Chicago is truly one of the best cities in the USA. Although it is a huge city, Chicago does not feel overwhelming at all. From a vibrant downtown to quaint neighborhoods, Chicago has a little bit for everyone. The only negative that Chicago has is its miserable winters. The Windy City's winters can be unbearable with wind that cuts right through your body. The other 3 seasons (especially spring and fall), Chicago weather is great.
Chicago is an easy city to get around. With the above-ground trains (called the "L") to the walkable streets, Chicago is a great city for those that like the convenience of a big city. Being on Lake Michigan, Chicago also has a ton of outdoor activities centered on and near the lake. Chicago was designed and planned with beautiful linear parks that front the lake.
One thing nice about gay Chicago is how close everything is to each other. Although there are gay bars spread out throughout a number of the neighborhoods, the center of gay Chicago is Boystown. Halsted Street runs right through the center of Boystown and is the location of many of the popular gay bars. On Halsted Street you will find SideTrack (a great video bar!), Spin (Dance and Cocktails), and Hydrate (Dance). There is also a huge bathhouse in the center of Boystown (Steamworks) right next to all of the gay bars. The one thing that is different about Chicago is the type of guy that goes to Steamworks. In most cities, bathhouses are something everyone goes to....but no one admits (or talks about). In Chicago, Steamworks fills up with the hotties after the bars close....and everyone talks about going there. They come in groups....and hang out together. Going to Steamworks is more like an after-bar hangout for the hot guys (as opposed to a place to get laid).
The one night I went out in Chicago, I met up with my Porn Star friend Scottie Brooks. Since he works as a bartender at Spin, we started there. After a few drinks, we made our way to SideTrack. SideTrack is always packed and the night we went was no exception.
When I visit Chicago, I prefer to stay in Boystown. The hotels in the area are more like neighborhood inns, but it makes a bar night easier when you are staying closeby. There are a ton of gyms in Chicago, but when I stay in Boystown I usually work out at either Bally Total Fitness (not that great....but a lot of the hotels offer free day passes) or Fitness Formula (nice gym in the middle of Halsted Street). There is a new Lakeshore Athletic Club on Broadway that opened recently and I was told this is the new "place to be" in Boystown...but I have not tried it out yet.
Now for the picture at the top of this post. These towers (with the colors of the gay flag) line the street in Boystown. Once you see these towers, you know you have arrived at the center of gay Chicago.
