6. Chicago, IL
Flight costs: $265
Attractions: Art fairs, music festivals, summer fireworks, food fairs, dance festivals
If you are a music lover, a summer in Chicago should be part of your bucket list. They have tons of music festivals in June alone. They have Spring Awakening Music Festival, Country LakeShake Music Festival, Chicago Blues Festival, and Chicago Gospel Music Festival, among many others. There are also street art fairs and food festivals you wouldn’t want to miss.