Chicago in the summer is 💯. I know I'm only hitting the tip of the iceberg here, so this list is open to suggestions!
  1. Lollapalooza
    You'll have to pay an arm and a leg, but this amazing festival in Grant Park is worth it. It's such a beautiful, perfect setting in the middle of the city, and the lineup is generally great.
  2. Ravinia Festival
    Okay, this isn't in Chicago, but it's in my hometown suburb Highland Park. It is this gorgeous, large outdoor music festival venue where attendees can either picnic on the lawn or buy tickets to sit in the pavilion. There are restaurants on site, clean bathrooms which is a plus, and the lineup is also pretty incredible. There are shows all throughout the summer!
  3. Pitchfork Music Festival
    This festival is a little less expensive than Lolla, but just as fun. If you're into indie, under-the-radar music, this festival is a great way to meet likeminded people and discover new artists.
  4. Chicago Blues Festival
    All I can say about this is free music in Grant Park! Plus, Chicago has some really fantastic blues artists. Even if you think you're not into that type of music, it really is worth a visit just to see some masters play. Did I mention it's free?
  5. Chicago Jazz Festival
    See above
  6. Taste of Chicago
    Yes it's crowded and expensive, but it's definitely a scene. Where else can you try all of the famous Chicagoan artery clogging cuisines in one place? It's also in Grant Park, so if you need a break, you can go take a food nap in Millennium Park (which I have done).
  7. Wells Street Art Festival
    Come to see amazing artisan pieces and artist at work. People flock to this art festival, and for good reason. It's also a fun opportunity to look at beautiful artwork while day drinking with friends.
  8. Grant Park Music Festival
    Once again, free music all summer! Definitely check out the schedule and get there early to get a good spot. I once went to a free Guster concert on the 4th of July in Grant Park and ended up in the second row. Chicago is the best.