Solo in Gay Chicago – 2TravelDads

Author: , February 17th, 2018

gay Chicago - 2TravelDads

The USA has several cities that are known around the world as being iconic or embodiment of America. We think of New York, San Francisco, Seattle and Chicago. We haven’t all gotten to to each of the cities as a family, but finally I got to do Chicago solo… and I wish I would’ve had the family with me.

Chicago solo travel is a great city adventure. Museums, food, historic buildings and tours, it’s a perfect weekend escape or easy to explore as a business traveler. 2traveldads.comChicago solo is really awesome though and totally easy to do in two or three days; you could even do Chicago solo in one day if you were really in a pinch and wanted to. It’s an easy, walk-able city with unlimited potential and unforgettable sights.

1. Walk the streets of Chicago

Doing Chicago solo is so easy because it’s such a walk-able city. Most of the key sights and museums are all around either the Chicago River or the Magnificent Mile, aka Michigan Ave. Walking the Magnificent Mile will let you see some of Chicago’s incredible architecture, maybe let you do some shopping, grab food, and the get you to any museums you want to visit.

Full Story at 2TravelDads

Illinois Gay Travel Resources

Gay Chicago Keeps Getting Better

Author: , November 5th, 2016

Chicago Gay Tourism

‘Remember to breathe,’ I tell myself, as the helicopter pilot’s voice rings through my ears, my body judders and 1,172 glittering high rise buildings unfold before me. The Chicago Helicopter Experience is shredding my nerves, but it’s also highlighting just how magnificent this 2.7 million-person city truly is.

Grandiose skyscrapers pierce a skyline at once jagged and curiously neat – a result of meticulous urban planning after the Great Chicago Fire of 1871. Behind me, the staggering Lake Michigan disappears into the night like an ocean.

Like the lake, gay Chicago – Obama’s hometown – is huge; the largest in Illinois. The state capital of Springfield – the former hometown of Abraham Lincoln – is a three-hour drive away, and home to just 117,000. The view is exhilarating, expansive, absurd, and in my book, about as glamorously cosmopolitan as America gets.

By Jamie Tabberer – Full Story at Gay Star News

Illinois Gay Travel Resources

City Sundays – Chicago

Author: , July 12th, 2015

City Sundays - Chicago

Hey all,

We’re launching a new weekly series on the blog and our Facebook travel groups – City Sundays. Each week we’ll select a different LGBT friendly city to talk about, and we’ll invite our innkeeper and travel agent/tour operator friends to come talk with us about it as well.

Today, Chicago. We were there in 2002, in late April, and spent almost a perfect week. Though the Windy City can be just that, it’s also beautiful and clean, with lots of metrosexuals (or whatever the heck we’re calling them now)

Have you ever been? What did you do while you were there?

Do you wanna go?

Let’s chat! Join the conversation here:

Gay (Men) Travelers: Gay Travel Club
Lesbian Travelers: Lesbian Travel Club
Transgender Travelers: Transgender Travel Club
Bisexual Travelers: Bi Travel Club
LGBT Families: LGBT Families Travel Club

Check out our Illinois page here:

And our Chicago articles on the blog here:

What’s New in Gay and Chicago

Author: , May 21st, 2015

ChicagoThe stools at Dove’s Luncheonette (1545 N Damen Ave. Tel: 773-645-4060. in Wicker Park are crafted of a shiny, rich brown vinyl and gleam with newness. On a bustling weekday afternoon each one will be flattened by Midwestern butts–which are arguably more voluminous during the winter months. Dee Dee Warwick’s “A Fool for Love” is playing on a record player, not on the vintage Select-O-Matic 100 jukebox hiding in the corner, which works only about half of the time.

Meanwhile, gratuitous wood paneled walls give the whole place a kind of 70s dive bar vibe and provides the requisite cue that we are deep in the heart of hipster country. But the real draw at this newly opened throwback diner from superstar chef Paul Kahan (Big Star, the Publican) is the menu whose Tex-Mex inspired standouts include smoked brisket with avocado, pico de gallo, chicarones and green chile vinaigrette rolled into a large flour tortilla, or chicken fried chicken drenched in chorizo verde gravy and topped with sweat peas and pearl onions. It is joints like this that remind the world why Chicago is everyone’s kind of town.

