."
posted by oinopaponton at 9:12 PM on July 28

As a former resident of the Boston area, I'm simply going to suggest that, if you take cabs around Boston, looking for gay bars, that you be sure not to confuse the South End with Southie, or South Boston. One is most definitely not the other, and Boston is a much smaller geographical area, to the mildly inebriated, than it sometimes should be.
posted by paulsc at 9:51 PM on July 28

EVERYONE can get married in Boston; it's more walkable and has more literary sites. Chicago is better for foodies and because it's the bigger city, there's more stuff going on. Both places have excellent museums.

Having spent significant time in both places,my preference is for Boston.
posted by brujita at 10:33 PM on July 28

I had a nice time at a gay bar in Chicago. I so rarely have nice times in gay bars that this was pretty remarkable. I did not have a nice time at a gay bar in Boston. This is not noteworthy.

I also happen to really like Chicago, and really dislike Boston, outside of the merely gayish parts of the towns, but YMMV. I suspect you'd have a fine time either way. Chicago is more Torontoish, in some ways.
posted by Casuistry at 11:19 PM on July 28

I just got back from a great trip to Chicago, and I grew up in the Boston area so this one has me torn.

If you are planning a fall trip, the P-town ferry will probably not be running, so don't let that influence you.

Boston - great museums, wonderful historical sights, a very compact urban core so you could easily (and quickly) get everywhere you want to go. In the fall, Boston/Cambridge is filled to the brim with college students - so lots of eye candy. I highly recommend the Isabella Stewart Gardner Museum if you choose Boston. While the South End is 'a gay mecca', Boston does not really have a true gay ghetto like Boystown. 30 years ago, The Fenway was close to being a gay ghetto, but that has changed.

Chicago also has great museums, and lots of public art. I prefer the gay dance clubs in Chicago to the one's in Boston (not part of your criteria). The boyfriend and I encountered no negative reactions while walking around hand-in-hand at Museums, on the subway, or in downtown Chicago. However, we did not see any other obviously gay couples outside of Boystown.

I think you would have a great time either place.
posted by hworth at 8:13 AM on July 29

The boyfriend and I encountered no negative reactions while walking around hand-in-hand at Museums, on the subway, or in downtown Chicago.

I'll second this, because Chicago trends towards a laid-back, Midwestern live-and-let-live acceptance, despite outsiders' misconceptions that it's a city of farmers. Bostonians, even though they live in super liberal Massachusetts, always strike me as deeply unfriendly no matter what your sexual orientation, but I doubt you'd encounter any manifest hostility from the uppercrust citizenry. I'm biased, though, because I'd step over my dying mother for a weekend in Chicago (for its public art, green spaces, architecture, theater hotspots, nice people, and gorgeous weather outside of winter) and find many New England city attitudes very grating.
posted by zoomorphic at 12:34 PM on July 29

I would actually recommend Minneapolis over Chicago if you go with the midwest, but I'm biased because I grew up in Chicago and just hate the place on principle. There are plenty of gay bars in the city, an art movement rivaled only by New York City and a very strong central network concentrated on being gay-friendly. Also, you would have more fun on less cash depending on where yo ustay.

Otherwise - Boston. But that's just because that's what you asked and I hate Chicago.
posted by medea42 at 2:57 PM on July 29

Thanks to all for the great answers so far!
posted by sevenyearlurk at 5:02 PM on July 29

The Andersonville neighborhood in Chicago is another very GLBT part of town, and trends older and more settled than Boystown. Some really great food and fun, neighborhoody bars, too.
posted by me3dia at 8:36 PM on July 30

In case it's not clear to someone from out of town, Boystown, Andersonville, and Uptown in Chicago are all adjacent neighborhoods. They're probably a 20-40 minute L ride from the big museums and milenium park.
posted by garlic at 1:17 PM on July 31