
#1 Benefit
In 2015, the prestigious benefit netted more than $2.9 million and drew 750 guests. Because of its success, the gala has served as a model fund-raiser for other chapters of the society. In addition to raising serious funds, the event showcases unique style ideas. This year’s theme was “Accelerating the Cure,” and HMR Designs’ decor was inspired by the speed of light. Comedian Paul Reiser also performed. In 2016, the event will celebrate its 10th anniversary. Next: April 2, 2016

#2 Benefit (up from #6)
This year, the gala raised $4.9 million for the charity that benefits local teens. The 1,000-guest event was held on Navy Pier, and co-chairs included Ariel Investments president Mellody Hobson and director George Lucas (Hobson’s husband). Throughout the evening, After School Matters teens performed and showcased their artwork. Next: September 19, 2016

#3 Benefit
Formerly known as the Chance of a Lifetime gala, the event was given a new name in 2014. Last year, the enormous fund-raiser drew 2,000 guests and was staffed by 350 volunteers; it raked in more than $4.1 million. This year’s event will take place in December, and the headline act is REO Speedwagon. Next: December 12, 2015

#4 Benefit (up from #7)
The ball had its most successful fund-raising year to date in 2015, bringing in $2 million for Make-A-Wish Illinois. (Last year, it raised $1.4 million.) Headliner Jay Leno performed, and unique auction lots included tours of Leno's Big Dog Garage. Some 960 guests attended. Next: May 21, 2016

#5 Benefit (up from #9)
With a “Metamorphosis" theme, this year’s event drew a record-breaking $2 million (up from $1.67 million in 2014). Some 770 guests attended the function, which featured an aquatic show, a paddle raise that brought in $280,000, and a creative Sodexo dinner that featured edible terrariums. Next: June 11, 2016

#6 Benefit (up from #14)
Attendance at this year’s springtime gala was 760, which was considerably higher than the 600-guest attendance in 2014. The event raised more money this year as well, bringing in $1.85 million as opposed to $1.52 million the previous year. Highlights of the annual event include a cocktail-hour tour of the museum’s butterfly house; guests also have the opportunity to chat with museum scientists. Next: May 6, 2016

#7 Benefit (up from #8)
Hosted by the Women’s Board of the Field Museum, this year’s gala had a “Wonders of China” theme inspired by a current exhibition. Blue Plate created a thematic meal, complete with Mongolian beef short ribs. The event drew some 550 guests and raised $2 million, which marks an increase over the $1.7 million raised in 2014. Next: October 2016

#8 Benefit
The 54th annual Golden Fellowship dinner returned to the Hilton Chicago this year. The evening’s program included a red carpet entrance and champagne reception, dinner, a performance from R&B singer Brandy, and an after-party. Comedian Damon Williams was the host, and the 1400 guests included well-known political figures such as Mayor Rahm Emanuel and Jesse Jackson. The evening's honorees were author Isabel Wilkerson and civil rights leader Timuel Black. Next year, the gala will celebrate the league's 100th anniversary. Next: November 2016

#9 Benefit
This year’s Columbian Ball raised more than $2 million for the Chicago museum. The night had robotic surprises (such as drones flying through cocktail hour), inspired by the "Robot Revolution" exhibition. There was also 1920s-style decor from Kehoe, and an after-party featuring DJ Questlove. Next: October 1, 2016

#10 Benefit
The benefit was founded by Rita Hayworth’s daughter, Princess Yasmin Aga Kahn, and each year, the it takes place at the Hilton Chicago during Mother’s Day weekend. In 2015, it raised more than $1.3 million and drew 865 guests; it also inspired a feature article in Michigan Avenue magazine. The evening featured entertainment from Orchestra 33’s Party Gras Band, as well as a cocktail reception, a three-course dinner, and auctions. Next: May 7, 2016

#11 Benefit
Some 900 guests attend the black-tie fund-raiser, which returned to Navy Pier’s Grand Ballroom this year. The event had an expansive silent auction, a dinner program with a live auction and a heart-tugging video, and an after-party dubbed “Ignite the Night.” It raked in $2.2 million. Next: April 9, 2016

