I have $1000 and a weekend, where should I go?

I live in downtown Chicago. My job got bought out and I feel like celebrating/taking my mind off of it/vacationing before my "favorite thing in the world" becomes my "job" again. What is the most fun an American can have for $1000 and a weekend? I can fly anywhere in the country, take a train/bus/drive somewhere, or just hang in Chicago; whatever is the most fun. <br><br>I'm a 30-yr-old, single, male software engineer with no cap on PTO anymore. I have a passport/Global Entry and valid drivers license.<br><br>Longest travel time acceptable: 5 hrs.<br><br>I'm up for anything: beach, wilderness, city, partying, chilling, whatever. No drugs though.<br><br>Bonus points if it's something I wouldn't think of.<br><br>My list:<br><br>- Miami<br>- Nashville<br>- KC<br>- New Orleans<br>- Austin<br>- NYC (probably too expensive)<br>- Chicago side quest<br><br>What other ideas do you have?