An early strike from the teenage winger Jesus Corona and two second half goals from Cesar Delgado sealed the victory for Monterrey against Ulsan Hyundai in the quarter-finals.
Interim Blues manager, Rafael Benitez has taken a full-strength squad to Japan, with Fernando Torres, Juan Mata, and Frank Lampard flying out ahead of Thursday's fixture.
On the other side of the draw Egyptian side Al Ahly have progressed into the last four after they beat Japanese champions Sanfrecce Hiroshima, 2-1 and they will face Brazil's Corinthians, current holders of the Libertadores Cup.
“We [Liverpool] played the final in Japan in 2005, we won two years ago [with Inter]. It was a great experience for me and hopefully it will be a great experience for our players,” Benitez told reporters.
"It's important always to have these opportunities to win any trophy, and especially a trophy like this one.
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"It will be a fantastic experience. Yes, we are concerned because we know it will be very difficult, but we are working very hard trying to organise everything properly.
"Maybe it will not be ideal because you don't have too much time and you have to go and you have to play a game in three days' time.
"But we will try to do our best, obviously. It's not easy. The doctor and the fitness coaches are a little bit crazy now, but we will try to do our best."
As well as a place in the final being up for grabs, the semi final will also give Chelsea a glimpse of the Hawk-Eye and GoalRef goal-line technology which is set to be introduced to the Premier League next season.