Neither club is in the Champions League nor Europa League this season so they are discussing playing a lucrative one-off game, almost certainly in the Middle East.
AC Milan's director Umberto Gandini confirmed a friendly with United was on the agenda.
Gandini said: "This is something we have been talking about for a few weeks and we have a committed interest to do something together.
"It's just a question to find the right date and then to find the right place."
One possible date would be around Wednesday January 28, which does not clash with any European matches, and Milan coach Filippo Inzaghi does not have any Italian Cup games to contend with.
There are Capital One Cup semi-finals taking place but that would not impact on United playing a friendly.
In 2008 a full-strength United squad played a testimonial game in Riyahd, Saudi Arabia, in front of sell-out 69,000 crowd on a Monday night and then had a spell at a warm-weather training camp before returning for an FA Cup match.
Van Gaal said earlier this month that he wanted his team to play top teams in midweek and had spoken about it to United executive vice-chairman Ed Woodward and managing director Richard Arnold.
Van Gaal said: "I like to play midweek games against high-level opponents."
Both United and Milan could expect to earn more than £1million from the match.
United expect a drop in income of up to £48million as a result of failing to qualify for the Champions League under David Moyes.