How do you figure out this ';Traveling Game'; thing?

All my friends know how to do this weird puzzle thing and it pisses me off. One of them tells us to pick a city and then they tell the other one some random stuff and the other one comes up with the same city.





For example: we said Chicago and then one said...





We're going to Compton for 5 nights then Boston Then Sacremento.





And then the other one said Chicago. How the hell do you do that?How do you figure out this ';Traveling Game'; thing?
*plan ahead.* They do it behind your back.

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