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Gay Travel

Is There a Guru in Boystown? Arrives In Chicago

Travel by Jon Fairbanks, (From GayCalgary® Magazine, June 2010, page 15)
Gay Travel: Is There a Guru in Boystown? Arrives In Chicago
Gay Travel: Is There a Guru in Boystown? Arrives In Chicago
Gay Travel: Is There a Guru in Boystown? Arrives In Chicago
It’s All in the Name
It may seem too good to be true, but yes is looking to hire someone to travel North America for six months, all expenses paid plus $30,000.  The job?  You have to blog, upload photos and videos and share your experiences with our site visitors.  To help spread the word, we hosted launch parties in San Diego and New York City… next up …the queer capital of the Midwest, Chicago.
Boystown was the ideal third stop on our search for the first Gay Travel Guru.  With a population of more than 800 thousand LGBT residents, Boystown was the first community labeled a “gay village” in North America.  With many bars here open until 5 am on the weekends in Boystown, there’s always a good time to be found.  During the day, my travel buddy Tommy and I enjoyed scoping out the numerous boutiques, restaurants and historic architecture that line this gayborhood.
Both of our flights were delayed because of bad weather and we hit rush hour traffic getting into the city, but we made it in time to host our first launch party at Roscoe’s ( on North Halsted on Thursday.  There was a small crowd there at first, but the big difference from all of the other cities we’ve visited was that everybody was friendly and quick to approach us and ask why we were there.  As the evening went on, more people showed up and more liquor started flowing from the bar.  By the end of the evening, we had a nice selection of Guru applicants.  From the bar area where we were stationed, patrons migrated to the dance floor.  Roscoe’s plays music videos but ones you wouldn’t expect, like a mash-up featuring Lady Gaga‘s “Bad Romance,” spliced with Metallic’s “Enter Sandman.”  It was pretty cool! 
Famished from a hard night at “work,” we headed across the street to The Pie Hole (  For just a couple of bucks, you can get a huge slice of fresh-made pizza.  We didn’t happen to be drunk, but it was great late night food anyway.  The eatery boasts “contemporary pizza” and “stunning views of the 7-11 parking lot.”  I’m not sure what “contemporary pizza” is, but the view of the store was … err … breathtaking. 
For our second Guru launch event, we didn’t have to travel too far.  Sidetrack ( entertains a generally older crowd.  The potential Gurus we found here were VERY impressive.  From bloggers and web entrepreneurs, to folks in the hospitality business and bartenders, it was a nice mix.  If you like show tunes or comedy shows, this is the place for you.  The venue hosts weekly events for every taste and interest.  The DJ played videos like at Roscoe’s, but not the expected Lady Gaga or Britney Spears clips, rather from movie musicals.  Patrons we treated to numbers from “Dreamgirls,” “The Producers,” and a bunch of older stuff.  The bartenders told me that the regulars love it.  I know that’s true because they were reciting lines in unison as the videos were playing.  My favorite clip though was the SNL sketch with Betty White talking about her “muffin” on the mock public radio station.  A new classic!  Wonder how long it will take the fellas to memorize it. 
R&R Across Town
After a night of meeting hotties in Boystown, we trekked downtown to the Magnificent Mile, where we stayed at the Marriott Downtown (  The staff was friendly and quick to accommodate us.  The three room suite was the perfect place to retire and catch a glimpse of the amazing skyline.  Another huge selling point, the property is in close proximity to the high-end shops on North Michigan.
Getting Caught in Tourist Traps
Honestly, sightseeing is not my favorite pastime.  Fighting crowds and paying huge admission fees is not fun for me.  But there were a few key destinations we had to check out while in town.  Our first stop was the Willis Tower (aka Sears Tower).  Reaching 108 stories, it’s the tallest building in the United States.  Inside you’ll find shops, restaurants and offices.  If you plan on going to the top, be prepared to wait.  The line can get pretty long.   
Just walking around, we stumbled upon Millennium Park.  The 24-acre park is indeed a haven for school groups and out of towners.  But the Frank Gehry-designed Jay Pritzker Pavilion, interactive Crown Fountain and other structures are irresistible. 
Bad weather delayed our trip into Chicago, luckily the sun arrived just as we did!  And the boys AND girls that make Boystown a must-see destination, did not disappoint.  
For more information on gay-friendly destinations across the world or to apply to become the first-ever Gay Travel Guru, go to 


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