There are so many places to visit in Chicago, that you'll need to do this style trip a few times, just so you can explore more of the city. This is a fun way to do it, that way you're always trying out new places, and visiting some places you loved when you went before.
I met a friend and we did bottomless mimosas one day. I will warn you, every time I do this in Chicago, it gets really crazy. They pour very well, and for the price it's well worth it. I will warn you that by the time you're on your fifth craft, it sneaks up on you. Or maybe it's not and you don't realize you're at number five.
If you go and it's a little cold, I usually hit up the AMC River East. It's always fun to see a movie and get that large popcorn.
Of course, there are so many different bars and restaurants to hit up, I like to start at a place I've been to and like, and then explore something new after that.
I always have to have Ceasers while I'm there for those amazing margaritas. They come in pitchers, which is the perfect size for me.
Have you been to Chicago? Let me know some spots you like so I can try them out.