Go for a drink on the 95th floor of the John Hancock, walk down Michigan Ave (and Oak Street), visit the Art Institute on Michigan, the Symphony on Michigan, the Field Museum, the Adler Planitarium, and the Shed Aquarium. If you have time go to the Lyric Opera, the Museum of Science and Industry, and the Chicago Options Exchange. Lastly don't forget to go to (gay) Halsted Street and make sure ou visit Sidetracks and Berlin.
Do a couple of the tours...river tour and a walking architectural tour are fantastic. There is also a tour from the "el" train which is sorta cool. Chicago Historical Museum and less educational but A LOT of fun - hit the lakefront on the weekends. There is a gay beach - Kathy Osterman Beach - and a straight beach with a beach house bar filled with hot men to stare at...at North Avenue Beach. I wouldn't try tO pick any guys up at North Avenue but there isn't any harm in looking...finally...see if they are playing movies in Grant Park and get ahold of the street/neighborhood festivals. There are several each weekend...hit me up offline if yOu have any specific questions!
If you are in to theatre, there are some good plays coming up. Including the one-man show "the Night Larry Kramer Kissed Me" at Luna Central. Google it. Something different to do than the average Pride week of partying and getting drunk