Portillo's: omg amazing Italian beef sandwich, which I got with both hot and sweet peppers. Juicy, like beef should be, soft bread to soak up all those juices...I wish I'd gotten another one.
Ricobene’s breaded steak sandwich: when I found out I'd be going to Chicago, this sandwich review was the first thing that came to mind.
So yeah, this sandwich is indeed pretty amazing (as was their chicken parm). You should go. But only, you know, if you like meat and carbs at all.
My cousin had recommended the Chicago Architecture Foundation River Cruise, which was really fun and educational! I waited to make sure the weather would be nice before buying tickets at the riverside kiosk about an hour before the first cruise on Saturday.
The tour guide was really knowledgeable and unlike some reviews I had read online, I thought the information was really accessible and interesting. I would not have noticed all the interesting details and thought behind the city's architecture at all otherwise. It does get pretty windy and cold out on the water even when it's sunny out, so bundle up unless it's deep into the summer.
Millennium Park, of course, with The Bean:
The Art Institute of Chicago is right there too, which was a good-sized museum, not overwhelmingly large. Famous stuff they've got: American Gothic, A Sunday Afternoon on the Island of La Grande Jatte, and usually they've got Nighthawks too though it wasn't there when I visited sadly. Also, these gorgeous stained glass windows by Chagall:
Took in a show at the Second City, which is probably a requirement:
Went to this Trapped in a Room with a Zombie with a friend at her suggestion, that was a fabulous time if you like solving puzzles under pressure (I'm an engineer, of course I'm all over that!) With a group of up to 11 other people, you're locked in a room with a (actor playing a) zombie chained to the wall and various puzzles/clues scattered around for how to find the key to get out of the room. Its chain extend by another foot every 5 minutes, and if the zombie touches you, you're dead, so you've got an hour to get out. The success rate is apparently only around 28%, and yet our group managed to succeed!
And lastly, instead of the Skywalk, my friend recommend going up for a drink in the Hancock Tower Lounge for an equally excellent view of the city and approximately the same cost (including the drinks!). There was a bit of a line to get in there, which might've been better if we'd gotten there a bit earlier before all the people wearing tight dresses and shiny suits came out.
Next time I'm in Chicago, I will definitely go back for those beef sandwiches again, set aside more time to wander through the Art Institute, and try to find some of the public art sculptures.