Thursday, May 14, 2026
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The Working Lunch Raffle
PLATINUM PLUS PACKAGE ($250 purchase):
"Broaden Your Horizons"
Be your best self with this package. Elevate your professional life with a 90-minute Brand and Marketing Power Session, including a recording, notes, and recommendations with DesignScout, a strategic branding studio with over 20 years of experience. Look and feel your best with an Essential Headshot/Portrait Session with Kambua Chema Photography. And don’t forget leisure time—relax with a two-night hotel stay, dinner, and spa experience at a destination that Chicago Magazine named one of Chicagoland’s top seven staycation spots. Finally, take a trip anywhere Southwest Airlines flies with two international, round-trip tickets.
*subject to distance and schedule limitations
PLATINUM PACKAGES ($100 purchase):
Platinum Package 1: "Enrich Yourself"
Spruce up your life with some fun and enriching activities at home or away! You can find yourself at the Chicago Architecture Center for a walking tour for four or on a nice trip with an international, round-trip ticket from Southwest Airlines. Staying in? You could also settle down with your friends for an incredible wine tasting for up to twelve at home with PRP Wine International. After the wine, enjoy a private, 30-minute performance by professional opera singer Elizabeth Novella.
Platinum Package 2: "Fun Going Out and Fun Staying In"
Enjoy your life whether you go out or stay in. For going out, you’ll have two tickets from the Chicago Shakespeare Theater for your choice of shows in the 2026 season! On top of that, there are four tickets to see women-led band Evanescence in concert on July 8 thanks to Live Nation. And go out wherever you’d like with an international, round-trip ticket from Southwest Airlines. If you want to enjoy yourself staying in, you have an incredible at-home wine tasting with PRP Wine International for up to 12 people!
DELUXE PACKAGES ($25 purchase):
Deluxe Package 1: "Support Local"
Embrace your local community in Chicago. Buy some flowers for a loved one (or yourself! Why not?) with a $65 gift certificate from Flowers for Dreams. Get out and explore at the Field Museum with four entry passes, watch a Chicago Stars FC game with four tickets, then relax at Revolution Brewery with some merchandise and a $50 gift card.
Deluxe Package 2: "Self Care"
Self care of all kinds is important! First, find fun new ways to move your body with a free class and week membership at Brooklyn Boulders and one week unlimited class-pass at AIR Aerial Fitness. And because there are many forms of self care, indulge in some natural beauty and home products with a $50 gift card from the Merz Family of Brands. Finally, take care of your skin with the four-piece Caire Beauty set, provided by Gifting Brands.
Deluxe Package 3: "Getting Sporty"
This is the perfect package for sports lovers—both playing and watching! Grab three fellow sports fans and check out the White Sox playing with four free tickets! Keep the fun going with four club-level tickets (valued at $50 each!) to see the Chicago Fire FC. Are you hoping to be on the field one day, or at least inspired by watching all that athletic performance? Take advantage of all Chicago Athletics Clubs has to offer with a two-month All-Access Membership!
$25 for 1 Deluxe entry • $50 for 3 Deluxe entries • $75 for 6 Deluxe entries • $100 for 1 Platinum entry + 5 Deluxe entries • $250 for 1 Platinum Plus entry + 1 Platinum + 10 Deluxe entries
Raffle tickets support Women Employed’s work to create a better economic future for women. Raffle sales will close at 5:00 p.m. on Thursday, May 14th, 2026. Winner need not attend the The Working Lunch to win. A WE staff member will reach out to winners directly by email to coordinate prize mailing or pickup.
MEET OUR 2026 HONOREES
At The Working Lunch, we will honor and celebrate leaders who have harnessed their own power to defend our progress, ensure working women know their rights, and advance change so women, families, and communities can thrive. Learn more about our Trailblazer and Champion honorees!
SPECIAL GUEST
Whitney Reynolds believes in creating more seats at the table, finding inspiration in the hardest moments, and spreading hope for all. That philosophy shaped the Whitney Reynolds Show, which launched in 2012 on PBS with a mission that went against the grain—offering a safe space for real, often harrowing stories that uplift and connect.
Drawing from her own challenging childhood, Whitney combined personal resilience with her “gift of gab” to craft a program that flips the script—inviting viewers to feel seen for who they are and where they’ve been.
Today, she serves as Executive Producer, Host, and “Chief Inspo Officer” of the Telly Award-winning and two-time Emmy®-nominated Whitney Reynolds Show. Taped in Chicago at CineCity Studios, the show is nationally syndicated on PBS via NETA, airs coast to coast on PBS’ World Channel, and streams on Prime Video, Tubi, the PBS App, Roku and beyond. Before launching her nationally syndicated program, Whitney worked in news for NBC and created her first talk show on that network. She is a Crain’s 40 Under 40 honoree and recipient of the Stevie Award for “Equality in Pay for Women.”