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Price drop and price match on vacation packages

yvonnenguyen
Explorer C

Does anyone know what the best times are to book a flight to Boston in January? I know that Boston gets the coldest in January so I was wondering if Southwest tends to drop ticket prices to Boston in January in order to get more people on their flights. I'm planning to fly anywhere from January 9-11.

 

Also if I book a flight and hotel together, does Southwest still offer price matches for the hotel even though it's technically discounted through a vacation package if I end up finding a lower price for the hotel on a different website? If not, would it be better if I booked flight and hotel separately?

 

Any help would be greatly appeciated. Please let me know as soon as possible. Thank you!