I will be in Chicago 10/20 - 10/24 for Northwestern University's homecoming weekend, staying at the Sheraton and W Lakeshore.^
Let's see... since my April 2005 post, there have been a couple additions to the gay circuit. However, since I spend most of my time in Honolulu now, I do not guarantee that these places are still what I remember them to be:
Minibar (Sun - Fri close at 2 am, Sat close at 3 am) - Chicago's only smoke-free bar for the gays. Bartendars are good to look at (ok at least one named Luke, not sure if he's still there), but may not have the best degree is mixology. However, they do have infused vodkas that you can't anywhere else in Boystown. Atmospher-wise, think W Hotelesque-style bar... comes with the same attitude free of charge.

Minibar is where Felt used to be. Web site is
Minibar.
There have been 2 new additions to the Sunday night festivities since my post in April 2005. Both of these are downtown:
Cabaret (open 'til 4am). The last time I went, it was gay on Sunday evening. We'd used to go around midnight or so. However, can't seem to find any info about Sunday nights on their
web site.
Wet (open 'til 4am). Same with Cabaret... can't find any info on their
web site.
One place I forgot to mention previously is Kit Kat Lounge. It's a supper club and martini bar with nightly shows of female impersonators. Sunday nights are half-off all of their 50+ martinis. For fun, there is a psychic that will do your tarot card reading for $10. Web site is
Kit Kat Lounge.
Monday nights now include Chances. It happens only once a month, on the 3rd Monday of each month. Catered to the more alternative, artistic, uber intellectual gays and lesbians. My friends tell me it's saturating and becoming more mainstream. Web site is
Chances.