Originally Posted by
18sas
Depends due to the change fee. If each way is less than $200 then you'd be better off with them separate if you have to change one direction. Of course if you have to change both directions, then you'd worse off. If each leg is < $100 then it's a no brainer to book them separately.
Also, OP, the day before Labor Day is probably like Thanksgiving Day. Try booking a flight anywhere after noon, the options are slim to non-existent.
Another consideration is schedule changes: with two OWs and a significant schedule change in one direction only, it's more difficult--but not impossible if you HUCA--to totally cancel for free than if you have a RT.