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Women of the Year leader
Bryan Mayes

8 women who are making Chicago a better place this year

Meet Time Out Chicago's amazing Women of the Year, who are each giving the city something to talk about.

Zach Long
Written by
Zach Long

In honor of Women's History Month, we're celebrating artists, activists, entrepreneurs and community leaders who are helping make Chicago's future brighter.

Throughout the past year, these women made contributions to the city that took many different forms, from running organizations that lend assistance marginalized groups to creating music with an empowering message. Just like Chicago's women-owned businesses, each of these women has made the best of an incredibly tough year, sharing their talents and knoweldge with their communities.

We caught up with each of Time Out Chicago's Women of the Year to learn more about their work, their plans for coming year and on-the-rise women in their own fields that they think we should be paying more attention to.

Written by Zach Long and Morgan Olsen.

Time Out Chicago Women of the Year 2021

LaSaia Wade

When protesters took to the streets of Chicago last summer in response to the police killings of Black people like George Floyd and Breonna Taylor, Brave Space Alliance executive director LaSaia Wade sprang into action. “I knew it was our job to stop what we’re doing and figure out how to support people on the ground,” she says, describing how Brave Space Alliance provided food and clothing to protestors, opening up their offices as a safe space.

Wade founded the South Side’s first Black-led, trans-led LGBTQ+ center in 2017, after being rejected from countless jobs. She realized that, as a Black trans woman, she was searching for a place where she felt fully accepted. “There wasn’t a place where trans people could say, ‘That’s my beacon,’ but there’s a lot of places for lesbians and gay cis men,” Wade said. 

Over the past year, Wade has overseen a flood of support, multiplying the organization’s budget from $300,000 to $3.5 million. That money has funded the purchase of Brave Space Alliance’s Hyde Park headquarters and a slew of resources, including a food pantry, a mutual aid program and a telehealth program—all focused on supporting BIPOC trans and gender-nonconforming individuals. “If an organization is supposed to do organizational work, you’re actually doing the work of putting yourself out of business,” Wade said, stressing that the ultimate goal of Brave Space Alliance is to make its existence unnecessary.

Support the mission of Brave Space Alliance by making a monetary or material donation.

A Q&A with LaSaia Wade

What Brave Space Alliance program do you feel has had the biggest impact over the past year?
“The one that hit is the first LGBT pantry in the Midwest. We service over 300,000 people in nine months and we still are.”

What is your primary goal for Brave Space Alliance in the coming year?
“We’re buying two houses for homeless trans and gender-nonconforming people. My goal this year is to open our housing program.”

What organizer has served as a source of inspiration for you?
“There’s a leader I’m always talking to and she’s my gay mother, Valerie Spencer. She’s a woman who has taught me what it looks like to thrive as a trans woman but also to push myself a bit farther.”

What’s the best way to support or get involved with Brave Space Alliance?
“Look at your own capacity. If you can only donate, do that. If you can volunteer, do that. We accept all types and levels of time, currency and volunteers.”

Who is the up-and-coming woman in your field we should all be looking out for?
“Kayla Gore, she created Tiny Homes for Trans Women of Color.”

Diana Dávila

Last summer, acclaimed Logan Square restaurant Mi Tocaya Antojería dished out thousands of free meals to Chicago families in need. Chef-owner Diana Dávila was so fulfilled by the experience that she recently launched her own followup project that’s designed to not only provide free meals to the community but also support undocumented restaurant workers and local farmers. 

With help from local nonprofits Dishroulette Kitchen and the Logan Square Neighborhood Association, Todos Ponen allows Mi Tocaya to keep its doors open and shine a light on the unique struggles of the city’s undocumented workforce. “Throughout this whole process, it’s been incredibly scary for undocumented workers, Dávila says. “Many of them don’t have the choice to stay at home and not work.” To help drum up donations to fuel the project, Dávila hosts intimate interviews with top Chicago chefs (including Virtue’s Erick Williams and Thattu’s Margaret Pak); you can find and watch them on Mi Tocaya’s Instagram page.

Help Dávila and her team feed the community and support undocumented restaurant workers when you donate to Todos Ponen. 

A Q&A with Diana Dávila

Name a Chicago restaurant more people should be shouting about.
Luella’s Southern Kitchen. I know they already have a big following, but it was a game-changer for me. The best collard greens, the best fried chicken—we order everything on the menu.”

Where do you find inspiration in Chicago?
“Through people. That’s what hospitality is. Making eye contact and taking the time to listen is so important.”

What’s one piece of advice you’d give to diners right now?
“Have patience.”

