A Whirlwind of Fun Awaits in Chicago

Chicago offers all of the excitement of a bustling American city with unique neighborhoods, great art and culture and nightlife, a vibrant LGBT and leather community, and a big Midwestern heart.

The Windy City is historic and legendary in its own right. Chicago became a city in 1837. Historically, Chicago might be best known as the home of 1920s mob boss Al Capone; for being the founding city of social work with Hull House, established by Jane Addams and Ellen Gates Starr to help the needy with food, education, employment; and being the starting point of Route 66 that heads west to California.

Today, Chicago, which sprawls 237 square miles into its surrounding suburbs, is known for being President Barack Obama's hometown and is on the forefront of marriage equality as Mayor Rahm Emanuel and former mayor Richard M. Daley support the move for same-sex marriage under way in the Illinois Legislature.

Beyond politics, Chicagoland, another one of its more than 20 nicknames, is known for its architecture, deep dish pizza and hot dogs, shopping on the Magnificent Mile, hanging out in Millennium Park, and its professional sports teams, including the Cubs, the White Sox, the Bears, the Bulls, and more.

Then there are Chicago's 2.6 million residents who radiate that friendly Midwestern attitude and style.

Nearly 40 million people visit Chicago annually, taking in museums, theaters, and other cultural institutions. It was hard to believe for this San Franciscan, until I experienced it, but Chicago's food scene is nipping closely at the heels of New York and San Francisco's, with thousands of restaurants.

Chicago truly offers something for any visitor. It's no wonder the Windy City was selected as this year's host for the International Gay and Lesbian Travel Association's 30th convention.

"I know Chicago very well," said John Tanzella, executive director of IGLTA. "They have a wonderful gay village called Boystown with lots of great restaurants and cafes and things to do there. The city has tremendous architecture, shopping, dining, culture, and arts. There's so much for folks to see and do there."

"There's definitely something for everyone here," agreed Christina Wiesmore, co-founder and co-producer of BackLot Bash, the all-women party event that takes place during Chicago Pride. "That's what makes it special."

Who's your daddy?

Aside from its LGBT community, Chicago also has a large leather community. The International Mr. Leather competition and American Brotherhood Weekend both call the Windy City home.

"We have a really solid leather community," said Dean Ogren, a 55-year-old gay man who is the owner and executive producer of ABW.

The city's leather community is unique in the fact that it has a leather bed and breakfast, the Ashland Arms Guest House, and the Leather Archives and Museum.

The leather neighborhood, Eddgewater, borders Andersonville, the lesbihood, in the northern part of Chicago. Ashland Arms Guest House resides on the top floor of an apartment building over 64 Ten Leather Shop, and leather bars Jackhammer and Touche. The leather archive is located about 12 blocks from the guesthouse.

In 2008, inspired by their own B&B experiences traveling around the world, Eric Kugelman, 48, and Michael Syrjanen, 66, who have been together for 16 years, decided to open the BDSM guest house. They also own the 64 Ten Leather Shop downstairs. Syrjanen, a designer, created an exhibition of original kink artwork throughout the guesthouse and designed the five themed rooms, such as the Bunk Room, that overlooks the district's police station. The B&B also sports a shared shower, cuffs and swings, a kitchen, and snacks, among other amenities. Kugelman runs the day-to-day operations of the immaculate, chic and kinky B&B.

The guesthouse is already booked for IML, which takes place over Memorial Day weekend.

Dykes and transgender individuals looking for a play party during IML will enjoy going to Vespertine, an all-women and transgender-friendly play party, on May 26.

Women's community

"There's a lot more things going on for women now than there used to be," said Amy Bloom, a lesbian native Chicagoan who owns Amy Bloom Inc., an event planning company.

Bloom, 40, is very active in Chicago's lesbian community co-organizing socials, such as the springtime Chicago Curve Annual Sunday Social (http://www.chicagocurve.com). The event, happening April 7, attracts more than 100 women for an afternoon of food, drinks and live music.

Chicago has one lesbian bar, Parlour, and three other bars that are popular among lesbians: Joie de Vine, T's Bar and Restaurant, and Rosco's, which hosts a ladies night on Thursdays.

