Are there a fair number of concerts and festivals in Chicago like this weekend's Lollapalooza?

BluesFest in Grant Park is free (June 13-15. JazzFest, another free (Millennium Park) music event, is held over Labor Day weekend - this year Aug 28-31. Annual summer concerts at Wrigley Field have included Paul McCartney, Sting, and (this year) Billy Joel. Another major music event is Pitchfork - this year, it's being held July 18-20... http://pitchforkmusicfestival.com/ .

Chicago is a big market, and brings in good acts. We get Lollapalooza, but also Ozzfest and a ton of other concerts that come through, including Paul McCartney, The Rolling Stones and many of the more hip acts of today (I'm relatively young but I never hit up the concert scene anymore so I'm not fully aware of everything that goes on).