Chicago's most provocative museum, one of the largest modern art museums in the United States, exhibits art that's A) thought-provoking and B) created post-1945 (hence the "modern" part). The art umbrella covers painting, sculpture, photography, video, film and performance; its 6,000-piece collection includes works by Roger Brown, Chuck Close, Alexander Calder, Sol LeWitt, Andreas Gursky, Christo and Andy Warhol. Seeing is believing, but you can get an earful, too, thanks to regular lectures and daily 45-minute tours (free with museum admission).
Designed by architect Josef Paul Kleihues, claustrophobia has no place in the airy space. The extensive granite front steps are a wonderful place to sit while waiting for friends; they front a plaza that host a can't-miss farmers market come summertime. And that's not all events-wise. The first Friday of every month features the eponymous "First Fridays," a 21+, cash-bar event which runs from 6-10 p.m. Your $14 ticket ($7 members or $10 in advance for non-members) includes museum admission, an ecletic mix of cultural happenings (performance art, music and the like) and hors d'ouevres by Wolfgang Puck.
Other features include a 300-seat theater where the visual and performance arts intersect, showcasing the latest in experimental film, music, dance and performance art. You can eat lunch at the in-house Puck's at the MCA (which features a Sunday brunch that's well paired with some leisurely art going), then pick up a souvenier or bit of reading at the store/bookstore.
The MCA is located just east of the Water Tower, with a sculpture garden that extends toward the Lake. Admission is $10 general; $6 students and seniors; free for members and children (12 and under). Ease the strain of your wallet by visiting Tuesday from 5-8 p.m. if need be, when the entrance price is waived.