Spiaggia for Italian food. Little $$ but worth itHey Chicago fam, any can't miss places to eat while we're in town? We're staying near the Magnificent Mile, planning to go into the loop on Thursday. Saturday is Cubs game so we'll be up that way most of the day. It's probably verboten but Giordano's is on the list somewhere as I got to get some Chicago style while I'm there.
Benny's Chop House for steak, though you are from Dallas so you may be good on steak.
Lou Malnati's for Chicago pizza
XOCO for lunch, though again, being from Dallas, your Mexican food is probably better than ours.
DMK for burgers is my favorite but also check out au Cheval (or sister restaurant small Cheval in the loop).
Untitled Supper Club is great if you are looking for a speakeasy
And you should 100% do an architectural tour on the river before you go (if the weather is nice).
Let me know if you are looking for anything more specific. Also feel free to DM me.