Mary

NYC!!!!!!!!!! Hands down!!!! I have not been to Boston yet. My mother has been several times but she prefers NY. NY and Chicago can be oppressingly hot in the summer. Boston, in theory, is cooler...sometimes. I would not go in July or August. Stick to June. Also consider this, Boston is one of the oldest cites in the US and so is NY. Chicago is newer thanks to Mrs. O'Leary's bovine. Nothing pre-dates the fire. It will really depend on your interests, but if you have never been to NYC you must go, no question.

ROB

The answer is simply New York! Lived in both Manhattan and Boston, and have visited Chicago several times. But, to choose one place to see for first time, NY is in a class by itself as far as U.S. cities go. Also, it is more fun that you are young and don't have kids yet. No question, NYC!!

Lisa

I've been to NYC several times for long weekends but never in the summer...it's a great city (shows/restraunts/museums) BUT after visiting Chicago last spring, I was really impressed...the city is MUCH cleaner and really seemed progressive...we're from the Baltimore/DC area and I think we are way behind the times...I personally think 5 days in either place might be a little long especially in the summer) but I think there's a greater possibility for day trips if you go to Chicago...I'd save NY for the long fall/winter weekend getaway...have fun!