So there is a BOS to DTW fare that is pretty consistently available with 0 advance purchase for about $165 or so o/w. You can def get 2 segments, but not sure about 3.

So for example, tonight Tue Dec 1 or Fri Dec 4 I could "go somewhere," but not sure other than the DTW if there is any other good fare say $75 a segment or under, approximately. The problem with DTW is especially for a morning return, it takes time to get back to the east coast. I don't think RIC has as attractive fares as it once did, I think those were fuled when B6 entered BOS RIC but the fares may have stabalized.

One thing I could do though its very costly is fly to BOS, LGA, DCA leaving at 7PM, and I could still get back in the morning for work doing the same kind of routing, and those flights are just so quick! Just curious if I am missing other cities to look at for a similar run on the east coast.

Other than using ITA for nearby airports, are there other tools you like to use? For instance can Google flights say find the least expensive city to fly to say tonight or Friday night out of BOS or another city?

I booked that LGA fare RT for about $112 for nearly each day it was offered. Also I have a couple of similar trips after work from BOS to PHL.

I did see that B6 has a sale today so I want to check e.e. JFK, BWI, DCA, etc.

I think I gravitate to this approach because I live and work about 10-15 minuts from BOS, so I mean, if I go somewhere after work tonight or Fri, I wouldn't really miss much and I'm still around during the day.