What’s one way restaurants will change forever post-pandemic?
“The tip structure. We changed our structure so that everyone makes the same amount of money and tips are shared. I wish I would have done this even sooner.”

Who is the up-and-coming woman in your field we should all be looking out for? “Jhoana Ruiz, the chef of Santa Masa Tamaleria. I am very excited to see what she does with the menu.”


Jiayan “Jenny” Shi

When Chinese student Yingying Zhang disappeared from the campus of University of Illinois at Urbana-Champaign in 2017, the tragic story caught the attention of people all around the world. Jiayan “Jenny” Shi felt a personal connection—just like Zhang, she came to the United States as a student, studying journalism at Northwestern University’s Medill School. As part of a call during her final quarter, she picked up a camera for the first time and began working on a documentary about Zhang’s murder. “I started to realize the power of longform storytelling,” Shi said. “Being a documentary filmmaker really allowed me to experience other peoples’ lives.”

It took more than two years for Shi to finish her debut documentary, Finding Yingying, during which time she met Zhang’s family and became a fellow at Chicago-based Kartemquin Films. Telling the story of Zhang’s disappearance and the trial of her killer, Finding Yingying debuted at various virtual films festivals last year, won the Chinese Academy Award for Best Foreign Language Documentary and was acquired by MTV Documentary Films. On the heels of her success, Shi is already working on a new documentary, exploring the Chinese American experience in the U.S. and women’s rights in China. 

Learn about how you can watch Finding Yingying.

A Q&A with Jiayan “Jenny” Shi

What’s your favorite place to see a movie in Chicago?
AMC River East 21, I went to the Chicago International Film Festival there two years ago.”

What’s your favorite Kartemquin Film?
Minding The Gap, I just really love it and I cry every time I watch it.”

What’s the most powerful documentary you’ve seen recently?
Last Train Home, it’s a documentary that’s about a Chinese couple that work in a factory and their relationship with their child who they left behind in rural China. It’s a very intimate family portrait about working class life in China.”

Where do you go when you’re feeling homesick in Chicago?
“I live in Evanston, so I go to the lake near the Northwestern campus and just enjoy the view of the city.”

Who is the up-and-coming woman in your field we should all be looking out for?
“Ashley O’Shay, the director of Unapologetic, another Kartemquin Film.”

Rossana Rodriguez Sanchez

Despite the fact that she grew up with a father who was a community organizer, Rossana Rodriguez Sanchez didn’t initially see herself becoming involved with electoral politics. But after working on Tim Meegan’s 2015 campaign for 33rd Ward Alderman—which he narrowly lost to politically-connected incumbent Deb Mell—Rodriguez Sanchez changed her mind. Inspired by Bernie Sanders’ 2016 campaign, she ran for 33rd Ward Alderwoman in 2019 as a Democratic Socialist, espousing the representation and protection of undocumented immigrants in her community—and she won.

Since taking office, Rodriguez Sanchez has stuck to her progressive agenda, recently helping pass a revised version of Chicago’s Welcoming City ordinance that eliminated all exemptions allowing Chicago Police to cooperate with Immigration and Customs Enforcement agents. She’s also fighting to protect tennants through a “Just Cause for Eviction” ordinance and introduced an order last September called “Treatment Not Trauma,” that would establish a model for mental health emergency response that doesn’t involve police.

A longtime Albany Park resident who has experience working with undocumented youth, Rodriguez Sanchez is still fighting to keep her ward a welcoming place for all. “Whoever is in this seat needs to be absolutely committed to affordability in our neighborhood and protecting undocumented immigrants,” she said. She doesn’t bristle at comparisons to fellow Democratic Socialist Alexandria Ocasio-Cortez—Rodriguez Sanchez has considered herself a socialist for much of her life and sees her position as a way to continue the movement’s work. “It’s a really big opportunity to advance socialist ideas, to talk about them, make them popular and break the stigma,” she said.

A Q&A with Rossana Rodriguez Sanchez

What do you feel is the most important issue Chicago needs to address right now?
“I think the biggest issue in Chicago right now is the overuse of police to address every issue that we have in this city. We need police reform and to shift resources that we’re spening on policing and put it into social services like mental health.”

What’s the best way to get involved with the DSA?
“DSA has a lots of events for new members and there’s also many working groups. If people go to social media or the DSA Chicago website, you can see when the new member orientations are and get connected with whatever group speaks to you.”

Who is one national politician that gives you hope for the future?
“Cori Bush is a new force in Congress and she inspires me a lot. She was such a huge part of organizing against police brutality and racist police violence, and has taken that voice on Congress and continues to push for justice.”

