Yeah the blue V hot dog cart is on my "keep an eye out" list. And I'm torn between Lou Malnati's and Ord Pizzeria, I looked at pictures of their pizza online and it looks pretty damn good. My neighbor told me to go to Superdawg drive in for a hotdog but idk if I'm gonna go all the way up there, I might just hit up a street cart if it's more convenient.
My other neighbor (born and raised Chicagoan) gave me a pretty comprehensive list of things to do and places to eat.
Gene and Jude's - for hotdogs
Portillo's - get
the "combo" which is apparently a beef/italian sausage sandwich on a hoagie roll that looks pretty good, and apparently it's a local favorite.
And if I have a classier tastes "Girl and the Goat" yes that is the actual name lol.
As far as things to do he highly recommended the Chicago Architecture River Cruise, which for 33 bucks seems very reasonable so I'm probably gonna do this one. Not to mention the Sears Tower but only if there's no fog, otherwise I'm wasting my time. And according to him when he was growing up there (70's/80'sish) authentic Chicago style pizza was a thin crust made with cornmeal, so I'm gonna keep an eye out for that.
And if I have more time left over walking along the lakefront trail sounds pretty cool, along with the Museum of Science and Industry which is right up my alley.