This year's BackLot Bash, the all-women's weekend party, is celebrating its 10th anniversary.

"We always knew we had a busy, vibrant Chicago LGBT community," said Amie Klujian, 44-year-old Chicago native, who co-founded and co-produces BLB along with Wiesmore, 37.

A decade ago the two lesbian friends simply wanted to "create an event geared toward women," said Klujian.

"Honestly, we sometimes forget that we live in an open and accepting community in our city," said Klujian, about queer women who live outside of Chicago in parts of the Midwest that aren't as accepting and open.

It's true, my girlfriend and I were surprised that no matter where we went in Chicago no one gave us a second look if we were holding hands or sharing each other's food. It felt pleasantly like we were back at home.

Boys, boys, boys

Gay men can be found in Boystown, where a concentration of the gay bars, gay-centric shops and the Center on Halsted, Chicago's LGBT community center, is located.

Boystown is also the home of Steamworks Chicago, the men's gym and sauna, which provides one of the few alcohol- and drug-free spaces for gay men to hang out. It's operated by the same folks who run the bathhouse in Berkeley.

"It's a great community space to hang out," said Nirmalpal Sachtev, general manager of Steamworks Chicago. Sachtev, 39, a San Francisco Bay Area transplant, said that the Windy City's LGBT community is "blossoming."

Once the snow melts after the harsh winters, Chicagoans, including the LGBT community, come out to play.

"It's such a beautiful city in the summer," said Michael Snell, who owns http://www.BestGayChicago.com with his business and life partner Derrick Sorles. "[It's] such a lively city [with] so much going on [with] the nightlife and the events. On any given night there is always something going on."

The unofficial gay beach, Hollywood Beach, often attracts upward of 600 sunbathers and volleyball players, said Snell.

Lesbian locals pointed out that Chicago has the largest women's softball league in the nation.

Out on the town

During the day my girlfriend and I zipped around on the city's public transportation with our unlimited seven-day pass that we got as soon as we arrived at O'Hare International Airport.

During the day we toured some of the neighborhoods, such as Andersonville and Lincoln Park, and touristy spots such as Navy Pier. Armed with our Chicago CityPass, the best way to see the main attractions without the full price or lines, we hit the Art Institute of Chicago, the Field Museum, and Shedd Aquarium.

We checked out the nightlife, mostly at gay bars in Andersonville, Boystown, and downtown as well as local hot spots, such as the Untitled Speakeasy. At the only gay bar downtown, the Downtown Bar and Lounge, we enjoyed a very competitive and lively karaoke over beer.

One of the highlights of our nights out were cocktails at the Signature Room at the John Hancock Building where we overlooked city lights that lit up the town for miles.

Unfortunately, we didn't get to take the architecture boat tour, which everyone we spoke with said was a must do, or check out Chicago's theater district. It wasn't until we arrived that we learned that the Windy City has a thriving theater scene and is the testing ground for many Broadway shows before they head to the Big Apple.

Sleeping around town

Chicago is so vast it's best to find a hotel either near where you believe you will spend most of your time or a central location, like downtown, where the neighborhoods are easily accessible.

Boystown currently offers three nice options with sister hotels City Suites, the Majestic, and the Willows. City Suites is the closest to the action at the south end of Boystown. It's not quite as nice as the others. What it offers is proximity to Boystown, a block away, and the Red Line, which runs right past the hotel.

The Majestic, where we stayed, is the other closer option to Boystown. A boutique hotel located about three blocks from N. Halstead, the main strip of Boystown, it is charming, the nightlife is easily accessible, and it offers a quiet retreat.

The Willows is a beautifully appointed hotel and popular among women, but the farthest from Boystown.

We spent the rest of our time downtown where we stayed at the newly built Radisson Blu Aqua Hotel, Hyatt Regency Chicago, and the historic Drake Hotel.

The Radisson is impressive. Designed by architect Jeanne Gang of Studio Gang Architects, the hotel is beautiful inside and out and overlooks Millennium Park and Navy Pier (as our room did) on one side and the cityscape on the other side of the building. The Radisson Blu Aqua is the first of the European style Radisson hotels to be built in America.

