
#1 Fashion & Retail Event
Major players in the fashion industry have attended the 80-year-old fashion show, including designer Jason Wu and J. Crew creative director Jenna Lyons. This year’s event honored Chicago-based artist Nick Cave, who’s famous for his abstract Sound Suit sculptures. In addition to an award presentation and runway show featuring student looks, the night included a cocktail reception in Millennium Park. Next: Spring 2015

#2 Fashion & Retail Event
Chicago’s fashion week includes runway shows in Millennium Park and other locales. There are also citywide affairs including trunk shows and in-store parties. In 2013, the event included new pop-up shops in the park. Next: October 2014

#3 Fashion & Retail Event
Held each season and open to trade only, StyleMax takes place at the Merchandise Mart and displays women’s apparel and accessories from more than 2,000 lines. The show also showcases kids’ fashion, sporty clothing, and maternity wear. Next: August 9-11, 2014
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#4 Fashion & Retail Event
A highlight on the calendars of local socialites, the prestigious fashion show highlights local retailers; it also has a unique competition segment that lets guests act as judges. Fashion industry bigwigs such as Monique L'huiller and Wes Gordon have attended, and retailers including Neiman Marcus have sponsored. This year’s event will return to the Hilton Chicago. Next: September 19, 2014

#5 Fashion & Retail Event (up from #6)
With a headline performance from Jason Derulo, this year’s event will include an hour-long fashion show featuring fall fashions; an after-party will take place on the Harris Theater rooftop in Millennium Park. The event will once again benefit Ronald McDonald House Charities of Chicagoland and Northwest Indiana. In the past, headliners have included Sheryl Crow and Cee-Lo Green. Next: August 8, 2014

#6 Fashion & Retail Event
The charitable show displayed fall and winter trends to a crowd of 2,500 this year. Held at the massive Grossinger Auto Complex, the event had a “Super Sonic” theme in 2013 and offered restaurant tastings, spa services, and an after-party at Japonais. Reality TV star Kristin Cavallari hosted. Next: Fall 2014
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#7 Fashion & Retail Event
Held at the Donald E. Stephens Convention Center in Rosemont, the event draws more than 1,300 guests. It includes a champagne reception, a raffle, a luncheon, and a designer fashion show. This year’s function will feature Allison Rosati of NBC 5 news as its anchor. Sponsors include Revel Global Events and Pepsi. Next: November 2, 2014

#8 Fashion & Retail Event
This year, the longstanding Chicago tradition celebrates its 88th anniversary. It is billed as the longest continuously running charitable fashion show in the country. With the theme “Imagine,” the event will take place at a new venue: Morgan Manufacturing. The Woman’s Board has pledged to raise $500,000 for technology that will help treat brain tumors. Next: October 2, 2014