One of the best places in Chicago to get your drink on is the end of the pier at Loyola Park. It's got great outdoor seating with a world class view of Chicago's lakefront and skyline. There is never a cover charge.
Just go to the east end of Pratt Avenue, just off of N. Sheridan Road. Walk to the end of the pier to the lighthouse. There you are! Watch the moon, howl at the moon, expose your moon, and have a drink. It's BYOB but there is not decanting charge.