Chicago?
 

I am taking a 5-day vacation to Chicago as a birthday gift to myself.

I arrive the morning of Friday, October 13th and depart on Tuesday, October 17th.

Any suggestions?

I was there for about 24 hours after Rush U one year, and I did an architectural boat tour that was fascinating. The buildings there are really neat, and I'm not usually into that type of thing. If you remember the issue with the Dave Matthews Bus that dumped all the sewage onto a boat, it was actually from that tour. Obviously, it wasn't on my day, hahaha.

You could also take a trip to Evanston, I think they're on the subway.

I do believe the el goes to Evanston. I may have an opportunity to head out that way Monday morning so I'm definitely thinking about it.