Wow, congrats. You have two wonderful choices. Most would be envious to be in your shoes. You can’t go wrong with either choice. Let me give you a few of my thoughts:
For finance, there is no better place that UPenn, particularly Wharton. The other UPenn colleges do well in finance recruiting as well (CAS, SEAS, etc). I know a few of my son’s friends who attend UPenn and love it. One thing you should consider is that recruiting at these schools are a highly orchestrated affair, and coordinated by the Career center. Some firms (particularly PE shops) will go as far as to extend their invites to info sessions for Wharton kids only. These are only a handful of the most competitive firms though. But you should keep this in mind. If your ultimate goal is to transfer then keep in mind that the process is competitive, but I’ve heard its possible. The location, collaborative attitude and resources at Penn are excellent.
UChicago has a more well known Economics brand. If you’re interested in a PhD, I’d say that UChicago is a better choice. Econ at UChicago is essentially high level math. Most of the students who are interested in an Econ PhD are encouraged to get a math degree instead. The different Econ tracks at Chicago offer some flexibilty, and as you mention the Data Science track is quite appealing. UChicago only has one college, so the recruiters cannot restrict who they interview. The administration is trying hard to shed the image of ‘where fun goes to die’, and they have made great efforts to make Chicago a more appealing place: more internships, more career counselling, reducing the core load, more focus on house culture, etc. So the UChicago of today is a lot different than it was 10-20 years ago.
In terms of finance placement, both schools publish their results, so its easy to compare what % of graduating seniors go into financial services or consulting:
Penn CAS (2017): 18% financial services, 18% consulting
Penn SEAS (2017): 14% finance, 11% consulting
Penn Wharton (2017): 50% finance, 20% consulting
UChicago College (2017): 33% financial services, 12% consulting
https://www.vpul.upenn.edu/careerservices/surveys.php#Undergrad
https://collegeadmissions.uchicago.edu/files/documents/class-2017-outcomes.pdf
If you want to go into finance or consulting, then Wharton is clearly would be the best choice. But if you are not able to transfer to Wharton, then UChicago undergrad does a bit better in terms of placement. Keep in mind that this is like comparing oranges to apples, as these stats only list the % who entered the field, not the numerator and denominator. But this will give you a general idea. Both universities do well for finance/consulting, and again you can’t go wrong.