A bit of personal philosophy: cities, like people have personalities. Personalities are shaped by experience and the influences afforded them. Generally, people gravitate to a living experience that feels most comfortable. I love Philly, but, I could “live” in Chicago too. He’s a big brawny hunk of a town: unpretentious, real and damn sexy!

Back in the last century, my very first “grown-up airplane” trip was to Chicago. It was my first solo business trip and my Pierre Cardin suit with YSL shirt and tie combo was “all that and a bag of chips”! Never left my heart in SFO, but a piece of it is still in CHI! It always will be. Funny how that just is.

Like Philadelphia, Chicago is honest and genuine everywhere. Some other famous and wonderful cities like New York, Paris, and Rome can actually become a distraction in themselves, whereas Chicago, Illinois is simple, direct and proud of it. Must be that mid-western/no-nonsense/carnivore attitude with a bit of “I really don’t give a shit” thrown in. Philly and Chicago: the “what you see is what you get” vibe is very similar. We can both be a little rough around the edges but are darn nice folks.

Chicago is the third largest city in the US after New York and LA. I am not really sure why it is known as “The Second City”, but let’s just not question that. Chicago has areas that are much more “big city” than anything we have here in Philly. Remember that while we are in an area with so much going on, Chicago is a “hub” for most of the country. Many trains, planes and automobile pass through Chicago on a daily basis. That may or may not be best but, the result is that Chicago has a tremendous amount to offer the typical Gay visitor: all sorts of hotels the restaurants with romantic Midwestern histories, some lovely parks, beautiful fountains, stunning architecture “The Magnificent Mile” and a BEACH! Philly doesn’t have a beach. Imagine if the Delaware River were a “Great Lake”, (In this case Lake Michigan, which is for all practical purposes an ocean). The “Lake” has salty water, tides, the whole bit.  CHI-Town capitalizes on their “Beach Front”. As a comparison, Penn’s Landing and Philly’s River front development could be much better in my opinion. Lots of great spaces underutilized. Lost revenue upsets me.

I have read that the reason Chicago is called the “Windy City” is because of the winds off Lake Michigan. I also read that the lake keeps the city cooler in summer and warmer in winter. While no expert on Chicago weather, I can only say that I have never noticed any great winds blowing, it can get awfully hot and humid in summer and I have not experienced many places colder in winter. Once my nostrils really did freeze shut a bit on a cold winter Chicagoland evening. Crazy experience and a very hot night.

In summer, the beach is very much a part of the scene: rollerblading, volleyball, jogging, ray soaking and people watching right in the middle of the urban setting. The entire 28 mile lakefront shoreline is man-made and the Chicago Lifeguard Service is the largest in the nation. It is also the cleanest urban waterfront in the US and second only to Stockholm in the world. Very impressive.

Hollywood Beach is the Gay Beach. It is also known as Kathy Osterman Beach. If you don’t know about this fantastic woman, find out about her contributions to get her into the Chicago Gay and Lesbian Hall of Fame. The amazing and fantastic thing to me is the existence of a Gay Beach in the heart of any city but Chicago offers it. More remote than a more heavily trafficked Oak Street Beach (just off The Magnificent Mile) Hollywood Beach will have everything you are looking for as long as April to October. June to late August is more like it but I just wish Love Park had a beach!

In Chicago, center city is known as “The Loop” although no one is completely sure why. The Chicago River flows through the middle of the city which comes in very handy for tourist trade boat trips and dyeing green for St. Patrick’s Day.

The Magnificent Mile is considered one of the ten best shopping streets in the world and is pretty much true to its name. “Magnificent” Most of the “show” hotels, restaurants and over priced stores are located on Michigan Avenue as is the one time “tallest building in the world” The Sears (now Willis) Tower and Water Tower Place which survived the Great Chicago Fire. It is interesting to see, a sort of mid-city sculpture as well as a monument to never giving up and survival.

Chicago is the “first city ever to be recognized with a Gay Village”. This was in the eighties and during that time period, Chicago was a Central Gay Mecca. Today, there are officially two “Gayborhoods” in the city. Lakeview East, AKA “Boystown” is pretty self explanatory. Andersonville is nearby and is more eclectic and less steeped in testosterone. Although both sections are not in The Loop, public transportation is very good. Not that long ago, fellows like me hit a new town without internet or a fraction of the information afforded men today and  managed to find the action. Gay/Straight/In-Between. Gay friendly Chicago has plenty of places for grabbing a drink with your peeps or arranging “temporary close friendships”. I frankly have found the company just fine in “The Loop” although “Boystown” is fun as well. Maybe I just like the name.

For the jocks: Sox, Bulls, Cubs and Bears, Oh My! I have seen a lot of great theater in Chicago as well as one of a kind concerts and special events. Museums are everywhere and the Chicago Art Institute is superb. Just watching the Sox at Wrigley Field is like watching a ball game, a history lesson and a visit to a museum all in one. Awesome!

For those seeking the finest beef on the planet, The Chicago Stockyards are legendary and if the “Steak House” did not originate here, it certainly was perfected here. Pizza? Seriously? The CHI-Guys are very humorless about their pizza. I prefer a thin crisp, crust to “deep dish” but certainly adapt when in town. They would simply dismiss me as a “Know nothing from the East Coast” anyway. Chicago has a huge ego.

The Bottom Line: I would personally welcome a two/three night holiday in Chicago at anytime of the year. Air from PHL is plentiful/direct and if examined, can be had for a very good price. Tremendous variety in food, lodging and even Gayborhoods is available. What more could you really ask for? They even have a fucking BEACH! We don’t have a beach.