When Frank Sinatra says that Chicago is his kind of town, what other endorsement do you need? Chicago is a big city with a small town feel.

I have only been to Chicago once, but it is one place on my list to get back to. It is a great city, but without that big city vibe. Not only is there a ton to do there, but in the summertime it is breathtaking!

No matter what you like to do, you will find it in Chicago. When I was there, we had a chance to meet Michael Jordan. He is easily one of the nicest celebrities I have ever had the chance to meet.

If you think you would would love to visit Chicago, but it's just not in the budget right now, then you are in luck. We are giving away a trip to Chicago to see Taylor Swift on July 18th!