Congrats on a bunch of great options and all the detail about your goals and thoughts at the moment. I wanted to chime in and represent Booth here as I think some of your perceptions are a bit off. While Booth is certainly strong in IB and quanty finance roles (nobody really goes into risk management but strong recruiting from funds such as DFA and Thaler Management), you're missing a ton of areas where Booth excels and we're MUCH more than a finance school. Booth does extremely well in consulting and (not my area but I think McK alone is hiring ~50 students or almost 10% of the class) tech (Amazon wants to be Booth's #1 employer this year, lots of traction at other big tech companies). The school is also super well connected in the VC/PE world (both in Chicago and on the coasts) and has a strong reputation with employers.
In terms of culture, I can assure you as a second year that Booth students are anything but nerdy and likely an issue of the small sample size you mentioned. Like any school, there are going to be some people that are very outgoing and some that are not as much, but it's very easy here to find the outgoing people if that's what you desire from your social life. 50% of us live in Millenium Park Plaza (MPP) in the Loop and it's predominantly the very social people so by living in the building, you'll be surrounded by these types of people constantly. Also regarding CBS, keep in mind that the cost of living is significantly higher in NYC than Chicago so the additional scholarship is essentially a wash.
Given your goals, I think Booth is a great fit for you. The school is really focused on entrepreneurship and many say its the hidden gem of Booth. New Venture Challenge was named the #1 accelerator in the country (overall, not university) and was the birthplace of Grubhub and Braintree. There are also a ton of labs where you can get hands on experience in VC/PE, startups, etc (
https://www.chicagobooth.edu/programs/f ... emics/labs).
From a rankings/prestige perspective, Booth has a bit more than your other options as the school is pretty firmly in the Top 4 and more or less equivalent to Wharton (#2 ranked in USN, lots more cross admits choosing Booth over Wharton than in prior years). Booth also has a ton of upward momentum and is not going to be slowing down anytime soon.
You're clearly very bright so at the end of the day, you'll likely get where you want to be from any of these schools so this should mostly come down to fit. Hopefully you're able to make it to all of the school's sell weekends as that will give you the best sense of what each school is about and what life will be like there. I was deciding between similar schools myself (and had some of your reservations about Booth given my limited interactions) and was blown away after First Day and knew Booth was where I wanted to spend the next two years. Best of luck wherever you end up and feel free to PM me with any Booth specific questions I didn't address here.