1. Taste of Chicago
More than 3.5 million people come to Grant Park each summer to sample dishes from around 70 Chicagoland restaurants during the Taste of Chicago. The free 10-day festival, now in its 27th year, took place June 27 to July 6 this year. In addition to tents full of food offerings, the event included an ongoing lineup of entertainment at the Petrillo Music Shell, with acclaimed artists like Stevie Wonder and Chaka Khan performing.
2. Chicago Air & Water Show
Though there are plenty of water-based performances at this 50-year-old city-run show, the military and civilian aircraft have traditionally been the real draw. This year, close to two million people are expected to crowd the lakefront to catch the show over the weekend of August 15 to August 17. An extra day has been added to the 2008 festivities in honor of the event’s golden anniversary, and will feature more aerial acrobatics, a free concert, and a fireworks display.
3. Chicago Blues Festival
The world’s largest free-admission blues festival brings more than 750,000 people to Grant Park each June. With more than 80 performers, it showcases the entire spectrum of the blues, from old harp players to electric guitarists. The 2008 event, which marked the festival’s 25th year, took place June 5 to 8, and featured artists like B.B. King and Koko Taylor.
4. Venetian Night
Thematically decorated boats light up the night at this event, now in its 51st year (making it the longest-running event produced by the city). About 35 boats sail along Lake Michigan between the Shedd Aquarium and the Chicago Yacht Club as more than 675,000 spectators—some of whom grab spots as early as 9 a.m.—watch from along the lakefront. In addition to the parade, the event features a live concert and a fireworks show. The 2008 Venetian Night will be held July 26.
5. Chicago Jazz Festival
This festival showcases a range of talent, from legends (like 2008 headliner Ornette Coleman) to younger artists (like 2007 performers Medeski Scofield Martin and Wood). The 30-year-old festival is organized by the city and programmed by the Jazz Institute of Chicago. After about 315,000 people attended in 2007, a fourth day was added to this year’s lineup, which will take place August 28 to 31 and feature a free Thursday night concert in Millennium Park.
6. Chicago Gospel Music Festival
The festival—which draws around 260,000 spectators a year—is held annually in Millennium Park and sees more than 50 performances over the course of three days. For this year’s 24th annual event, which took place May 30 to June 1, church choirs, family groups, and finalists from BET’s Sunday’s Best performed on two stages. The event also featured a youth tent where local choirs and quartets sang.
7. Chicago Country Music Festival
Traditionally, the city’s two-day Country Music Festival (founded in 1991) occurs in Grant Park during the first weekend of the Taste of Chicago, making it easy to enjoy down-home cookin’ with the down-home tunes. But this year, the festival is going it alone on October 11 and 12 in a new location (just outside Soldier Field). New additions include a third stage, a dance tent, and a kids’ tent.
8. Chicago SummerDance
School is in session throughout the summer at the Spirit of Music Garden in Grant Park, where Chicagoans gather on Thursday, Friday, and Saturday evenings and Sunday afternoons, to learn dance moves from professional instructors. Between 1,200 and 1,500 people attend each session, which cover everything from salsa to swing, and each class is followed by a concert from a genre-appropriate band. This year’s 12th annual SummerDance, which is currently taking place (it runs from June 12 to August 24), features three new events at Navy Pier.
Though it’s only been held in Chicago since 2005, Perry Farrell’s formerly touring musical extravaganza (produced by Austin, Texas-based C3 Presents) has become a major city festival—and will remain so until at least 2011. More than 150,000 fans from across the U.S. come to Grant Park for the three-day concert, which features 100-plus acts on nine stages. Radiohead and Rage Against the Machine are among the headliners for this year’s event, which comes to town August 1 to 3.
10. Northalsted Market Days
Run by the Northalsted Area Merchants Association, this gay-friendly, two-day street fair is the largest of its kind in the Midwest, drawing upward of 150,000 people each year. In the Boystown section of the Lakeview neighborhood, the 27-year-old event features roughly 400 food, art, and craft vendors and more than 40 musical acts—many of them nationally known artists like Big Brother and the Holding Company and Cathy Richardson. The 2008 Market Days will take place August 9 to 10.