What’s one place in the 33rd Ward that every Chicagoan should visit?
“Albany Park is a magical place and I think everyone should come here, walk around and eat in lots of restaurants from different parts of the world.”

Who is the up-and-coming woman in your field we should all be looking out for?
“Delia Ramirez, she’s an Illinois State Representative, she is an incredible fighter currently doing all that she can to make sure that there is affordable housing and that people are protected. She’s an unapologetic fighter and I love and respect her so much”


Maggie Winters

A bit of levity has gone a long way over the past year, and if you follow enough Chicagoans on Twitter, you’ve probably had the pleasure of chuckling while watching a video by local comedian Maggie Winters. Whether she’s portraying a Midwestern mom trying edibles for the first time, a Chicago dad who loves indie rock bands or a heightened version of herself, Winters’ characters are at once endearing and absurd.

A veteran of the Chicago improv scene, Winters was performing multiple nights a week at iO Theater and the Annoyance Theatre before the pandemic put the kibosh on live shows. The Beverly native turned to Twitter as a way to encourage herself to write while in quarantine, inspired by the success of tweets and videos created by contemporaries like Caleb Hearon and Grace Kuhlenschmidt.

“The videos were just something that made me step out of my comfort zone and try to be a little more creative,” Winters said, explaining how she films whenever inspiration strikes, sometimes collaborating with her brother Liam (bassist for local rockers Melkbelly) on ideas and scripts.

Thus far, videos like “being fat online” and “thanks siri” have garnered thousands of likes and retweets, and led to invitations for Winters to appear on various comedy podcasts and streaming shows. Winters hopes to return to the stage when comedy theaters eventually reopen, but she also has ambitions to work as an actor and writer—she hasn’t landed an agent yet, but with her viral creations being seen by more and more people, it only seems like a matter of time.

Follow Maggie Winters on Twitter and TikTok.

A Q&A with Maggie Winters

What Chicago comedy institution have you missed most over the past year?
“CIC Theatre, it’s a black box theaters and it’s the first place that put me on a team.”

What Chicago stereotype is the easiest to make fun of?
“The easiest is our food choices. I’m a big fan of deep dish pizza so I get heated defending it.”

What comedian consistently makes you laugh?
“I love Grace Kulenschimt, she’s huge on Twitter and I feel like she’s going to take over the world.”

What the most exciting retweet you've recieved?
“Natasha Lyonne retweeted me and I freaked out.”

Who is the up-and-coming woman in your field we should all be looking out for?
“Jordan Lee Cohen, she ran the Holy Fuck Comedy hour at Annoyance Theatre.”

Eva Maria Lewis

Shortly after the killing of Trayvon Martin in 2012, Eva Maria Lewis attended her first protest on Michigan Avenue with her mother and was introduced to activism as a conduit for change. “For so many people in my generation, their realities were disrupted by what happened to Treyvon Martin,” Lewis said. “We had been taught that violent racism ended with the Civil Rights movement, but that wasn’t the case.”

Lewis founded the organization that would eventually become Free Root Operation when she was just 16, as she began to think of ways to combat the gun violence plaguing her community and expand the resources available to residents. When she was a senior in high school, she came up with the idea for a pair of “peace rooms” at Bouchet Elementary, providing a safe alternative to the principal's office and after-school detentions.

Free Root Operation was relaunched last summer in response to the uprising surrounding the police killings of George Floyd and Breonna Taylor, as grocery stores on Chicago’s South and West Side shut down in anticipation of unrest. Lewis organized a food pairing program, enlisting volunteers to shop on the North Side and deliver customized grocery orders to more than 500 families.

Working with a small team of Free Root Operation collaborators, Lewis remains committed to helping empower her community through the work of her organization. “We want to show people that we can build our communities up,” Lewis said. “We don’t have to mirror other communities or wait for the government to service us when they’ve shown us time and time again they won’t.”

Make a donation or sign up to volunteer with Free Root Operation.

A Q&A with Eva Maria Lewis

Who has served as a source of inspiration for you?
“My mentor Brittany Packnett Cunningham really inspires me all the time and tells me what I’m doing is possible.”

What is your primary goal for Free Root Operation in the coming year?
“To expand our constituent base and get people on board with the idea that we can create. We really want to get people involved in the conversation about what it looks like for Black and brown sustainable communities to exist that meet all of our needs.”

What’s the best way to support or get involved with Free Root Operation?
“Sign up for our newsletter, donate online or sign up for our Rooted in Freedom club—it’s basically our volunteer database.”

