1. Taste of Chicago
Now in its 28th year, Taste of Chicago took place June 26 to July 5 and welcomed around 3.5 million visitors. The 10-day festival, held in Grant Park, allows guests to sample dishes from more than 70 area restaurants.
2. Chicago Air and Water Show
The 51-year-old show is billed as the largest spectator event in the United States. The 2009 incarnation will take place August 15 and 16 and will draw an estimated 2.2 million spectators.
The 2009 Lollapalooza will bring more than 100 musical acts and an estimated 150,000 fans to Grant Park from August 7 to 9. The event lures a bevy of tourists, celebrities, and national press, and companies such as PlayStation, MySpace, and Dell sponsor areas on the festival grounds.
4. Chicago Blues Festival
Chicago is home to the world’s largest free-admission blues festival. Each year, more than 640,000 music lovers converge in Grant Park to take in concerts from the likes of Koko Taylor and B.B. King. This year’s festival took place June 12 to 14.
5. Chicago Jazz Festival
The 2009 Chicago Jazz Festival will draw some 310,000 guests to Grant Park from September 4 to 6. The event is recognized as the city’s oldest lakefront music festival, and has featured performances by Miles Davis and Wynton Marsalis.
6. Grant Park Music Festival
The country’s last free outdoor classical music series, this festival draws upward of 300,000 visitors to Grant Park each year and celebrates its 75th anniversary in 2009. This year’s season will take place June 11 to August 16.
7. Outdoor Film Festival
Each year, this event showcases classic American films on oversize screens in Grant Park’s Butler Field, and some screenings draw 30,000 spectators. The 2009 incarnation takes place Tuesday nights from July 14 to August 25.
8. Chicago SummerDance
From June 11 to August 23, an open-air dance floor in Grant Park will host this free-admission festival. Three weekly dance classes, which cover styles ranging from swing to Afrobeat, typically draw between 1,200 and 1,500 students each.
9. Northalsted Market Days
The Northalsted Area Merchants Association runs this weekend street fair, which sees an average annual attendance of 150,000. Craft vendors and musical acts fill the gay-friendly event, which takes place this year August 1 and 2.
10. Printers Row Book Fair
The Midwest’s largest literary festival was renamed the Printers Row Lit Fest and held June 6 and 7. Founded in 1984, the event typically draws some 1250,000 guests and features approximately 200 national booksellers and author discussions.
11. Chicago Country Music Festival
Taylor Swift headlined the 2008 Chicago Country Music Festival. The 2009 event will take place October 3 and 4 and is expected to draw 150,000 guests.
12. Pitchfork Music Festival
Held in Union Park, this festival hosted by the indie-music Web site Pitchfork has showcased artists such as Cat Power, Yoko Ono, and Spoon. The 2008 festival saw 50,000 attendees and featured 40 acts. This year’s fest returns in July.