Theater on the Lake Wedding: Black, White, and Sparkle

Sally Jane and Shawn were married on a sunny autumn day at the iconic Theater on the Lake, surrounded by lakefront views, thoughtful details, and so much love. SJ first reached out to me looking for a wedding planner before she and Shawn were even engaged, and we hit it off immediately. Once they were officially engaged, they circled back — and from that moment on, it was all about intentionally designing a weekend that felt meaningful, joyful, and deeply personal for them and their guests. Read on to see more of their Theater on the Lake Wedding.

A Classic Chicago Rehearsal Dinner

SJ and Shawn kicked off their wedding weekend with a rehearsal dinner at Chicago’s iconic Gibson’s Steakhouse. Wanting an old-school Chicago feel, SJ leaned into deep red florals, rich décor, and specialty cocktails to set the tone for the evening. The dining room quickly filled with their nearest and dearest, and dinner began with the blessing of the challah (hamotzi).

This moment was especially meaningful, marking one of the couple’s first celebrations of their upcoming marriage and honoring Sally Jane’s recent conversion to Judaism. Shawn’s grandmother delivered a heartfelt toast, followed by his uncle bringing the room to laughter with his speech. The night ended late, with cocktails, conversation, and the kind of energy that only comes from being surrounded by your favorite people.

Welcome Weekend Festivities

Saturday was filled to the brim with wedding weekend events. The morning began with the couple and their families participating in a Jewish pre-wedding tradition called an Aufruf, celebrating the couple ahead of their marriage. That evening, all weekend guests gathered for casual welcome drinks at Old Town’s Benchmark. SJ and Shawn coordinated their outfits and looked effortlessly chic — the perfect preview of the celebrations still to come.

Wedding Day Begins

Wedding day arrived, and Sally Jane and Shawn started their mornings getting ready in separate hotel suites — SJ with her girls and glam squad, Shawn with his guys and a little bourbon.

Getting ready photos

After an emotional first look, Sally Jane took part in Kabbalat Panim, a Jewish tradition in which the bride gives and receives blessings from the important people in her life. At the same time, Shawn participated in a Tisch, where he was toasted and celebrated by his groomsmen. Soon after, the couple reunited and headed out for photos throughout the city before making their way to the venue.

A Meaningful Ketubah Signing

Once everyone arrived at Theater on the Lake, we moved into one of the most emotional moments of the weekend: the ketubah signing. Rabbi D’ror led the ceremony, and by the end, there truly wasn’t a dry eye in the room. SJ and Shawn’s faith is deeply important to them, and witnessing this moment was incredibly special.

Their ketubah was custom designed in the shape of a pomegranate — a symbol of fertility, abundance, and good deeds — and featured personal details woven throughout the artwork.

The Main Event

As guests arrived for the ceremony, they were greeted with a glass of bubbly and several instant wow moments: sweeping lakefront views, a dramatic 360-degree seating arrangement, and a 16-foot-tall chuppah adorned with hundreds of white flowers. The ceremony was stunning from start to finish, ending with the couple’s first kiss as newlyweds and a joyful exit through cold sparklers into cocktail hour.

Dinner, Dancing & Disco Balls

The reception kicked off with Sally Jane and Shawn’s entrance as Mr. and Mrs. Shapiro, set to You Are the Best Thing by Ray LaMontagne — a meaningful callback to their ceremony recessional. The groom’s mother, Tammy, welcomed guests with a heartfelt speech, followed by the bride’s and groom’s brothers blessing the challah and wine.

Throughout the evening, maids of honor and best men shared touching toasts, and the bride’s mothers closed out the speeches with a joint toast that tied the night together beautifully.

Then came the dancing. Under glowing disco balls, friends and family filled the dance floor for a night to remember — complete with an energetic Hora, of course. Afterward, SJ slipped away for an outfit change and returned just in time for a t-shirt toss hosted by the couple themselves. Coolest. Couple. Ever.

Every detail was infused with meaning, love, and celebration — a beautiful balance of tradition and modern elegance set against one of Chicago’s most iconic backdrops. Their day was a reminder of what happens when intention leads the way, and it was an absolute joy to witness the beginning of their marriage surrounded by so much warmth and community. Cheers to Sally Jane and Shawn!

Thank you to the event partner team for making this wonderful Theater on the Lake wedding possible:

• Planning: Your Day with EK
• Photography: Katy Carl Photography
• Videography: Fox + Ivory
• Content Creator: Hype Queen Media
• Musicians: Bluewater Kings Band
• Floral & decor: Flowers for Dreams
• Installations: Elegant Event Lighting
• Engraver: Meghan’s Mark
• Stationery: Elise Campbell Design
• Ceremony & reception venue: Theater on the Lake
• Catering: Blue Plate Chicago
• Glam: Cade Pearlman, The Bridal Collective, and Jenna Kantsedal
• Rehearsal dinner: Gibson’s Steakhouse
• Welcome drinks venue: Benchmark Chicago

Planning your wedding? Let’s chat!