There is much to be excited about in Chicago these days. Yes, it’s still cold December through March (and sometimes November and April), yes the crime rate is higher than residents would like it to be (although way down overall when measured against previous decades), and yes the Cubs still suck (but does anybody really honestly care?). On the other hand, a spate of enchanting new public parks are slated for 2015 arrival (two of which are profiled below), neighborhoods like the West Loop, Fulton Market, Pilsen, and Logan Square that were quiet a mere decade ago are now chockablock with bars, restaurants, shops, and art galleries, and the city’s queer scene has gotten so big that Boystown on weekend summer nights rivals places like the French Quarter and Ybor City in terms of exuberant revelry.

By Jason A. Heidemann – Full Story at Passport Magazine | Illinois Gay Travel Resources

A Winter Walk Around Chicago

Author: , February 27th, 2015

Chicago - Laura MottaNo matter your tastes, whether you’re into stately neoclassical, ’60s mod, or swooping steel-and-glass, Chicago has an architecture style for you. And if you’re happy to gawk up at all of the above, it’s a feast. Stop into The Rookery, one of the most iconic structures by World Exhibition designers Burnham and Root, for a tour of the lobby ($7), which was given a gold-and-glass update by Frank Lloyd Wright in 1905. For a free glimpse at an architectural marvel, stop into the Chicago Cultural Center.

The space not only offers programs and classes throughout the year, the building’s showpiece is a swoon-worthy Tiffany glass dome — the largest in the world. For more modern trappings, snap photos of the famous “corn cob” towers, more formally known as Marina City, situated right on the Chicago River, then warm up by the fire in the lobby of the nearby Raddison Blu at the Aqua.

The exterior by architect Jeanne Gang, with its irregularly shaped balconies, is a geometric feast for the eye, and the hotel lobby has a coffee bar and a sleek gas fireplace that spans the length of the room. Be sure to pop into the expansive lobby of the Palmer House Hilton, with its brilliantly frescoed ceiling by French artist Louis Pierre Rigal. Have a drink at the bar, but be sure to stop at the Monroe St. entrance for a glimpse at the gilded “peacock door” — another scrolling Tiffany confection that dates back to the days when there was a fine jewelry store in the building.

By Laura Motta – Full Story at Shermans Travel | Illinois Gay Travel Resources

Image by Laura Motta

Traveling with Pride in Illinois

Author: , October 9th, 2014

Gay Pride Boystown

Illinois Gay CoupleSo you missed summer in Chicago and all of the outdoor music fests and neighborhood block parties that come with it? Never fear! There is so much to do in Illinois in the fall and – as the 16th state in the nation to legalize same-sex marriage – we are proud to offer plenty of options for LGBT couples looking for a fun and friendly getaway.

Whether you are looking for romantic hideaways to escape and unwind or exciting cities to explore vibrant LGBT neighborhoods, we have it here in Illinois. From Chicago’s bustling Boystown scene, to picturesque Galena on the western border of Illinois, to the state capital of Springfield to the sprawling Shawnee National Forest in the southern region, there is so much for couples to see and do in Illinois. At all of these destinations, you’ll find Travel Alternative Group (TAG) approved hotels, certified based on their diverse staff and commitment to the LGBT community.

Chicago – Boystown

Boystown, ChicagoOut Traveler recently named Chicago’s Boystown as the best gay neighborhood in the world based on reader votes. That’s right… in the world! Boystown was the nation’s first officially recognized LGBT village in the United States and continues to be a popular destination for locals and travelers today.

To celebrate its rich history and progress, the neighborhood plays host to Chicago’s Pride Parade & Pride Weekend every summer, one of the most legendary LGBT celebrations in the world. As someone who frequents the neighborhood’s restaurants, art galleries, shops and bars, I can vouch that it really is the best… and it is continuing to get even better!


GalenaAbout a three-hour drive from Chicago, Galena is home to charming bed and breakfasts, great shopping and celebrated wineries. The European-style town on the Mississippi River is a wonderful place for couples to escape on a romantic retreat. Stroll along Historic Main Street to see nineteenth-century storefronts and dine at nationally acclaimed eateries, such as the Log Cabin Steakhouse and One Eleven Main.

Don’t leave without paying a visit to Miss Kitty’s Grape Escape Lounge, a local favorite with great cocktails and, of course, the famous Miss Kitty!


Abraham Lincoln Presidential Library and MuseumHistory comes alive in Springfield, located in central Illinois. Home to more Abraham Lincoln sites than anywhere else in the nation, the capital city is a great place for couples to have an education experience together. Explore the Lincoln Home, Abraham Lincoln Presidential Museum & Library and Lincoln Tomb to discover the legacy of one of our nation’s greatest Presidents.

