Welcome to GMAT Club (i have moved your discussion to a better forum).
I have strong respect for the Booth program - it has done very well in terms of being a finance hub. Despite ranking as #1 last year and #2 this year in BW rankings, it still does not have the ring of H/S/W, but things like that take time, and if you live in Chicago, Booth and Kellogg tend to dominate the city, and you can get pretty much any door open for you there. I also like Chicago a lot more than Philly, as a city to work, live, eat, etc but that's personal and not key as you said.
There are stereotypes about programs such as Wharton is always better than Booth or that Booth is too theoretical. I am not sure how accurate that is for their EMBA program or with the wide choice of classes both offer and frankly, Booth has been beating Wharton in the last few years in terms of rankings.... The person you are talking to may be thinking about Wharton from 10 years ago.
I would do my own research, as well as look back at what is driving for the EMBA decision.... and consider that being close to your EMBA network will be helpful. You don't want to be flying to the west coast for example if you plan to stay in New York since many people end up networking and getting jobs through their EMBA classmates.
Back to Wharton, consider the GMAT requirement and whether it will be a considerable battle to take it. You can take it one thing at a time and if you are already familiar with EA, perhaps it is a short prep period for the GMAT. The GMAT does put more requirements on the candidate, but it also makes the school/program harder to get and more selective, which usually drives more commitment from the applicants and more bonding among the students as misery loves company.
P.S. Sorry about the WL process. That is annoying and many schools seem to have a mind-set of a one-season-lifespan. They think people only consider them for a season so they can be very last minute about their decisions. True of FT and PT programs alike. It is not their fault per se, but rather the system in general works this way, esp if they do not lack applicants, and only a number of schools that actually stand out and make the WL process more humane and don't make one feel like a second class citizen. I have seen a number of people on GMAT Club reject much higher ranked schools simply due to the WL management process.
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