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What is the best time to leave hotel Bourbon Orleans for a 5:30am flight domestic

How to get from dropoff point to airline gate?
Call your airline to request wheelchair service.
I am so grateful to a fellow named Wyman who helped me navigate security and get to my gate during a recent flight out of MSY. He was so nice! He even stopped by to check if I needed anything during a six-hour wait for my flight. He was just such a really pleasant, courteous and kind man.
I will arrive at MSY on Southwest Airlines at 12:30 PM on Dec 3, and a friend will be coming in on United Airlines from Newark and from Nepal that day at 10:39 AM, so I think this is two different concourses that we arrive in. Rather than have her wait for me at my baggage claim area is there an easily found restaurant in a part of the airport that she can get to after picking up her bag? And is there free wifi available? She will have a laptop but no operable telephone.
I need help with a skycap to take my luggage from taxi to check in. Do I need to schedule this or give notice before I arrive?