Panel discussions, Q&As and book signings were held during the one-day event in the West Loop.
Jenn Gibbons-Junk, who overcame an assault to row around Lake Michigan in 2012, was also one of the speakers.
Julie Foudy, a two-time FIFA Women's World Cup champion and former U.S. soccer team captain, even helped kick-start the day with a lakeside 5K.
Even Foudy, who translated her legendary soccer career into a successful sports journalism career at ESPN, said there are things she wishes women had shared with her as a young girl.
"I want women to be like 'Hey, maybe I don't know that skill set yet, but I'm going to raise my hand because the person next to me doesn't know either and they're raising their hand," Foudy said.
The Magazine and espnW Editor-in-Chief Alison Overholt, the first woman to hold the former title, wants her success to help the next generations stay focused.
"My biggest hope is that because I got to be the first, nobody else ever has to think about that again," Overholt said.
She also called Chicago "one of the greatest sports towns in the country," explaining that espnW wanted to capitalize on the sports marketing industry here.
USA volleyball star April Ross also discussed body image with a panel that included other Olympians.
"Strong is beautiful," the two-time medalist stressed after the panel, adding that kids shouldn't be worried about the body changes that come with intense physical activity. For her, the health and relationship benefits tied to sports will pay off.
Ross also said her sport has been at the forefront of gender equality on issues like equal pay and hopes other sports will look to volleyball as an example.
Conference attendee Stephanie Fallon appreciated the dialogue.
"You look at athletes and you think 'wow, they're in peak shape but they have insecurities too.' That's really relatable."