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Kettle Moraine, WI | Book direct flight directly with the airline as many said is best.
Airport and airline will be more dependent on where getting to and how getting from airport to the ultimate destination.
As a first time flyer i would suggest they try to fly carry-on only (and make sure bags meet the airline dimensions and their ticket allowance) if you want to keep it non complicated, having to find and get luggage after deplaning can add a bit of stress being in a new airport and first time flying. Keep the process smooth with less friction.
Consider business class if money isn't a big deal for this one off event. Wider seats, maybe more carry-on allowance, easier to find seat and settle in with earlier boarding group. A little bit extra service in that cabin may relax in the flight.
Give enough time before flight at airport to navigate the place where to go and the process. If have trouble this can limit stress and risk of missed flight.
And if this person does not use a smartphone, other mitigations may be required. (Ground transport, hotel checking and most importantly dealing with any changes of itinerary weather forced or voluntary)
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