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So on Monday June 30th, we have a Seetickets Coach departing at 2:30 in the afternoon from the festival to Bristol. Looking into taking a flight out of Bristol airport that departs at 6pm. Assuming we get a timely taxi/uber from the coach dropoff in Bristol to the airport, would this be a reasonable itinerary? Or high chance of not making the flight?

Yeah, I can confirm having seen them in 1982

Is there a chance they moved the dates just to book Billie Eilish? she is in Barcelona on 14 and 15 of June...

Both are headliners clearly. 

Yes, but take a look at last year program: https://opener.pl/program-2024 The headliners are ordered by date. Now, Linkin Park are the first name, even though they’re playing the last day. That's why I think LP are the only headliners for now. You may be right about NIN co-headlining (although I think they are still trying to get Olivia for that day). Also, I think Gracie is not co-headlining, it would be stated in the announcement.    Anyway, the lineup is really strong and there are still around 20 international names to be added. May be one of the best editions in the festival’s history.