Gay-friendly vacations by neighborhood

Tue. October 13, 2015 12:00 AM
by Jay Deratany

True Chicagoans know that neighborhoods are everything.

While we all love this city through and through, we can't help but play favorites among the many unique and diverse neighborhoods Chicago is known for.

And let's be real...Windy City residents tend to identify themselves and one another by the areas where they choose to live and play – the names of the hoods are even sometimes used as adjectives to describe people. "He's so Lincoln Park" or "She's definitely a Pilsen type" are surely things you've heard before.

With that in mind, here's a list of gay-friendly vacation destinations that are the perfect fit for lovers of a few of Chicago's best-loved neighborhoods.

If You Love Boystown, You'll Dig New Orleans

Of course we had to start with Chicago's quintessential gayborhood, Boystown. However you feel about this party hearty pocket of town, it can't be denied that it's pretty fabulous. With its huge selection of amazing restaurants, boutiques and happening watering holes, it always draws a crowd that's up for a good time.

Many of the same things can be said about The Big Easy. No matter when you go, this iconic city is overflowing with things to do. And not only are New Orleans visitors always ready for fun, but the locals are known for being exceedingly friendly, tolerant and laidback as well, which makes for a welcoming atmosphere for all.

Be sure to check out what's known as "Lower Bourbon," the section of the world-famous Bourbon Street, which has the city's highest concentration of gay bars and clubs. But if you want to get a little more of a local flavor, hit up the live music joints on Frenchmen Street or the burgeoning super hip neighborhood called The Bywater.

If You Love Lincoln Park & Lakeview, You'll Dig Dallas

These North Side neighborhoods are widely considered home to Chicago's yuppie set and are most popular with young, wealthy singles who often remain there once they start families. The streets are lined with beautiful old homes, beautiful people and a wide selection of high-end businesses that cater to their upscale residents.

While you may have your assumptions about what Texas is and isn't, you probably don't know that the thoroughly modern Dallas has the 6th highest LGBT population in the country and is even home to the largest gay church in the world, The Cathedral of Hope. And like Chicago, this Texas town has 2 thriving LGBT neighborhoods. Check out Oak Lawn to see Dallas's epicenter of LGBT culture and visit The Bishop Arts District for a gayborhood that's a little quieter and artsy.

If You Love Andersonville, You'll Dig Saugatuck-Douglas

Andersonville is generally considered Boystown's chill, quaint cousin to the north. With an equally thriving LGBT community, this hood is all about the artsy, independent businesses. This gives the area a distinctly small town feel, which is one of the many things that Andersonville fans love so much about the place.

If A-Ville is your scene, then you'll feel right at home in Southwest Michigan's sister towns of Saugatuck and Douglas. Just 2 and a half hours' drive from The Loop, this area has long been a popular vacation destination for well-to-do Chicagoans. The result is a place that retains an adorable small-town vibe while also offering sophisticated urban visitors a wealth of fine dining, art galleries and events.

Saugatuck-Douglas also has a long LGBT history and is home to a great many gay-owned and gay-friendly businesses. During the summer, get your lounge on at one of the many pristine Lake Michigan beaches. And throughout the year, you can visit the area's independent wineries, breweries and art galleries.

If You Love the Gold Coast & Old Town You'll Dig Palm Springs

These two-centrally located areas have as much old money as they do stunning lake views. You Chicago high-rollers love these neighborhoods for their designer shops, urban mansions and fancy restaurants. And who could blame you? The Gold Coast and Old Town are home to some of the most beautiful architecture and picturesque scenes in the city.

But when it's time to shake things up, you'll want to head to Palm Springs, a well-established playground for the well-heeled LGBT set. And with its year-round perfect weather, laidback atmosphere and jaw-droppingly beautiful homes, it's no surprise that this desert oasis is what it is today because of the prominent gay Hollywood crowd of the mid-twentieth century.

If You Love Logan Square & Wicker Park, You'll Dig Asheville

If your taste in neighborhoods leans a little more hipster, you're probably often found hanging out in Logan Square and Wicker Park. These areas are all about cool little coffee shops, hip restaurants, craft cocktails and live music.

For those who call these west-side hoods home, Asheville, North Carolina is an ideal vacation destination. This small, eclectic city is frequently found on "Happiest Cities" and, "Most Beautiful Places in America" lists and is known for its gorgeous architecture and happening music scene.

The hippy vibe is strong here due to the city's high concentration of street performers, art galleries and artisan dining options. And with a higher-than-average number of gay bars and its own LGBT Pride Festival, you can be sure that Asheville is welcoming of visitors of all sexual orientations.

Truth be told, regardless of which Chicago neighborhood you identify with, all of these fantastic vacation destinations should be added to your travel bucket list. You just might find a favorite new escape that you never expected.

About the Author: Jay Deratany is a travel blogger and whose other titles include attorney, LGBT rights activist, screenwriter and film producer. He recently added "hotelier" to that list when he opened the The Kirby, a Saugatuck bed and breakfast that's a lot more modern and luxurious than your average B&B. The hotel also include's J. Paul's, an upscale wine bar and restaurant. For more info, visit