Make sure you're under 5/24, or you won't be approved. Make sure you haven't applied for any other cards with Chase in the last 30 days. Chase has a 2/30 rule that's not always enforced but can be the basis of denying you for having more than 2 personal credit card applications in 30 days.
Apply for the card you really want first, get it approved. Apply for the second one with another browser, or clear your cache and cookies, or use incognito mode, and get it approved all on the same day. You don't want your browser data to confuse Chase's system into thinking you're submitting duplicate applications that'll result in dumping one. Call recon if not automatically approved. Approval of both must be on the same day! Use a referral link if you can.
Yes, charges made on MagicBand to your room count as "travel," earn 3x UR, and qualify for the $300 travel credit if you pay off the charge at the hotel's front desk with CSR.
GOOD LUCK!