He's fine flying there with you, as you are the rated pilot that meets the qualifications.

Besides the opportunity to say "I did that," it's really nothing special, I've flown for 10yrs and I've been in there once.

If you want a challenge, and an airport that will let you in easy, just go to Midway when a huge arrival push is coming in. Prepare to land on 31L(My favorite side-walk.......er runway). Be prepared for anything.