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Gay Travel - Gay Couple Visits Boystown Chicago

After a great time in New York we hit Chicago running. Actually wrong choice of words we hit Chicago exhausted after having such a good time in New York with friends. I was also still in shock and pain from having to sit in the last row of the plane where the seats do not go back. That’s one of the drawbacks when you try to be spontaneous, no good seats.. We were lucky we had 2 days to recuperate before a family wedding and Aaron’s first Shore wedding.


We were lucky to be staying at a good friends apartment on the lake in Lincoln Park, which is about a mile from the city center. It was a huge place and if we wanted to see my friend we would have to go looking for him or try calling him. Privacy was not an issue. It was like having our own home and for the week we were there Aaron was able to get an idea of what it might be like to live there if we ever decided to move back to the States. I have said before that I grew up in Chicago.


Gay couple Aaron and Mike in Chicago

The weather was cold which was fine with us, as we could spend a lot of time inside lounging around doing nothing except catching up on our sleep. There were only 2 days when the weather was actually nice enough for me to show Aaron around. Just like New York, the city was crowded with people for the holidays. Most of the better restaurants were already filled with reservations but Aaron did get a chance to try some of the foods Chicago is famous for.


The foods ranged from deep dish pizza, burgers, hotdogs, italian beef, popcorn, ( I know strange,) food from the Bagel which has been around for 50 years and is an old time Jewish Deli and desserts that I only dream of in Ireland. Just one of the foods Ireland does not do well. Actually Ireland is not a place you would ever visit for the food, (it is still a great place to go.) unless you were coming off a 60 day fast. It’s funny, where New York is famous for pizza by the slice, Chicago is known for their burgers and dogs which I did not realize how much I missed until our visit and I was scarfing down one or two a day.


On the days it was warm enough to walk I tried to show Aaron Gay Chicago as I remembered it, although it has changed quite a bit. Years ago a great many of the gays lived in an area going north from Diversey Street to Addison or a bit farther north and from Hasted to Broadway. This neighborhood was about 2 miles from the center of the city.


This has changed over the years as it does in may of the big cities when neighborhoods are gentrified and many of the younger people are priced out. Now many of the gays have moved farther north and west in the city. In the summer I remember the boulders on the lake at Belmont Avenue were a big cruising spot. It was also hard for him to get a good idea of just how many gays live in the area as it was so cold that every person was completely dressed in winter gear. Not even the best gaydar would have worked. I was a little disappointed as we have talked about the gay scene in Chicago and I wanted Aaron to get a good idea of what it was like.


Aaron and Mike in Boystown Chicago

My friend who we were staying with on the lake was a block from Clark Street which runs North South through the city, Many days we did our errands on this street which happens to run through Boys Town. One day we needed a few things and stopped at Target to get them and I decided to try on some sweats. I asked one of the workers if they had a dressing room so I could try them on. It seemed very odd but she pointed to a square in the middle of the store. It was basically a free standing dressing room with walls beginning about 18 inches off the floor and going about 7 feet high. Well it must have been my lucky day. Aaron was finally feeling rested and a bit frisky and I barely had my pants off when...... I don't think I have to tell you more . So if any of you get a bit horny, are into public and in Chicago, you know where to go for a little playtime.


Most of the gay bars are located on Halsted Street between 2600 North and 3600 North and the streets Belmont and Addison which intersect Halsted. You can pretty much walk the whole area. Also located there is The Chicago Steamworks a famous Chicago Institution for gay sex which has been around since I believe 1990. I was lucky enough to visit it about 5 years ago and loved it so much I probably spent a few days there. I was single at the time.


Due to our family wedding we really didn't get a chance to see the bar scene in full swing. We did try a few bars on Halsted. Unfortunately we did not get to try the 3 bars that Esquire magazine said were some of the best in the country because they were so far north. Esquire named Farraguts, Carol’s Pub and Big Chicks adding that they were all LGBTQI friendly.


The first place we tried Sidetracks on Halsted is basically a huge club with great dancing, video screens, a few floors and pretty strong drinks. As with most of the bars in the city everyone is pretty friendly. If you're looking for a good time with friends this would be our pick. Next we tried Roscoe’s another bar in the same area. Much smaller than Sidetracks but has the added attraction of pool tables, an outdoor patio and drag shows. Our third and final bar was The Cell Block, Chicago’s leather bar. it is the place to go for ”puppies and leather/levi daddies.” There were two main rooms, the front for dancing, pool and what not and a back room that got kinkier the farther back you went, also a patio. On a crowded night this would have been our favorite but Aaron and I always seem to like it a little sweaty and raunchy for lack of a better terms. If you are looking for cruising and sex Cell Block would be the place to go on weekends. It is pretty tame during the week and the back room is only open on weekends


In addition, to just seeing gay Chicago I tried very hard to show him around the city. Despite the cold we managed to see a lot of it. We walked along the Chicago river. Went to Millennial park which is behind the Art Institute a fantastic museum. Michigan Avenue where most of the good shopping is found. The Loop, where many business are located. We walked all along and through Lincoln Park. which runs along the lake.The South Loop which has become a new residential neighborhood. Now that I think about it we really did much more than I originally thought,


All in all Aaron thought the Chicago gay scene lived up to what I told him about it, despite my never really being a huge part of it and not living in Chicago for 30 years. He hopes we can return sometime when the weather is warmer and not so quiet due to the holidays. I also have a gay nephew who I am counting on to show us more.


Of the three big cities I have lived in, Chicago, New York, and Los Angeles I am surprised to hear myself saying Chicago is the most livable. LA was always my paradise, but it has become very difficult to live there due to the traffic, lack of good public transportation and what I think is a terrible homeless problem and the weather which is really hurting the state. New York which I always loved has simply become too expensive to really enjoy. It does however, have the best public transportation system of any city I have lived in. I would compare Chicago to a cleaner, smaller ,nicer New York, where the people are friendlier. However, there is a crime problem. In any city these day it is just smart to always be aware of your surroundings. You never now what can happen.


Aaron and Mike in Chicago

Hampering our bar and club going in Chicago was the family wedding. Originally we were not planning to go to Chicago, but I would have received hell from my family if they found out we had been in New York and did not attend the wedding. I was pretty excited as Aaron had still not met all my brothers and sisters. It was also the first time the 7 of us, siblings would be together in I don’t know how many years.


I had a great time as I usually do when we are all together and I was glad Aaron felt the same way. In addition to meeting the rest of my siblings he also met many of our relatives. It really made him feel good that everybody seemed to know who he was and made an effort to get to know him. It was still only his second time being with the Shore clan. I love the fact he is finally getting to know everyone and can’t wait till April when we will be in Arizona again visiting.


At the wedding some relatives and I were talking about how diversified, (not sure if that is the right word,) our family has become. I grew up in an upper middle class Jewish family. Today our family is made up of 2 husbands, non Jews, a Mexican, an Afro American, an Israeli and a few more I can’t name off the tip of my tongue. It makes me so happy that today this does not make a difference to anyone. Everyone in our family is so accepting and loving towards one another.

Probably about 70 or so years ago my father’s mother who was a poor uneducated immigrant Jew would not speak to her son or daughter-in-law for about 10 years because he married a non Jew. it took my mother that long to break my grandmother down and she was still barely cordial to my aunt. It really warms my heart to see how far, not only my family has come, but also so many others. I hope the world keeps changing like this and continues to realize we are all just people.

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