Although I never been in Chicago I asked Google and made a little research and that was the answers:
1. Intelligentsia Coffee
3123 N Broadway St, Chicago, IL
This casual coffee bar proves it's possible to be hip and homey at the same time.
2. Kafein
1621 Chicago Ave, Evanston, IL
Northwestern students kick-start their days with fancy coffee drinks in a mock-Renaissance, intellect-friendly setting.