Great question — answering as the UphillTech team:
Sure this can be done: have a look to azair which has very powerful search options (see the advanced options), including choice of return and departure day , length of stay, period within which the trip should happen and a range of departure and arrival airports including "take me anywhere." A similarly powerful search option for the anywhere part is kiwi.com . Note: much of this is copied from my own answer here , plus you might want to take note of this overview of flight search engines I once composed .
Full answer by mts: https://travel.stackexchange.com/a/82061 (CC BY-SA 3.0).
Need it done for your business? UphillTech.
