Good times in The Windy City

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Chicago is the largest American cultural center not located on the East or West coast. 

It does, however, sit next to a fairly large body of water. Lake Michigan provides heavy-duty winds and a stark visual contrast to Chicago’s spectacular downtown. Besides deep dish pizza, architecture and the Chicago dog, the great city on the lake also has a well developed GLBT culture. The multiple quick and cheap flights from Nashville International to either Midway or O’Hare make Chicago a great weekend getaway for Music City’s gay set.

I have been to Chicago several times. Most often on business or to attend a convention of some sort. This trip was my first visit to the city for pure leisure since I became an adult. My partner Jason and I decided to stay at a downtown hotel, The Amalfi. It was a decision we would not regret. 

The Amalfi is a smart boutique hotel that prides itself on exceptional service. Though the service seemed no greater than any other luxury hotel, the room was spacious, clean and well designed. The bed was so comfortable that Jason, who normally has trouble sleeping outside of our bed, slept like a baby every night. 

There are a couple of things that set the Amalfi apart from its downtown competitors. First, the hotel offers free WiFi throughout the building and the signal was just as strong in my sixth-floor room as it was in the street-level lobby. The Amalfi also offers a free continental breakfast buffet on each floor. You don’t have to worry about dragging yourself down to the first floor every morning, just throw on your slippers and make a quick dash to the elevator foyer. The Amalfi’s central location is just blocks from the Magnificent Mile and close to major public transportation.

Chicago’s gay scene is deep and diverse. There is a bar here for everyone. If you are staying at the Amalfi, the famous Gentry of Chicago is just a block a way. 

Gentry is a fun, laid back place with various forms of entertainment that anyone can enjoy. For the greatest concentration of gays, you need to catch the Red Line train up to Boy’s Town. You’ll know you on the right street when you see the rainbow themed street lamps. 

One of Boy’s Town’s most popular spots is the dance club, Hydrate. Hydrate is always packed to the gills with hot boys, sans shirts, gyrating and drinking. If flashing lights, dancing guys, and top flight DJs are your scene, then Hydrate is your place. 

The Cellblock in Boys Town is a world famous Leather Bar; just one of many to be found in the Chicagoland area. 

Those of you who enjoy watching boys dance and strip as much as legally possible will probably want to visit the Horseshoe Lounge. There is a lot more to Boys Town than that however; just walk up-and-down Halsted Street and you are bound to find the perfect watering hole. After a night of drinking, dancing and flirting you’ll want to visit Nookies. This late night café has an extensive menu and everything on it is good.

There is, of course, more to do in Chicago at night than clubbing. The city has several world-renowned arts organizations. During this last visit, we took in an amazing production of Giulio Cesare at the Lyric Opera. Opera might not be for everyone, but the Lyric’s epic productions will convert even the most uncultured skeptic. Giulio Cesare featured three singers of my favorite vocal type, the counter-tenor. While the other two were more than adequate, it was Gerald Thompson in the unfortunately small role of Nirenus who wowed me with his sweet voice and versatile acting ability. 

Besides the opera, Chicago also has a bevy of theatrical productions to choose from. Most of them rotate in and out but both the Blue Man Group and Wicked are enjoying long runs. Renowned local performance companies Steppenwolf Theatre and The Second City round out your entertainment options.

After our night at the opera, Jason and some friends of ours stumbled upon an amazing new late-night eatery. Quartino, on the corner of State and Ontario, is a tapas-style wine bar. I am sure the wine is good, but I was too involved with the food to order any. If you visit Chicago you must stop by Quartino and try the veal meatball sliders. You can thank me later. 

If you are determined to try some authentic deep dish pizza, you can’t go wrong with Lou Malnati’s. This Chicago institution has several locations and can even ship your favorite deep dish pie to your home in between visits.

That’s my rundown of the Windy City. It is far from comprehensive but should give you some ideas of where to eat and play. 

Chicago is a great city to visit during both during the in and off seasons. As long as you can avoid a significant snow storm, you will have plenty to keep you occupied all day and night.