Is it legal to book 2 different flights; 1 earlier & 1 later?

Upvote:4

It's not a question of legal, but what the airline allows, and this is often not permitted. For example, United's contract of carriage says:

The types of improper reservations that UA will cancel without notice include, but are not limited to … reservations made for the same passenger on flights traveling on or about the same date between one or more of the same or nearby origin or destination cities; and reservations with connections that depart before the arrival on the inbound flight.

The airline's revenue protection system may automatically cancel the duplicate booking at some point.

Also, if you have checked bags, they won't follow you to your second booking.

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