#1 Benefit
The prestigious ball, which is used as a model fund-raiser for other society chapters, raised $2.1 million this year. Nearly 900 guests and volunteers gathered at the Radisson Blu Aqua Hotel for a night that included entertainment from comedian Billy Gardell and high-style design from Heffernan Morgan Ronsley. During the always-lively auction, a golden retriever puppy fetched an $84,000 bid. Next: April 26, 2014
#2 Benefit (new to the list)
Some 3,500 guests turned out to this year's Willy Wonka-theme event, marking a record attendance. A benefit for the Gateway Green, the ball is one of Chicago’s best-known benefits and is particularly popular among the young-philanthropist crowd. Next: September 2014
#3 Benefit
The huge gathering at McCormick Place traditionally draws 2,000 guests and raises more than $3 million. Smokey Robinson is slated to perform at this year’s event. Next: December 14, 2013
#4 Benefit
The event raises around $2 million each year and draws 1,700 guests. Celebrity attendees have included Steve Harvey, Phylicia Rashad, and Gladys Knight. Next: November 9, 2014
#5 Benefit
The glitzy night at the museum raked in more than $2 million this year and had unusual auction prizes: one guest bid $10,000 to drink out of the Stanley Cup. The evening also featured a surprise performance by Buddy Guy and drew nearly 900 guests. Next: Fall 2014
#6 Benefit (up from #9)
Dubbed “A Fair to Remember: Chicago, 1893,” this year’s event let guests tour the temporary exhibition "Opening the Vaults: Wonders of the World’s Fair." The gala drew 700 guests and raised $2.1 million. Hanging Ferris wheels played into the decor. Next: October 25, 2014
#7 Benefit (up from #15)
Including a performance from local teens, this year’s event drew 900 guests and raised more than $2 million. Mayor Rahm Emanuel was in attendance, as were former Mayor Richard M. Daley, board chair Mellody Hobson, and Hobson’s husband, filmmaker George Lucas. Next: Fall 2014
#8 Benefit (up from #11)
With a superhero theme, the black-tie event included an appearance from comedian Martin Short and had higher production levels than in years past. It raised $1.3 million and saw 800 guests. The event also included video messages from actor Steve Carell, chef Rick Bayless, and more notable figures. In 2014, the event will move to a larger space at Soldier Field. Next: May 3, 2014
#9 Benefit
An author is seated at each table at the prominent fund-raiser, which draws international leaders in the literary industry. This year, honorees were Isabel Allende and Michael Lewis, and the event raised more than $1.5 million. The event drew a record-breaking 750 guests. Next: Fall 2014
#10 Benefit
With a James Bond-inspired theme, this year’s gala showcased the new stingray exhibit and included an aquatic show, a dinner, and an after-party with a lavish dessert spread. It drew some 900 guests and raised more than $1.2 million. Next: June 7, 2014
#11 Benefit
More than 600 guests attended the museum's black-tie event, which raised more than $1.5 million. Guests took a tour of the butterfly sanctuary, and the evening’s then-new exhibit, “Savour Nature,” inspired vegetable-filled decor. Next: May 2, 2014
#12 Benefit
With a “Wild at Heart” theme, the summer gala raised more than $1 million for the Chicago institution. More than 900 guests attended, and there was a surprise performance from KC and the Sunshine Band. Next: July 11, 2014
#13 Benefit (up from #21)
This year, the event broke records in both attendance and funds raised: it drew 900 guests and raked in $1.5 million. A Mother’s-Day-weekend tradition, the gala is chaired by Rita Hayworth’s daughter, Princess Yasmin Aga Kahn. Next: May 10, 2014
#14 Benefit (up from #16)
The black-tie gala always gets a whimsical spin in honor of its young beneficiaries. New to this year’s event is a “science fair for grown-ups” during cocktail hour. Organizers expect 1,000 guests—up from 900 in 2012. Next: December 14, 2013
#15 Benefit (up from #17)
Held at Navy Pier’s Grand Ballroom, the event typically draws 850 guests representing Chicago’s business, medical, and social communities. This year, the association's big benefit raised more than $1.7 million. Next: April 12, 2014
#16 Benefit
With the theme “Oh, What a Night,” the gala this year drew nearly 1,100 guests and netted a record $1.4 million for the medical center and Advocate Children’s Hospital. The event’s ‘60s theme carried through to a dinner that included deviled eggs and wedge salad. Next: May 3, 2014
#17 Benefit
A costumed Ronald McDonald roamed the black-tie event for 900 guests. Held at the Sheraton Chicago Hotel & Towers, the gala had a masquerade theme and pulled in $900,000 for the organization. Next year’s event will have an Emerald City theme. Next: March 8, 2014
#18 Benefit
Chicago’s top-name chefs serve hors d’oeuvres at the glitzy evening for 750 guests. Presented by Fairmont Hotels and Resorts, the evening also includes a presentation of the Jean Banchet Awards for Culinary Excellence. In 2014, the event will have a St. Tropez theme. Next: January 31, 2014
#19 Benefit
With an “Into the Wild” theme, this year’s gala at Navy Pier drew more than 700 guests. The tropical theme translated into 15-foot trees decked with stuffed-animal monkeys and a tinsel waterfall that cascaded toward the dance floor. The event raised more than $1 million. Next: June 14, 2014
#20 Benefit (up from #22)
With more than 650 guests in attendance, this year’s event had an “Infinite Horizons” theme and decor in night-sky hues. It raised more than $1 million. Next: Fall 2014
#21 Benefit
During cocktail hour, the 625 guests interacted with a pink flamingo and a sloth; during dinner, a cheetah appeared on the dance floor. The animal-centric event grossed more than $1.24 million. Next: April 26, 2014
#22 Benefit
With a crowd of 500 guests, this year’s event was dubbed “the Crystal Ball” and had decor in hues of white and grey. It took place at the Radisson Blu Aqua Hotel and raised $1.1 million. Next: May 2014
#23 Benefit (up from #24)
The elegant summer event draws the cream of North Shore society to the grounds of the Chicago Botanic Garden. This year’s dance had a “Language of Flowers” theme with Victorian-inspired decor, and it raised $500,000. Some 350 guests attended. Next: June 13, 2014
#24 Benefit
Held at the Peninsula, the event this year drew more than 300 guests and raised more than $500,000. It offered entertainment from DJ Chris Cater, and the live-auction prizes included earrings from Harry Winston. Next: September 2014