Around the corner is the Hyatt Regency Chicago, which is the official host hotel for both the IGLTA conference and IML.

There is something to say about historic style at the Drake. Our room came with two full bathrooms, which for women and stylish men is sometimes important. The room was also spacious and elegant and overlooked Lake Michigan. On the bottom floor of the hotel was Coq d'Or, the first bar in the city to open its doors after Prohibition.

The Drake isn't as close to the theater district, restaurant row and other attractions as the Hyatt and the Radisson, but it is near high-end shopping and the Signature Room.

The food

Once my girlfriend knew we were heading to Chicago she couldn't stop talking about getting her hands on a classic Chicago hot dog. She grew up in a suburb of Chicago and misses some of the foods from her childhood. Surprisingly, it was a tough task to accomplish with Chicago's vast and rapidly growing food scene. But on our final night, we dug into the city's classic deep dish pizza at Lou Malnati's Pizzeria and for lunch on the way out of town enjoyed a hot dog with all of the fixings at Portillo's Hot Dogs.

Foodies to the bone, we were dazzled by Chicago's booming restaurant scene. Chicagoans are leaving behind their "meat and potatoes" plates, opting for a diverse array of delectable dishes from around the world and of course giving global fare a Windy City twist, such as at Zed451, a Brazilian-style steakhouse.

Zed451 is an experience not to miss. If you know you are heading to Chicago, make reservations as this downtown restaurant is a unique three-hour dining experience that is popular among locals and visitors alike.

This is an experience to be savored and enjoyed, so I advise going hungry, but pace yourself. It is easy to fill up fast on the wide variety of appetizers and soups and salads at the buffet in the center of the restaurant. Appreciate the food and the moment, and dine slowly to enjoy the array of offerings that will be brought to your table.

Harvest fresh food has hit Chicago's restaurants. Nearly every restaurant is boasting fresh and flavorful in season produce seen more often on the restaurant tables in the Pacific Northwest and in New York City.

It s a part of Chicago's health kick that the city s been getting on within the past year. Three healthy eating restaurants have popped up in Boystown alone recently. For healthy dining downtown, Roti Mediterranean Grill offers a quick bite to eat, but if you've got some time while shopping or taking in the sights check out La Madia for artisan pizzas and light Italian dining or Filini at the Radisson Blu Aqua Hotel.

Hanging out in Boystown we enjoyed dinner at the Kit Kat Lounge and Supper Club, a toned down version of AsiaSF, and Bountiful Eatery.

For outdoor entertainment, Edward Disiger, 44, who owns Kit Kat with his business and life partner of 15 years Ramesh Ariyanayakam, 46, shows screenings of movie classics on the side of the restaurant.

At night, the lounge is usually the first stop of the evening for many guests before heading out to the Boystown bars and clubs, said Disiger.

It was our first stop when we arrived in Boystown before checking out the nightlife at Roscoe's for Sin, the gay bar's ladies night; Sidetracks, a popular nightclub; and catching a nightcap at the Closet. Bars tend to close between 2 and 4 a.m. in Chicago, to our delight.

We definitely needed a healthily lunch the next afternoon. We found it at Bountiful Eatery, where Ed O'Brien served us up tasty gluten-free plates of quinoa salad that had a kick to it and a turkey wrap with a side of salad.

Inspired by his own dietary needs, O'Brien, a 53-year old Chicago-born and raised gay man trained at the Institute of Culinary Education in New York, opened the restaurant nearly nine months ago. It has been a runaway hit, he said, as a lunchtime crowd began to filter into the sun-filled restaurant.

O'Brien said he's pleased about the changes Chicago's food scene has undergone since he left. He returned six years ago. Now there are "all sorts of foods," he said.

We left Bountiful Eatery and strolled through the Boystown, checking out the shops that ranged from high fashion boutiques to kitschy, such as Gaymart Chicago, where you can get things all-gay.

Getting to Chicago

We love Virgin America, which we flew directly from San Francisco International to O'Hare. The flight was comfortable, even with delays, and the staff was friendly. We couldn't have asked for a more pleasant flight.

Check ebar.com for a quick guide to Chicago.