Can you book 2 Southwest flights at the same time?

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My daughter’s school marching band has been invited (accepted?) to play in the Thanksgiving Day Parade in Chicago this year.  They are driving up during the week and returning back immediately after the parade.

Of course the travel hacker in me doesn’t want to bother DRIVING from Cincinnati to Chicago – that’s what I got all these points for!  I am not allowed to fly her to Chicago – the package for the school says that they all have to go together on the bus.  But once the parade is over, they are released to parents and then we’re free to do whatever we want.

Travel Hacking the school trip – hotels

First off, I immediately booked 2 nights at the Sheraton Grand Chicago, which is the hotel where everyone is staying at and is within a mile…

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