While at the Lincoln Tomb, rub the nose on Abe’s bronze statue for good luck. Springfield is also home to one of Illinois’ largest LGBT celebrations, Springfield PrideFest. Mark your calendars for May 16, 2015, which will be the city’s fifth annual celebration!

Shawnee National Forest

Shawnee National ForestActive couples who want to get out and explore nature should consider vacationing in the Shawnee National Forest in southern Illinois. The region’s hiking trails, bike paths, and lakes for fishing and swimming offer endless activities, and nothing is more romantic than the expansive view from the Garden of the Gods lookout point! After exploring by day, relax at a cozy bed and breakfast, woodsy resort or even luxurious treehouse!

Happy travels!

This article was written for Purple Roofs by Jen Hoelzle, Illinois State Travel Director. For even more trip ideas in Illinois, visit and make sure to check out the “LGBT Travel” Trip Ideas section.

Illinois Gay Travel Resources

If You’re in the Closet, Chicago May be the Travel Destination for You

Author: , September 9th, 2014

ChicagoWe have plenty of data on where gay men like to vacation — but what about men who aren’t out of the closet?

According to a recent poll by, the most popular destination for closeted gay men in the world is Chicago, Illinois, followed by Sydney, Australia. A press release from the site claims that over 5,000 “male members seeking male travel companions” were initially polled to learn if they were out and the 41% “who were in fact closeted were then surveyed to discover their top destinations for discreet travel.”

“With gay marriage recently being recognized by the state of Illinois, it is not surprising that many closeted men are flocking to The Windy City,” Brandon Wade, Founder & CEO of, said in a statement. “Chicago offers a wide variety of gay-friendly attractions that complement the midwestern values the city was founded on.” The press release for the survey also noted that Chicago “is a business hub, making it a plausible destination for prudent travel” and that “all cities that made the final cut were gay-friendly destinations that also catered to a heterosexual audience.”

By James Nichols – Full Story at The Huffington Post | Illinois Gay Travel Resources

Chicago Pride This Weekend

Author: , June 21st, 2014

Gay Pride Portland

Chicago’s Pride Weekend kicks into high gear this weekend with the 12th annual Chicago Pride Fest, a week before the 45th annual Pride parade. The event opens at 11 a.m. Sat., June 21 and runs through Sun., June 22 in Boystown.

Chicago native, Oscar-winning actress and Grammy-winning musician, Jennifer Hudson (interview), is returning back to her roots in the Midwest to give an explosive performance on Sat., June 21. And, organizers are calling her the biggest act ever secured for a Boystown summer festival.

“Bigger is better is not just marketing speak,” said Ramesh Ariyanayakam president of the Northalsted Business Alliance, the group behind Pride Fest and Market Days. “From our headliner Jennifer Hudson to the multitude of other top quality performers like Betty Who and Carlito Olivero, we have the most comprehensive line-up in the festival’s history.”

By Full Story at GoPride | in Illinois Gay Travel Resources | Other Gay Travel Events

Jennifer Hudson is Excited About Her Chicago Pride Performance

Author: , May 29th, 2014

Jennifer HudsinJennifer Hudson says she’s “excited” to headline Chicago Pride Fest, the Windy City’s annual 2-day street festival which takes place the weekend before the city’s annual Pride Parade in June.

The 32-year-old Hudson discussed her Saturday, June 21 performance with

When asked, “How would you describe what your LGBT fans mean to you?” Hudson replied: “Oh, my God! I would have to say everything. That’s where I started. I always say it was the gay community that loved me first. It feels good to come full circle and get back into that. I am so excited!”

via On Top Magazine | Illinois Gay Travel Resources | Other Gay Travel Events

International Mr. Leather Debuts Tonight

Author: , May 23rd, 2014


Get ready Chicago! The 36th annual International Mister Leather (IML) competition is returning to the Windy City full of parties, celebrations and weekend events. IML, one of the biggest leather and fetish events in the world, brings thousand of leathermen to town.

In addition, two well-known DJs will be headlining IML festivities this year. Eddie Martinez spins the Victory Party, which celebrates the announcement of the new International Mr. Leather 2014, on Sunday, May 25 at the House of Blues, 329 N. Dearborn, and David Picard takes over the turntables for the Black & Blue Ball on Monday, May 26 at Castle Chicago, 632 N. Dearborn.

Martinez, who was born and raised in NYC, has a passion to making listeners dance.

“I have been DJing for about nine years and working as a DJ for the past five years,” he told “My passion came from my love for music. Ever since I was a little boy, I would always dance around to pretty much anything and everything and I still do.”

By Denny Patterson – Go Pride | Illinois Gay Travel Resources | Other Gay Travel Events