I live in a Chicago neighborhood originally settled by German immigrants. There are hits of both Bavarian and Northern Saxony culture in every nook and cranny as far as the eye can see. One of which is the massive May Pole that lives in a corner of what is now a parking lot. It stands there all year round, but today it is decked out with beautiful ribbons (not unlike this photo that I grabbed from a Google search because I am not in my 'hood, but in the Loop today J). May Day always feels like summer is right around the corner for me and if you aren't familiar with summer in Chicago, I can tell you that summertime is the best time.
As a Chicagoan, I feel it is my obligation to cram in as much fun a frivolity into those 3 small months as possible and the absolute best way to kick off the season is Mayfest held just under that very same May Pole. Don't be confused by the name though, as Mayfest actually begins June 1st. Such is life in Chicago!