1. The last time I had been to Chicago was four years ago.

2. The last time I have been to Chicago was four years ago.

3. The last time I was in Chicago was four years ago.

I know that the first one is correct, though I'm not completely sure why. Why the past perfect tense is OK? I suppose that it's similar to:It's the first time I have been... It was the first time I had been (one tense backwards). Am I right?

No. 2 I suppose is incorrect because "ago" and the present perfect tense do not go hand in hand.

No. 3 I would say it's alright. What do you think?
1. The last time I had been to Chicago had been four years ago. [but was is accepted by some
He's looking from a past point of reference to a more distant situation. Now you have to think about it, I won't tell you more.
118 on "The last time I had been to"

Let's Roll!: Ordinary People, Extraordinary Courage - Page 265

by Lisa Beamer, Ken Abraham, Betty Robison - Biography & Autobiography - 2002 - 317 pages

The last time I had been to the Newark airport had been September 10, when Todd
and I had returned from Rome. The day we departed I had dropped off Todd and ...

Students: Are you brave enough to let our tutors analyse your pronunciation?
2 wrong
3 OK
Hi Marius

So, actually, I was right that 1 and 3 are OK.

thanks [Y]