Arrive at O'hare Airport and jump on an 'L' train towards Downtown Loop. You're going to transfer from Blue to Red at the Washington stop, and then get off at Belmont where you'll find your hotel, City Suites Chicago, an incredibly gay-friendly artsy hotel near all the action in Boystown. Seriously, you're going to love that your hotel is in this location by the end of the night.
After you've dropped your bags off and settled in, grab some lunch at Nookie's, a classic American comfort food stop that'll kill the hunger before you start your day of bar hopping and dancing.
Depending on your mood, you might want to relax in a hot tub or steam room down the street at Steamworks Chicago, particularly if you're a gay man.
By this time hopefully it's past 4 or 5 pm, which means bars are starting to open!
Dinner should definitely be in your night, or at least some decent bar food. Chicago Diner is classic if you want vegan or vegetarian food, or try Wood (modern cuisine and ritzy cocktails) if you're feeling slightly fancier.
Walk back up to Halsted and Cornelia around 9 pm, it's time to Hydrate at one of the most bouncy and in-your-face gay dance bars in the city. The dancing might not go super hard until at least 10 or 11 pm, but you can always change that. There are usually some pretty epic nights with extravagant drag performance or karaoke.
You're wired and it's only midnight! Catch a cab up to Big Chicks if you're thirsty for a queerer scene or just more ladies in general. If you're lucky, you'll catch a Friday night FKA dance party.
Take another cab back down to Belmont Avenue and end your night, like every other gay person in the city, at Berlin nightclub - hopefully on a Madonna or Robyn night.
And now be happy about your hotel choice when you are done dancing. It's right across the street.