First, congrats on these options - fantastic results.
It's obviously tough to tell someone where they should go without knowing what makes you tick, what you want for your career, etc. All I can probably do that will really help is tell you how I view these schools for strategic purposes entering the application process, which will probably carry over a bit.
With Chicago, I'm sure you know all about finance, flexible course work, etc. But the big thing about Booth is that there is an "edge" that is really good and healthy, but present nonetheless. There's a spirit of challenging yourself and raising your game that you don't always see in a b-school. The best thing about Booth is how social it is has become - with the Harper Center coming in a decade ago and then the South Loop providing a residential community - so that compliments the more competitive streak.
With Tuck, you are looking at more of a "summer camp" vibe in the way everyone connects and really dives into a collaborative experience. It's almost a cult, in a good way. Tuck has underrated ties to cool industries in NYC and I think it does the best of blending theoretical (case method) and practical (experiential) learning models. It's small and way the hell out there, but you can't really get a more intensely personal and connective experience.
So it sort of comes down to whether you'd rather have collaborative with a dash of big city competitive edge and brain-stretching, or you'd rather have collaborative with a healthy scoop of fun/friendly.
Both schools are amazing, both have big university brand names, both are among my very favorites. You honestly can't go wrong. If it's about something personal - geographic employment considerations, industry, so forth - I have no idea, obviously. But for culture considerations, see the above.
Hope this helps.
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