[Gunner]

So, as part of my work (international organisation) we could have our next workshop/conference either in Montreal or Chicago. These are all day long events and then some tourism, eating and just a little bit of party.

I have an important vote, therefore, from a tourism standpoint, my vote goes to Montreal or Chicago?

Is in the summer so weather should be no problem.

[WestCoast]

Chicago not even a debate unless the conference is several weeks long.

Montreal is not easy for a couple days, Chicago would be easier.

Also you're going for work the chances of contacting big hitters in Chicago is much higher than Montreal.

Personally been to both cities for your set up it's a no brainer to do Chicago.

[Rutting Elephant]

Chicago Latinas were so open to approaches ten years ago when I lived there. Even if they all have Iphones now, I'd go back there over the Northeast US.

[Gunner]

The agenda is planned for 4 days, with some "gala dinner", "cocktails", "working lunches" and "tourism" thrown over. We are looking at a 5 day trip I guess.

[TheChi]

I'm a bit biased but for an event like this I think Chicago wins. Some of the best restaurants in the world, tons of art, culture, sightseeing, you have boat cruises on the lake, amazing art museums/Shedd Aquarium. Tons of neighborhood street festivals too, could do a Cubs game rooftop if they're in town and then go out afterwards and see tons of friendly drunk girls.

[WestCoast]

@ bars yep in that case would go to Chicago nail in coffin is the 5 day constraint. Montreal is a beautiful city with banging girls but you're gonna have a hard time converting because you usually need at least 2 days... While juggling a conference? Best to shoot for snls.

[philly22]

I like both cities. Its very close but I'd lead toward Montreal

[chyamor]

without dates any info on here is useless

you need to compare whats going on .
Lolla, jazz fest, f1, wavefest etc

[MrRoundtree]

Stay away from Montreal during winter..city isn't as hot (same for women)

[zatara]

Chicago in summer is great: nice bars, any shops you could want, a passable beach on the lake. It's my favourite 'big' American city for the combination of work possibilities and play possibilities. As long as you're not there between October and April anyway.