Pints, Pooches & Parties; Oh Mayfest! May 10, 2012 I love the city of Chicago! No, really I do. Especially in the summer time! There’s always something going on, right? Well, if you didn’t know that and find yourself bored on the weekends you can look forward to festival season. It’s quickly approaching and the city and burbs (yes, I know it’s suburbs) offer a variety of activities during the warm months. From the middle of May till the end of September, you can catch something every weekend.