
#1 BenefitÂ
The prestigious ball, which serves as a model fund-raiser for other society chapters, raised around $3.3 million this year—up substantially from $2.1 million in 2013. Held at the Radisson Blu Aqua Hotel, the night featured a live performance from country singer Keith Urban and had whimsical style ideas such as cocktails served from a lemonade stand. Next: April 25, 2015

#2 BenefitÂ
This year’s late-summer bash will have a Great Gatsby theme and will take place in a massive parking lot at the University of Illinois—Chicago. Some 3,500 guests turned out to last 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 13, 2014

#3 Benefit
The massive gathering, held at McCormick Place, traditionally draws 2,000 guests. Smokey Robinson performed at last year’s event, which raised a record $3.8 million. Mayor Rahm Emanuel was among the evening’s big-name guests. Next: December 13, 2014

#4 BenefitÂ
In 2013, the 52nd annual dinner raised $1.9 million and drew guests including Mayor Rahm Emanuel, Governor Pat Quinn, and Reverend Jesse L. Jackson Sr. Now in its 53rd year, the event typically draws around 1,700 guests. Next: November 9, 2014

#5 Benefit
The glitzy night at the museum raked in more than $2 million last 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: October 11, 2014

#6 Benefit (up from #7)
The well-known gala raises funds for the charity founded by Chicago’s beloved former first lady Maggie Daley. Including a performance from local teens, the 2013 event drew 900 guests to Navy Pier and raised more than $2 million. Attendees included former Mayor Richard M. Daley, board chair Mellody Hobson, and Hobson’s husband, filmmaker George Lucas. Next: September 23, 2014
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#7 Benefit (up from #8)
This year, the event became the first gala to take place in a tent on Soldier Field. Comedian Seth Meyers was the headline act, and the event raised $1.4 million (up from $1.3 in 2013). It also drew a substantially bigger crowd this year: while 840 guests attended in 2013, the 2014 iteration saw 940 guests. Next: May 2015

#8 BenefitÂ
Dubbed “A Fair to Remember: Chicago, 1893,” last year’s event let guests tour the temporary exhibition "Opening the Vaults: Wonders of the World’s Fair." The gala drew 700 guests, raised $2.1 million, and had an inventive decor scheme that featured hanging Ferris wheels. This year’s fall event will have a “Caribbean Rhythms” theme. Next: October 25, 2014

#9 Benefit (up from #10)
This year’s event had a Goldfish theme and featured a performance from Broadway star Susan Egan, who sang to a sea lion during the live animal show. With a tighter, more streamlined program this year, the event drew 800 guests and raised a record-breaking $1.67 million. Next: June, 2015

#10 Benefit (up from #13)
Chicago sports legend Mike Ditka served as M.C. at this year’s gala, which was held over Mother’s Day weekend at the Hilton Chicago. Chaired by Rita Hayworth’s daughter, Princess Yasmin Aga Kahn, the event drew 940 guests and raised a record-breaking $1.7 million (up from $1.5 million last year). Next: May 9, 2015

#11 Benefit (up from #15)
With the theme “Ignite,” this year’s event at Navy Pier drew some 850 guests representing Chicago’s business, medical, and social communities. To underscore the heart-health theme, guests had a healthy dinner of roasted cod with fig salad. In 2013, the association's big benefit raised more than $1.7 million—this year, it broke records by raising an impressive $2.6 million. Next: April 11, 2015
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#12 BenefitÂ
At this year’s event, authors Doris Kearns Goodwin, Larry McMurty, and Veronica Roth will be honored. In 2013, honorees were Isabel Allende and Michael Lewis, and the event raised more than $1.5 million. Also noteworthy: the event drew a record-breaking 750 guests. Next: October 22, 2014

#13 Benefit
With a “Wild at Heart” theme, the 2013 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. This year’s event will have a quirky “Monkey Business” theme and will offer mobile bidding via cell phones. Next: July 11, 2014
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#14 BenefitÂ
More than 600 guests once again attended the museum's black-tie event, which raised more than $1.52 million. With the theme “Abundant Nature,” the stylish fete featured decor from Event Creative. Tables were decked with prop firefly jars and yellow tulips, and Calihan Catering served a local, seasonal dinner. Next: May 2015

#15 Benefit
The black-tie gala celebrates its 56th year on December 6 at the Hilton Chicago. This year’s upbeat theme is “Big Dreams Bright Futures.” Last year’s event saw 1,000 guests—up from 900 in 2012—and it celebrated the $2 million raised throughout the year. Next: December 6, 2014
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#16 Benefit
With the theme “Fire and Ice,” this year’s springtime bash took place at the Chicago Marriott and featured a keynote address from Dr. Ian Smith. Some 850 tickets to the event were sold, and the event netted more than $900,000. Next: Fall 2014
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#17 BenefitÂ
With the whimsical theme “An Evening in the Emerald City,” this year’s gala drew 900 guests and raised more than $575,000. During cocktail hour, guests posed with actors dressed as Dorothy, Glinda, and other characters from the classic tale; a costumed Ronald McDonald also roamed around. Next: March 2015

#18 Benefit
The late-January fund-raiser took place at the Fairmont Chicago, Millennium Park. The evening drew 900 guests—up substantially from 750 last year—and included a special tribute to the late chef Jean Banchet. With a glitzy St. Tropez theme, the event netted a record-breaking $550,000. Next: January 2015

#19 Benefit
The event typically draws a crowd of 800 guests, who represent business, community, and civic leaders from Chicago. With an “Into the Wild” theme, last year’s gala at Navy Pier drew more than 700 guests and raised more than $1 million. This year’s event had a “Some Enchanted Evening” theme. Next: June 2015

#20 Benefit
With more than 650 guests in attendance, the 2013 event had an “Infinite Horizons” theme and decor in night-sky hues. It raised more than $1 million. This year’s event will have a “Starry Night” theme, and the evening will feature cocktails, dinner, and stargazing on the planetarium’s lakeside patio. Next: September 13, 2014

#21 Benefit
This year, the ball celebrated its 80th anniversary with an evening that included cocktails, dinner, dancing, and the opportunity for guests to pose for photos with a monkey. The “Around the Whirl in 80 Years” theme translated to decor that featured air balloons decking tables. The event drew 625 guests and raised $1.5 million. Next: April, 2015

#22 BenefitÂ
The 65th anniversary Woman’s Board Summer Ball took place at Navy Pier’s Grand Ballroom this year. It drew more than 500 guests, and it raised $1.3 million. Nine of the organization's past presidents served as co-chairs this year. Next: May 2015

#23 BenefitÂ
The posh summertime event draws the who's who of North Shore socialites and Chicago business leaders. This year's black-tie affair included a cocktail reception on the garden's Esplanade and dinner under a tent in the pavilion. HMR Designs' summery decor included peonies and a green-and-white color palette. Next: June 2015

#24 Benefit
Held at the Peninsula, the 2013 event 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: October 25, 2014
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