It’s All in the NameBoystown was an ideal stop on our search for the first Gay Travel Guru. With a population of more than 800,000 LGBT residents, Boystown was the first community labeled a “gay village” in North America. With many bars open until 5 am on the weekends, there‘s always a good time somewhere to be found in Boystown. 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 when we arrived, but everybody was friendly and quick to approach us and ask why we were there. As the evening went on, more people arrived and the liquor started flowing. We also enjoyed Roscoe’s music selections, including a mash-up featuring Lady Gaga‘s “Bad Romance,” spliced with Metallic’s “Enter Sandman.” It was pretty cool! And, we left with some great Guru applications.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. We didn’t have to travel too far for the second Boystown Guru launch party. Sidetrack entertains a generally older crowd. This event was somewhat slower for us, but the potential Gurus we found were VERY impressive. From bloggers and web entrepreneurs, to folks in the hospitality business and bartenders, it was a nice mix. The DJ played videos similar to what we saw at Roscoe‘s, but not the expected Lady Gaga or Britney Spears clips, rather from movie musicals. “Annie,” “The Producers,” and some old-school selections. 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 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 TownAfter 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. The property is close to the high-end shops on North Michigan Avenue- another huge selling point.Getting Caught in Tourist TrapsHonestly, 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. We also 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.