Tyler & Jenebib’s Luxury Private Yacht Wedding | Chicago, IL

Some weddings are beautiful — and others are unforgettable.
Tyler and Jenebib’s summer celebration on Lake Michigan was the perfect blend of elegance, spontaneity, and pure joy. What began as a fast-paced phone call in late May became one of the most breathtaking weddings I’ve ever had the privilege of designing.

Planned and produced by Graceful Weddings & Events in under two months, this celebration was a true masterclass in creative collaboration and trust. From the moment Tyler called and said, “Yep, it’s a green card wedding,” (to which I replied, “Perfect — we take every card, especially if it’s green!”) — I knew this couple was going to be special.

Hosted aboard a private luxury yacht cruising off Navy Pier and Lake Michigan, the event showcased the best of Chicago’s skyline at sunset. Guests enjoyed fine dining curated by Shaw’s Crab House, exquisite floral artistry by Juliet Tan Floral Design, and stunning photo + video coverage by WS Photography — who captured the city lights, fireworks, and the love between Tyler and Jenebib with absolute perfection.

The music and energy were brought to life by DJ Ron from Spinnin’ Discs, who also set up a photobooth and an old-fashioned rotary phone for guests to record messages to the couple. The bride’s timeless glam look was created by Pin Me Up Chicago, with Dana DiGiulio leading hair and makeup. Flourish Cake Design delivered a modern and elegant cake that perfectly matched the evening’s refined aesthetic.

The weekend began with an intimate rehearsal dinner at Chicago Cut Steakhouse, followed by a pre-wedding stay and brunch at Club Quarters Hotel, and wrapped with a wedding night at the LondonHouse Chicago, overlooking the same skyline that served as the evening’s backdrop.

Behind the scenes, Traci Kleinaitis and Devynn Kleinaitis from Graceful Weddings & Events worked seamlessly alongside our right-hand man Ricardo, ensuring every detail — from floral placement to dock coordination — was executed flawlessly. It was smooth, stress-free, and easily one of the best weddings I’ve ever been part of in Chicago.

Tyler and Jenebib never complained once. They never asked for anything more than one perfect shot — their guests with the entire Chicago skyline behind them. And they got it… along with so much more. The city sparkled. The boat rocked with laughter, music, and champagne. The fireworks lit up above us — and for a few perfect hours, it felt like all of Chicago was celebrating with them.

This wasn’t just a wedding. It was an experience.
A masterclass in trust, creativity, and pure love — planned with heart, humor, and a touch of skyline magic.