What's the simplest way for someone to start helping folks in their own community?
“I think the first thing is to ask people what they need. The goal should be to empower—there are a lot of people who try to invoke change by asserting their agenda upon others, but the goal is to help people reach their own agendas.”

Who is the up-and-coming woman in your field we should be looking out for?
“Nita Tennyson, she has an organization called Nita’s Love Train and she has tables of baby supplies and household supplies that people can come and get.”


Lili Trifilio

When Lili Trifilio began writing songs in her bedroom while studying at DePaul University, Beach Bunny was a self-recorded solo project. By the time, she graduated in 2019, Tifilio had a full-fledged band, a body-positive pop-punk anthem that became a viral TikTok sensation (“Prom Queen”) and a contract with New York independent label Mom + Pop Records—the home of artists like Courtney Barnett and Sleater-Kinney.

Trifilo’s plans to tour behind Beach Bunny’s debut album, Honeymoon, were derailed by the pandemic, as venues across the country closed their doors. But the time away from the road gave way to a new solo project (called Tiger Lili) and Beach Bunny’s Blame Game EP, built around a quartet of songs that frankly address sexism, gaslighting and the objectification of women. 

“I think in general with songwriting, I wear my emotions on my sleeve a bit,” Trifilio said.  “When I was writing Blame Game I was going through this angry period in my life and I had a lot of time to reflect—it brought up a lot of frustrated emotions from the past.”

While she waits for touring to resume, Tifilio and her band are already hard at work on Beach Bunny’s sophomore album, which she hopes to debut before the end of 2021. “It’s more about accomplishing it without rushing it,” Trifilo said about the group’s next release, making it clear that if the past year has taught her anything, it’s that having an abundance of time can be a valuable creative asset.

Listen to and purchase Beach Bunny's music.

A Q&A with Lili Trifilio

What’s the best way to support local musicians right now?
“Purchasing physical copies of their music.”

What local venue do you miss performing at the most?
“It’s gotta be split between Thalia Hall and Subterranean—it always feels like home.”

What’s the one thing you miss the most about touring?
“Just seeing people that are listening to the music.”

Who is your dream collaborator?
“I don’t think it would make sense for Beach Bunny, but probably Grimes or Charli XCX.”

Who is the up-and-coming woman in your field we should all be looking out for?
“Kathy Patino and her project Girl K, she’s a super, super sweet chick.”

Rohini Dey

Back in March 2020, Rohini Dey closed the doors to her River North restaurant and wondered what would happen next. For four months, the bills piled up and she couldn’t help but worry. It wasn’t until July that she was able to safely reopen Vermilion at a limited capacity. But even then, she had questions and concerns. So she phoned a handful of other local women restaurant owners to check in and see how they were faring. They exchanged tips on testing staff, air-purification systems, patio furniture and plexiglass dividers. But more than anything, they bonded over a shared experience. 

“Then I realized that we were being so helpful to each other that wouldn’t this be wonderful in other cities too?” Dey says. “So I just started reaching out to friends. Everyone instantly said yes.” Let’s Talk was born and has since expanded to 12 cities—from Atlanta and Boston to San Francisco and Seattle. Harnessing the power of 350 women restaurant owners, the group activates virtual events and explores topics like bargaining power, political action and coping with crisis. Their work is far from over, even now that the end of the pandemic is in sight. “We want to continue using this group to amplify our voice,” Dey says. “Whether it’s vendors, visibility or accessing policy makers.”

Help Dey and women restaurateurs in 12 cities across the U.S. continue connecting and building experiences when you donate to Let’s Talk Womxn

A Q&A with Rohini Dey

What’s your go-to takeout order at the moment?
“My last really good meal was Greek from Taxim. I also always enjoy ordering from Frontera and neighborhood spots, like Pizza Capri.”

What’s the easiest way to support Chicago restaurants right now?
“Dine out and continue doing takeout—at the end of the day, we have to survive to make it. Write a review or share your experience with your network.”

What’s your proudest moment from the past year?
“Our International Women’s Day dinners were euphoria. We had amazing conversations in nine cities. It was so great to see it come to life.”

What’s one way restaurants will change forever post-pandemic?
“Putting employees first has catapulted to the top of our minds. We won’t sacrifice our employees at the altar of commerce.”

Who is the up-and-coming woman in your field we should all be looking out for?
“Geri Guidote [of Savory Crust], for her ability to tackle adversity with infectious and unbounded zeal and her incredible ‘real-food’ fare.”

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