1. Taste of Chicago
The 30th iteration will occupy Grant Park June 25 to July 4. More than 50 local restaurants will sling samples of signature dishes, and a to-be-announced slate of big-name artists will put on free shows. Around 3.3 million guests attended in 2009.
2. Chicago Air and Water Show
Billed as the nation’s largest spectator event, this 52-year-old show features daredevil stunts from civilian and military aviators. Some 2.2 million guests are expected to pour in from around the Midwest for the next iteration on August 14 and 15.
The music fest will return to Grant Park August 6 to 8, with seven main stages and an expected crowd of 75,000 per day. The event has drawn bands such as Kings of Leon and Tool, an international stream of tourists and press, and support from brands such as PlayStation, Dell, and Honda.
4. Chicago Blues Festival
The world’s largest free-admission blues festival will bring six stages to Grant Park June 11 to 13, drawing an estimated crowd of 600,0000 music lovers. Some of the genre’s biggest stars—including Bonnie Raitt, Ray Charles, and B.B. King—have performed here.
5. Chicago Jazz Festival
Legends such as Miles Davis have taken the stage at this gathering, which draws an average crowd of 310,000. The event takes over Grant Park on September 4 and 5 with CareFusion as a new sponsor. Chicago Community Trust will back the Young Jazz Lions Stage, the festival’s first new stage in a decade.
6. Pitchfork Music Festival
Some 52,000 music fans—40 percent of them from outside Illinois—are expected at this year’s festival, which takes over Union Park July 16 to 18. The lineup typically includes about 40 acts; Pavement and St. Vincent will perform this year. Online indie music bible Pitchfork hosts, and Nintendo and Motorola have sponsored.
7. Grant Park Music Festival
Developed by Mayor A.J. Cermak as a spirit-booster during the Great Depression, this is the country’s oldest free outdoor classical-music concert series. Set for June 16 to August 21, the festival will feature works by Vivaldi and Beethoven. Some 8,000 people attend a typical concert.
8. Chicago SummerDance
With more than 1,200 participants each, three weekly classes offer free instruction in everything from salsa to polka. At the end of each class, live musicians play while guests try out new moves in Grant Park’s Spirit of Music Garden. This year’s alfresco dance party will take place June 17 to August 29.
9. Printers Row Lit Fest
The region’s largest literary festival, this downtown event offers more than 200 panel discussions. Other activities include cooking demos, writing workshops, and poetry slams. The 2010 fest is scheduled for June 12 and 13, and 125,000 attendees are expected—a boost from last year’s crowd of 110,000.
10. Chicago Country Music Festival
Taylor Swift and Miranda Lambert have headlined this showcase, which features three stages, an art fair, a farmer’s market, and a dance tent. Tentatively scheduled for September 18 and 19, the down-home extravaganza will draw around 100,000 people to Millennium Park.
11. Northalsted Market Days
Known as the Midwest’s largest weekend street fair, this event occupies six city blocks and draws 40,000 attendees. Forty acts perform, and some 400 vendors hawk food, arts, and crafts. The 2010 event will fill North Halsted Street on August 7 and 8.
12. Chicago Gourmet
After its inaugural run in 2008, the Illinois Restaurant Association’s gourmet festival returned to Millennium Park last year with twice as many tasting stations, 100 more wine vendors, and 8,000 guests—compared with 6,500 the first year. The event returns September 25 and 26.