Intentional wedding planning and design
company that specializes in weddings
that prioritize connection over perfection.

Intentional wedding planning and design company that specializes in weddings that prioritize connection over perfection.


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Sailboat Engagement Shoot in Chicago

May 17, 2023

We always strive to create unique and memorable experiences for our couples. Recently, we had the pleasure of organizing an enchanting engagement session for Lauren and Michael, which took place on a sailboat cruising the picturesque waters of Lake Michigan. With champagne flowing and a delectable mini charcuterie picnic, they enjoyed an evening aboard the Siren song.

When it comes to engagement sessions, we believe in showcasing the true essence of the couple and their chosen location. With the iconic skyline of Chicago and the vast expanse of Lake Michigan, we knew we had the perfect backdrop for Lauren and Michael’s love story. The sailboat provided an intimate and dreamy setting, adding a touch of elegance and a sense of adventure to their special day.

Boarding the sailboat, Lauren and Michael were greeted with champagne flutes, ready to toast to their future together. As the boat gracefully glided along the glistening waters, the couple savored every sip of their bubbly, reveling in the joy of the moment. The gentle breeze caressed their faces, creating a romantic ambiance that only added to the magic of the occasion.

Accompanying the champagne was a thoughtfully curated mini charcuterie picnic, designed to tantalize their taste buds. A delightful assortment of artisanal cheeses, cured meats, fresh fruits, and delectable treats awaited them, providing the perfect complement to their celebration. With each bite, Lauren and Michael indulged in the flavors while basking in the beauty of their surroundings.

Lake Michigan, with its shimmering waters and stunning skyline, served as an enchanting canvas for Lauren and Michael’s engagement session. The sailboat allowed us to create candid and breathtaking moments against the backdrop of the iconic Chicago skyline, creating timeless images that will forever encapsulate their love story.

As a Chicago wedding planner, it is our utmost priority to craft experiences that reflect the unique love story of each couple. From conceptualizing the idea to coordinating the logistics, we take pride in ensuring that every detail is meticulously planned and executed. For Lauren and Michael’s engagement session, we wanted to create a one-of-a-kind experience that truly captured their love and the beauty of Chicago.

Lauren and Michael’s sailboat engagement session on Lake Michigan was an unforgettable experience, filled with romance, elegance, and breathtaking views of Chicago’s skyline. As a Chicago wedding planner, we were honored to be a part of their journey and create a truly magical moment for them. The combination of champagne, a mini charcuterie picnic, and the serenity of sailing on Lake Michigan made their engagement session an occasion that will forever hold a special place in their hearts. If you’re looking to capture the essence of Chicago in your engagement session or wedding, consider the charm and expertise of a Chicago wedding planner who can turn your dreams into a reality.

Vendor Team:
Planning/Design: Jeannene Lillie Events | Photography: Kelly Sweet Photography

Jeannene Lillie is a Michigan Wedding Planner and Michigan Event Planner serving clients in Michigan, Pittsburgh, Ohio, San Diego, and Worldwide Destinations. The JLE Team is committed to coordinating and designing inclusive and intentional events that celebrate the romantic and modern couple. Inquire with us today and stop by the JLE Instagram to get a peek into our beautiful events and get to know us better!

Michigan Wedding Planner | Pittsburgh Wedding Planner | Ohio Wedding Planner | San Diego Wedding Planner | Chicago Wedding Planner

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the woman behind the clipboard

MEET jeannene

Romantic, passionate hostess, wife, sentimentalist, inspired by connection, and your love story.

Jeannene is the owner and creative director of JLE. For as long as she can remember, Jeannene has always been the friend bringing her people together to celebrate life's little and big moments.

It is a deep belief of hers that gathering is one of the most sacred things we do as a culture and she brings that energy towards every celebration and environment that she is called to create.

Intentionally bringing people together in a one of a kind atmosphere is her passion, and she cannot wait to share that with you on your wedding day. 


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