
#1 Benefit (up from #2)
While the 2016 benefit pulled in $2.4 million, this year’s event raised an impressive $6 million. Held for the first time at the Field Museum, the ball drew 1,100 guests—as opposed to 750 in 2016. The event draws strong corporate support, and Boeing Company was the presenting sponsor this year. Notable attendees included Mayor Rahm Emanuel, and The Late, Late Show host James Corden was the M.C. Next: Spring 2018

#2 Benefit
Held at the new Wintrust Arena, the 2017 benefit drew nearly 1,000 guests and featured speeches from Mayor Rahm Emanuel and After School Matters board chair Mellody Hobson. The evening supports programs for local teens, and the gala showcased a gallery of student artwork and offered performances from the program’s participants. The event raised more than $4 million. Next: Fall 2018

#3 Benefit (up from #9)
Held in Navy Pier’s Grand Ballroom, this year’s gala raised $3.3 million dollars, a significant increase over the $2 million raised in 2016. The event also drew 1,100 guests; in 2016, 900 guests attended. After the gala, an after-party struck up on the venue’s lakeside terrace. Next: Spring 2018

#4 Benefit
The 2016 gala raised $4.9 million, which marked an increase from the $4.2 million raised in 2015; some 1,900 guests attended. The gala is known for an expansive silent auction that features hundreds of packages each year. Next: December 9, 2017

#5 Benefit
The 2017 gala once again took place at Navy Pier. Actor John Stamos was the emcee, and the night drew 969 guests and raised $2.4 million. Next: Spring 2018

#6 Benefit (up from #7)
The 2016 gala honored the museum’s women’s board on its 50th anniversary. Since the event coincided with the 2016 World Series—which the Chicago Cubs would go on to win—planners arranged for a viewing of the game. This year, the gala had an Ancient Mediterranean Cultures in Contact theme and raised $2.2 million. Next: Fall 2018

#7 Benefit (up from #10)
The iconic Diana Ross performed at the 2016 dinner. Other highlights included the presentation of the newly created individual service award. The event raised a record-breaking $2.65 million and drew some 1,700 guests. Next: November 4, 2017

#8 Benefit
With butterflies aplenty in its decor, the springy gala raised $2.15 million this year and drew 650 guests. The evening allowed guests to walk through the museum’s butterfly house and interact with turtles; there was also dinner and dancing. Next: Spring 2018

#9 Benefit
Dubbed “Voyages,” this year’s event was inspired by travel. The evening drew 750 guests—as opposed to 700 in 2016—and raised $1.9 million. The gala featured a refreshed format: The after-dinner dancing moved indoors, and guests could also kick back in a pop-up jazz lounge after dinner. Next: Spring 2018

#10 Benefit
Along with cocktails, dinner, and dancing, the annual gala offers guests the opportunity to explore the museum after-hours. This year, gala-goers checked out the exhibits “Robot Revolution” and “Brick by Brick.” The event raised more than $2 million for the museum. Next: Fall 2018

#11 Benefit
Held once again at the Hilton Chicago, the glitzy fund-raiser drew more than 800 guests and raised $1.1 million. The event featured a cocktail reception with live violinists, as well as a three-course dinner and a chance for guests to applaud scientists and researchers working on Alzheimer’s research. Next: Spring 2018

#12 Benefit
Authors Margaret Atwood and Dave Eggers were honored at this year’s function, which took place at the Forum at the University of Illinois at Chicago. Seventy writers with Chicago ties also attended the event, each seated at a table to engage in literary discussions with guests. The event drew 830 guests and raised $1.8 million. Next: Fall 2018

#13 Benefit (up from #14)
Dubbed “The Mane Event,” this year’s safari-theme bash celebrated the 40th anniversary of the zoo’s women’s board. The evening drew 850 guests and raked in $1.4 million. Highlights included staff dressed as safari guides, and African-inspired decor by Erin McDonald Co. Next: Summer 2018

#14 Benefit (up from #15)
The women’s board of the planetarium hosts the late-summer event, which raised more than $1.5 million in 2017. Some 600 guests donned black-tie attire for an evening of cocktails, dinner, and tableside science demos from local students. Next: September 2018

#15 Benefit
The Israel-based Weizmann Institute of Science hosts an annual Chicago benefit to support its research programs. In 2016, the evening honored civic leader and philanthropist Renee Crown. It drew 400 guests and raised $965,000. Next: October 28, 2017

#16 Benefit
During cocktail hour, guests are treated to “animal encounters.” This year, an owl and a miniature fox interacted with party-goers. To celebrate the 25th anniversary of the zoo’s women’s board, Kehoe Designs brought in all-white, diamond-theme decor. The event raised $1.2 million and drew 620 guests. Next: April 28, 2018

#17 Benefit
In 2016, the end-of-year benefit returned to the Hilton Chicago. The evening included cocktails, dinner, and live entertainment; there was also a moving video presentation highlighting the work of Ann & Robert H. Lurie Children’s Hospital of Chicago. The evening celebrated the $2.5 million brought in by the Children’s Fund throughout the year. Next: December 2, 2017

#18 Benefit
The 2017 gala marked the 20th anniversary of the food-centric event. Some 900 guests attended, tasting small plates from a variety of local chefs. An unusual dinner menu featured fried leeks and venison; there was also an after-party with pastries and craft cocktails. The event raised more than $670,000, which marks an increase over the $400,000 raised in 2016. Next: February 2, 2018

#19 Benefit (up from #21)
The 10th annual event drew some 500 guests, and raised more than $1 million. Held at the Geraghty, the festive evening included a seated dinner, a live auction, and entertainment. Next: Spring 2018

#20 Benefit (up from #22)
Some 700 guests turned out for this year’s gala, which celebrated the host’s 40th anniversary. By comparison, 650 guests attended in 2016. This year’s event also raised significantly more money, bringing in $945,000 as opposed to $500,000 in 2016. The event featured an appearance from Ronald McDonald, and guests were treated to McDonald’s Arctic Orange Shakes and cheeseburgers at the after-party. Next: Spring 2018

#21 Benefit
This year’s event took place at the Radisson Blu Aqua Hotel and was dubbed “The Wonder Ball.” The evening drew 350 guests and raked in $2 million, which was more than the 2016 take of $1.7 million. Next: Spring 2018

#22 Benefit
The 2016 event had a “Passport to Prentice” theme, and took place at the Four Seasons Hotel Chicago. This year’s function moved to the Radisson Blu Aqua Hotel, and had a “Remember When” theme. The event typically raises around $1 million. Next: Fall 2018

#23 Benefit
With a Brazilian theme, this year’s event offered cocktails, dinner, and dancing in a tent filled with colorful decor by Kehoe Designs. After a dinner of chilled avocado soup and petit filet, a samba band took to the stage. The event drew 450 guests this year—as opposed to 300 in 2017. And, it raised quite a bit more of money this year: The 2017 take was $900,000, while the 2016 take was $350,000. Next: Spring 2018

#24 Benefit
This year’s sold-out benefit drew 1,000 guests and raised $300,000. Celebrity guests included actor Taylor Kinney, who auctioned off a hug and a signed helmet from the set of Chicago Fire during the live auction. The event also featured tastings from local restaurants, entertainment on several stages, and an indoor-outdoor setup. Next: Summer 2018