Originally Posted by neuron

A couple of questions for the OP, so to better gauge the interests.

Are you more concerned about arts/culture, museums, music, nightlife, bars, food, outdoors/nature?

For DC, amongst the 3, it has the best museums and some great outdoor areas. July will be humid, which is much more oppressive than ORD or YYZ. I am in DC every July/Aug for a couple of days and its my least favourite time to be there.

For arts/culture, I would rank Toronto higher than ORD or DCA because of the theatre scene. I used to live in Toronto and the indie music set was top notch! Chicago, of course has its high lights in this respect also.

For food diversity, it does not get better than Toronto, esp for Chinese food. The food scene is very vibrant. Chicago may have some moments (deep dish pie/pizza, steaks), but overall, Toronto has the variety. I am less impressed with DC wrt to food.

For outdoors, the summer is a great time to visit Toronto and Chicago. A couple of hours outside of Toronto is the Niagara wine valley and the Falls.