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Which program should I choose?

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Midwest6
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CobraKai
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CobraKai
With Kellogg, Booth, and Ross

Dont forget about Mendoza and Kelley.
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Kjar
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Well, I guess you applied acknowledging that there is a huge chance you'll have to finance the whole stuff out of pocket... So why it should be your first consideration?

My vote is for Ross.
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I understand where you're coming from, but seriously it would be Ross.
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I didn't apply to Ross, but all the schools I applied to include health benefits when you enroll. I believe all grad schools do.

Ross is a much larger program--this is worth thinking about. I just looked it up at it's 5 times the size (1000 vs 215). That is a HUGE difference in culture.

I'm with Cobra: working during business school sounds horrendous. If you could negotiate that away, perhaps, but I'd rather spend my time attending recruiting events, leading clubs, and networking.

Can you talk to other admitted students and see who you connect with more? Reach out to alums and current students as well in your target area. Finally, talk to the career center people. That was the most helpful thing I did when deciding. They are a wealth of information!

If you have these chats and decide that Wisconsin is just as good a fit as Michigan, then enjoy. I think you may end up being more impressed by the Ross people in the end, but god speed either way.
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I agree with the overall trend of this thread. I tend to view schools in competitive clusters based on companies that recruit there and consensus rankings. Within a cluster I think people should go with the school they fit best with, regardless of actual ranks and at times money can make a difference. However, I would not put Ross and Wisconsin in the same school grouping.

If you are recruiting for IB, I would say that Ross gives you the opportunity to go to New York (or anywhere) whereas at Wisconsin you likely will have to be in Chicago, where frankly there are much fewer opportunities for banking, since Wisconsin is a much more regional business school. Like people said, you will also be competing with people from Booth and Kellogg that want to stay in Chicago, as well as people from other schools that can make a solid case for going to Chicago (i.e. they are from there originally). Ross puts you on equal footing in Chicago whereas Wisconsin does not, and opens up more national opportunities.

I did IB recruiting this past fall in New York and at multi-school networking events hosted by companies I did encounter folks from Ross...I did not see anyone from Wisconsin to be honest. That's not to say that you can't get NYC IB from Wisconsin, but I would pay special attention to the employment report and even try to reach out to alumni to gauge the feasibility. Based on my brief knowledge of the schools, it seems a much more difficult task from Wisconsin.
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I think everyone here is on the money. Since your goals are quite specific about wanting to move into IB in Chicago, you should definitely speak to recruiters, career center, alums and current students who want to pursue similar goals.

That said, I think having that Project Assistantship and stipend on the resume could also help; but on the other hand, it could eat away at some valuable time during your MBA (recruiting, networking, groupwork etc.)

Good luck!
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Just a current Wisconsin student chiming in here, I have full scholi due to project assistantship as well and 13 hrs is overestimated. It's some kind of requirement to call it 1/3 of a 40hr work week, really it's much less. And it's something to put on resume to brag about. Plus might want to think about being able to freely choose what you want to do when you graduate and not on chasing the paycheck to make payment on that 100k debt you incurred.