What exactly is the vibe in Chicago during the month of October? Our guess is, it doesn't matter what time of year it is in Chicago, it's a certainty that the city is full of fun and stuff to do. It's just that exciting of a place to be.

Yea, Chicago is known for its brutal winters, but in early October, we don't think it will be that way...or will it?

Anyway, it's become a fact that Justin Timberlake will be performing at the United Center in the Windy City on on Friday October 5th of this year (2018 for those who are not sure.)

And it just so happens, you have a chance to fly out to Chicago and see J.T. rockin' the stage of the United Center. The winner of this fabulous prize package will get Two (2) VIP tickets to the show, roundtrip airfare for two (2), two (2) nights hotel stay and of course, 500 spending cash to use anyway you want to.

How do you enter this awesome getaway? Glad you asked. There are a few ways you can enter and get additional entries. Just click on the lovely blue button below (it is blue, right?) and follow the easy instructions. You must be 18 or older to win. Entry deadline is July 13th, 2018.

Good luck, and if you win, take pictures and let us know how much fun you had!