Current student here.
Most people will be happy in any dorm. Stereotypes are stereotypes, and turnover can be upwards of 50% a year in some houses, so house/dorm culture can be difficult to predict. I would put must-have amenities ahead of house culture, because these things are known quantities - and I say this as someone who loves house culture.
If you’re an athlete, you will probably want a dorm near the gyms - North/Max/Snitchcock. Walking half a mile there and back from B-J/South/I-House (or a mile if you’re in Stony) isn’t much fun in the winter.
AC (which B-J/Snitchcock don’t have) is largely a nonfactor. 90% of days when you’d need AC occur outside the academic year. In the winter, housing cranks the thermostat waaay higher than it needs to be across the board (I actually have to crack open a window to stay cool in December) so the cold isn’t a concern either.
None of the dorms have a direct connection to a dining hall, but the walk can be anywhere from 10 yards (South/North) to 1/2 a mile (I-House) or a full mile (Stony - this is why many Stony residents cook in their apartments). Snitchcock and B-J are somewhere in the middle - each less than a block from the nearest source of food.
North has dedicated study spaces, as does B-J; I’m not sure about other dorms, but the house lounge is always a possibility (albeit with a high risk of distractions).
Fraternities are mostly near North and Max, if you’re into that kind of thing.
The CTA is most accessible from North (the 55 bus will take you to the Red/Green lines) or Stony (the #6 can get you downtown in 25-30 minutes). B-J and South have the 59, which can get you to the Garfield Red Line, but that only runs on weekdays for some reason. The 2 goes straight from B-J’s door to the Mag Mile (again, only on weekdays) while the 171 and 172 ferry students from campus to stores on 55th and/or restaurants on 53rd during the day. The CTA is great in general - the U-Pass delivers more bang for your buck than anything else the University requires you to pay for.
If you want to go to a lot of trendy shops/restaurants, those are mostly up on 53rd Street, but the CTA and campus shuttles make the distance mostly a nonfactor. Woodlawn (the area south of the Midway on paper, and south of 61st Street in spirit) is relatively underserved by campus shuttles because A. there are fewer amenities in the area and B. the administration tries to keep Suspicious Black Males out of Hyde Park - poor nonwhite folks might scare parents or (more importantly) prospective parents. So living nearby is a better bet than shuttles if you’re the activist type.