Hello,
I think you have the makings of a strong application. Love your leadership experiences and ECs.
Two main thoughts for you:
Here's how I look at your GMAT score. It's one of the few things (along with your essays, your interview, and sort of your recommendations) that you can still impact in your application. Everything else -- your work history, your undergrad transcripts, and most of your ECs -- are set in stone at this point. While a 690 certainly isn't so bad that it would definitely keep you out of those schools, why not take another shot at improving your chances if you can. You still have a lot of time before the Round 1 deadlines, so if i were you I'd consider taking one more shot.
Even better would be for you to NOT work on the GMAT and your essays at the same time, and to push back your apps till Round 2. Applicants usually sigh when they hear that, but there's no real advantage to applying in R1, and even if you believe there is, wouldn't you rather apply in R2 with a 720 than R1 with a 690? I'd rather than you did that. Yes, 30 points isn't a lot, and adcomms will tell you it doesn't matter, etc., etc.... But what if you don't get in with that 690? Do you really want to be wondering in five months, "Maybe I should have taken the GMAT again."
Applying to FIVE programs in January will be tough, but it can certainly be done. Assuming you take the GMAT again around October 1, that gives you a TON of time to work on those five apps.
Also, re: your target schools, why PT for Kellogg and Booth? I'd say go FT for all or PT for all... To split it seems odd to me.
Good luck!
Scott