Are you dead-set on carrying your goodies on the plane?
You can ship Portillo’s, Lou Malnati’s, Eli’s Cheesecake, and other Chicago staples anywhere in the country at the Tastes of Chicago website.
I don’t really know if taking an Italian Beef through security would be an issue, but I also don’t know how well it would hold up until you got it back home to your friend anyway.
If you’re flying out of O’Hare, there’s an Eli’s in Terminal 1, and Pizzeria Uno locations in Terminals 2, 3, and 5, past security.
I take my siblings Frango mints, which they still associate with Chicago though I think they’re made somewhere else now. Garrett’s popcorn would work as well, I’d think.
I’ve never gotten Garrett’s Popcorn’s popularity. I know ex-pats love it, but the two times I’ve had it I’ve been like “eh, it’s caramel corn.” I had family here for the Taste last summer and they noted the HUGE lines that are always coming out of the place, and I told them it’s crazy popular with people that visit. They got some and had the same reaction as me. It’s good, but not “when I’m in town I’ve gotta get some” good.
If I left Chicago and returned, I’d be looking for a Portillos.
It is possible to take Lou Malnati’s frozen pizzas on the plane. All the carryout locations sell frozen 10 inch and 6 inch pizzas, and they will usually give you an appropriately sized box carrier thing if you ask nicely (I used to work at one). The pizzas take a long time to defrost and will be perfectly safe to cook and eat after a couple hours flight.
Oh hey, look at that! I forgot to return to this thread. I am going to blame lots of great beer and late nights in Chicago bars. Does that get me off the hook? (ETA also there was the Ouzo night in Greektown)
I took home Vosges chocolates both for my chauffeur friend and for my husband. Well received all around. Very good chocolates!
Oh man - I wish I had thought to look for giardiniera so I can make Italian beef at home.
My main (humerous) concern taking an Italian Beef through security was whether the wet bun would be considered a “gel” and violate the 3 oz rule.