Chicago’s Most Fabulous Santa Speedo Run
Sidetrack bar, located in Chicago’s Boystown, organizes scantily-clad ho-ho-homosexual runners for Chicago’s Most Fabulous Santa Speedo Run. The event is more than an excuse to hang out your holiday decorations…
Chicago Cupid’s Undie Run
There are fewer things in this world that feel better than getting half naked for charity. Cupid’s Undie Run lets you live that dream in the winter, in Chicago. The run…
Dining Out For Life Chicago
Yes Chef! The perfect excuse to indulge in your culinary cravings AND do some good—it’s Dining Out For Life time! Grab your friends, your appetite, and maybe loosen those belts!…
Chicago Pride Fest®
Chicago Pride Fest is an exciting two-day street festival in Boystown held the weekend leading up to the Chicago Pride Parade with up to 100,000 expected to attend, celebrating LGBTQ+…
Windy City Black Pride
Bringing together the best, not to mention hottest, of the black community, Chicago has a lot to celebrate.
Northalsted Market Days
The Midwest’s largest two-day street festival, Chicago’s Northalsted Market Days® draws 100,000 people, spans six city blocks, and features three music stages with more than 40 top-name performers. The Boystown…
Chicago Underground Film Festival
The Chicago Underground Film Festival transformed itself from a hole-in-the-wall operation focusing almost exclusively on local product to the largest underground film fest in the country, with films and tapes…
Mr. International Rubber
This year marks the 29th anniversary of Mr. International Rubber and The Rubber Blowout Weekend! Join in the fun with gear intensive kinksters from around the globe for a weekend…
Halloween on Halsted Parade
Get in on the action by dressing in your Halloween best: slutty sailor, zombie, alien, demon twink, gay Chick-fil-a customer.
Tired of seeing baby pictures from friends of friends on your Facebook wall, then "like" us and get inspiring/interesting/crazy/jealousy-inducing photos, stories and tips to inspire a trip.
If you can't wait to get our next update, make sure you follow us on Twitter for the latest tips, news and deals to make your vacation as gay as you are. And let’s be honest, that’s pretty darn gay.