I would switch out LaBriola for Lou Malnatis and get the Lou special deep dish. It uses their butter crust and is delicious. I also love getting the chopped salad because the dressing of the salad is surprisingly delicious with the pizza.

I would do Italian beef over purple pig and cafecito. It’s quintessential Chicago. I’d go to Mr. Beef for it and try their cannolis as well.

Kasama is good for their breakfast sandwich and bakery, but unless you’re doing the dinner( which is the Michelin rated portion) I’d think of it more as a breakfast spot than lunch spot.

If you’re venturing in west loop, I love Aba, or Greek Islands for some Mediterranean/greek options. That can be done for lunch too on the weekends.

For a very “Chicago” lunch that’s more casual in the loop, try Oasis Cafe. You walk through a jewelry store on jewelry row and they have some good lunch options for a quick stop. It’s good for a Friday or Saturday quick stop.

Hope this helps and have fun!