Since June of this year, I have been working at my client's in Central Illinois, so I decided to take the opportunity to visit my BFF in Chicago over the weekend.
During the summer, there are plenty of festivals in the city. Lots of bands, food, booze and people watching. We were there during the Wicker Park Festival, which was super fun. The key (IMHO) is not to get the beer/sangria from the beer stands and stand around drinking. Instead, score seats on the patio at one of the bars right by the festival. That way you get more drink/cocktail & food options, and you get to sit your butt down while still getting in the music and people watching. It wasn't overly crowded at the festival - no nudging your way through the crowd.
A fun thing to do in Chicago is to attend a concert at Ravinia, an outdoor music festival spot in Highland Park (We attended the James Taylor concert and it was sold out). You can hop on the Metra in downtown and it's a short 30 minutes train ride (we drank on the train too!). The trains drops you right at the venue entrance, and when we left, the line to get on the train was much faster and efficient than people trying to take the shuttle back to the parking lot.
Sometimes it's nice to take a break from the bars & restaurants, and just picnic and listen to some good music