I was raised in Chicago, when we go back our culinary checklist is pretty low rent, but it’s stuff you can’t find anywhere else. There are multiple good sources for any of them (competition is fierce) so just ask a local. If you’re a vegetarian, I can’t help you:
- Italian beef w/sweet peppers (get the hot “sport” peppers if you like it hot.)
- Chicago hot dog “all the way” (warning: do not request ketchup or you may be asked to leave)
- Pizza, the thin crust variety, with good sausage - not the thick crust stuff (we always called that “Sicilian pizza.”)
Even if you’re not a baseball fan (arguably, the Cubbies are marginally a baseball team) hanging out at the Cubby Bear across the street from Wrigley on a game day is the ultimate people watching experience. If you can do a game, even better.
The architectural tour via the Chicago River is a treat. (Moon the Trump Tower for me.) The museums are excellent, especially the Field Museum, but unless the weather is bad, I would pass, as it take a full day to explore each one.
Definite NO to Navy Pier. Touristy.
Millennial Park is great, gotta get the standard “bean reflection” picture. The entire lakefront is great for walking around.
The view from the Hancock Building is better that Sears (or whatever they call it now.)
There are many great neighborhoods, not sure what the current “hip” ones are but it’s fun to check them out. There is great shopping to be had everywhere, depends on what you’re looking for.
The drive south on LSD (Lake Shore Drive) if you’re coming from Evanston to downtown is lovely.
Yes to Second City in Old Town.
Lot’s of great music, Of course the blues clubs are legendary, but the Irish music scene is big in Chicago and the pubs are a blast.
Have fun, best thing to do is to not overplan, let the good times roll.