Hi Yes, this would be quite simple but
1. You should import all your Cities first (not customers)
2. As you import your customers, you would be able to build a very clear (yet... formatted needed) json to bind it to the values in your City
I realize that looks like super easy, and per se it is, but the important thing to note, is that you should always create the lookup"ed" to first.
so like if you have ice cream flavors and then Kids linked to their favorite flavors. same thing.
Create all the possible flavors (or add new ones)
Then insert the children, then you can use an action to grab all the records(rows) in the City (aka flavor) columns that match for that person (aka child), and then populate that column at the same time you create the Person.
so yes, completely doable.