
#1 Festival
The festival drew a record-breaking 100,000 music fans per day to Grant Park last year with about 130 acts. And to attract top ticket holders, a new Platinum Pass granted unprecedented perks like an open bar and elevated viewing areas. This year’s event will feature headliners such as Eminem, Outkast, and Kings of Leon. Next: August 1-3, 2014

#2 Festival
Founded in 2006, the increasingly popular event draws an average of 18,000 fans per day and—with weekend passes going for $120 a pop—is appreciated as one of the more affordable major music fests. This year’s event will offer performances from Beck, Neutral Milk Hotel, Kendrick Lamar, and more. Next: July 18-20, 2014

#3 Festival
Chicago Gourmet, produced by the Illinois Restaurant Association and presented by Bon Appétit, is arguably the city’s most prestigious food and wine event. There were more big-name chefs than ever in 2013—a total of 175 participated—and there was also more food. This year, Chicago Gourmet introduced a new quarterly event called “Beyond Gourmet: The Dinner Series,” which is designed to showcase the city’s culinary landscape. The fest sees an average of 6,000 guests per day. Next: September 26-28, 2014

#4 Festival
There was good news for Chicago’s signature food festival last year: the fest was profitable for the first time since 2007, generating $272,000. Attendance also increased with 1.5 million guests compared to 1.2 million in 2012. This year, headliners for the nightly concerts include Janelle Monae, and a new “Made in Chicago” pop-up shop will offer goods from non-food artisans. Next: July 9-13, 2014

#5 Festival (up from #6)
In 2013 the event relocated from Grant Park—which, some guests complained, had subpar acoustics—and set up shop in Millennium Park. Last year’s fest also had Friday-afternoon concerts, which had not been offered since 1997, and estimated attendance was 125,000. Next: August 28-31, 2014
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#6 Festival (up from #5)
The summertime tradition was significantly scaled down in 2013 due to federal budget cuts. Gone were the beloved Blue Angels and the Thunderbirds—but they will return this year. Some 1.7 million spectators took in the event last year, but attendance is typically closer to two million. Next: August 16-17, 2014

#7 Festival
Held in mid-June, this year’s event featured performances from Carolina Chocolate Drops, Otis Taylor Band, and more. It's the world’s largest free blues festival and typically draws more than 500,000 fans throughout its three-day run. Sponsors include Pepsi and Bud Lite. Next: June 2015

#8 Festival
The outdoor classical-music festival celebrates its 80th anniversary this year. It kicked off with a “Tchaikovsky Extravaganza” in June and will run through mid-August with Millennium Park concerts highlighting Mozart, Berlioz, and other composers. The season will also offer performances in various Chicago neighborhoods. Next: Summer 2015
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#9 Festival (up from #11)
Presented by The Chicago Tribune, the festival is the Midwest’s largest free, outdoor literary event. This year, the book fair celebrated its 30th anniversary with more than 200 authors, performers, and presenters. There was also a “Good Eating” stage with culinary demos from highly regarded chefs such as Lidia Bastianich. Next: June 2015
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#10 Festival
The largest weekend street fair in the Midwest usually draws 100,000 guests. Occupying six city blocks, last year’s fest offered three stages with entertainment from bands like Wilson Phillips. At this year’s iteration, nearly 300 vendors will offer food, arts, and crafts; the 40-plus musical performers will include Neon Trees and Karmin. Next: August 9-10, 2014

#11 Festival
The largest annual outdoor dancing series in the United States is held in Grant Park’s Spirit of Music Garden. It offers free dance classes on a 100-percent-recyled, open-air dance floor, and classes cover styles ranging from swing to waltzing. Chicago SummerDance sees some 1,200 participants gather at each session; this year, 44 bands will perform. Next: June 27-September 14, 2014