#12 Benefit
Composer and lyricist Stephen Sondheim received the Carl Sandburg Literary Award at this year’s event. The gathering took place at the University of Illinois at Chicago, where organizers sat an author or artist at each table to interact with donors. The event drew nearly 700 guests and raised more than $1.5 million. Next: October 2016

#13 Benefit (new to the list)
Based in Israel, the Weizmann Institute of Science hosts an annual Chicago benefit that raises substantial funds for its scientists’ research efforts. This year, the event drew some 800 guests—including prominent business leaders and Mayor Rahm Emanuel—and raised a record-breaking $1.8 million. The evening featured an discussion on brain-related diseases between three of the institute’s scientists. Next: October 29, 2016

#14 Benefit
With an “Arctic Blast” theme, this year’s function had wintry decor from HMR Designs and Frost. The event, which drew more than 850 guests, raised around $1.1 million. The zoo’s carousel is left open for rides during the ball, and guests don animal-inspired black-tie garb. Next: July 15, 2016

#15 Benefit (up from #20)
This year, the event stayed on celestial theme with star-shaped butter on bread plates and a giant moon cutout that served as a photo backdrop. The ball raised $1.7 million for programming. Organizers connected guests to the cause by having local high school students perform science experiments at dinner tables. In recent years, the event has changed its format by adding a tent for cocktail and dessert receptions. Next: September 2016

#16 Benefit
Last year, the event celebrated the more than $2.7 million brought in by the Children’s Fund for the Lurie Children's Hospital throughout the year. This year’s black-tie event will have the theme: “Imagine! Bringing Possibilities to Life.” A return feature will be the “science fair for grown-ups,” where physician-researchers offer brief demonstrations during cocktail hour. Next: December 5, 2015

#17 Benefit (up from #18)
Popular with foodies and philanthropists alike, the winter benefit offers hors d’oeuvres prepared by top local chefs. It also includes the presentation of the Jean Banchet Awards for Culinary Excellence. This year, the event drew 900 guests and raised $500,000. Its theme was “Dubai—The Golden City.” Next year’s event will take place in a new venue: Navy Pier’s Grand Ballroom. Next: January 29, 2016

#18 Benefit (up from #21)
The 34th annual gala, titled “Wild Wild Whirl,” raised more than $1.2 million. During the cocktail hour, guests mingled with live animals, including a pink flamingo called Warren and an armadillo named B.J. Some 625 guests attended. Next: April 30, 2016

#19 Benefit (up from #24)
This year, the event (formerly known as the “Medicine Ball”) got a new name and took place at a new venue: the Radisson Blu Aqua Hotel. The program included cocktails, dinner, and dancing to a DJ. The evening raised a record-breaking $1.5 million (compared to $1 million in 2014) and drew some 400 guests. Next: Fall 2016

#20 Benefit
It is the sole fund-raising event for the volunteer board of Northwestern Memorial Hospital. With a “Magic of Prentice" theme underscored by actors dressed as fairy-tale characters, this year’s benefit took place at the Four Seasons Hotel. The 2015 affair drew some 400 guests and grossed nearly $1 million. The evening included a live auction with prizes such as a trip to Paris. Next: Fall 2016

#21 Benefit (up from #22)
For the 66th annual ball, 400 guests headed to the Grand Ballroom on Navy Pier. The night raised a record $1.4 million in support of local youth programs. The night featured decor by HMR Designs and live entertainment from the band Final Say. Next: May 20, 2016

#22 Benefit
The whimsical event always features an appearance by Ronald McDonald and has a kid-friendly theme. This year, the event was inspired by the big-top circus and featured popcorn-filled centerpieces, circus performers, and red-and-white striped decor. The night drew 800 guests and raised $540,000. The 2016 event will have a “Mission: Possible” theme. Next: March 5, 2016

#23 Benefit
More than 425 guests attended this year’s function on garden grounds. The elegant evening celebrated the 125th anniversary of the Chicago Horticultural Society, which helps maintain the garden, and it featured blue-and-white decor from Event Creative. The night raised $500,000. Next: June 2016

#24 Benefit
Benefiting the Chicago Gateway Green, this year’s event had a Studio 54 theme and took place at Venue One. The event features live DJs, casino games, and tastings from local restaurants. The bash—which drew 1,700 guests this year—is particularly popular among the young-philanthropist crowd. It raised $257,000. Next: September 2016