nelsonkg - have you tried Delta out of Providence - they are listing flights for cheaper than Southwest in May. I just put in May 21 thru 28 and they were cheaper. Also not sure where you are but Delta out of Hartford if really reasonable now. We got ours for $189/person including taxes and fees and they are still reasonable for May.
momtoleasawav - same with you. Not sure where you are in Mass but Delta out of Hartford for the Easter week (leaving that Sat. and returning the following Sat.) is coming up with $1150 for 5 including tax/fees.
Not sure of any of the dates of your trips but it may be worth checking out other airports. Southwest out of Hartford has been more expensive than Delta, even when you add in any luggage fees.
I've been flying Southwest pretty much exclusively and found that they have changed their pricing strategy. When fares first open up they now seem to be priced higher and go down as time passes. Southwest in the past always seem to post their lowest rates from the start.
Keep checking the fares. My trip for March came down a whole lot (from almost $300 each way to only $111 each way now.)