How to impress a New Yorker who wants to experience “real deal” Chicago?

I’m trying to impress someone (that I like like) who is visiting me for a week next month and he is a native New Yorker. He has been here before and done all the touristy things. He told me he wants me to show him the “real deal” Chicago. I’ve lived here for a total of 10 years so I have a few ideas food/drink wise but would love others’ input! Here’s what I’ve got:

Superdawg
Red Hot Ranch
Jibaritos y mas
Margie’s Candies
Richard’s Bar
Whirlaway Lounge
L&L Tavern

Also not at all against pricier places as long as they have that ~classic Chicago~ vibe!

Edit: thank you for so many great recommendations and reminders of great places I love! I feel like I should clarify it’s more about me wanting to impress someone I have a crush on that likes these kind of places than converting a New Yorker or proving anything— he already loves Chicago :)