When classic taste meets bespoke design, you get a wedding like this one. With a sense of place that could only be vibrant downtown Chicago, it was one of our favorite celebrations from last year. Our couple, Toyia and Dennis, gave us complete creative freedom to bring their vision to life. From the rehearsal dinner at Taste 222 to the vow exchange and reception at the Midland Hotel, it was an unforgettable weekend executed by a team of majority Black-owned vendors.

Flatlay of a black and white wedding invitation by DEJAMAKES Creative Studio

Flatlay of cream roses, and silver Paradox London heels

Bride in a white robe looking out the window of her hotel room

Bride getting ready for her wedding at the Midland Hotel

Groom getting ready for his wedding at the Midland Hotel

Groom's wedding party portraits in Downtown Chicago

First look in front of a historic building in Downtown Chicago

Bride and groom laughing after their first look

Bride and groom reading private wedding vows

Wedding party portraits in Downtown Chicago

Bridesmaids wearing dark green dresses and holding calla lily bouquets

A Sophisticated Wedding with 1920s Flair

Classic Chicago style was at the core of Toyia and Dennis’s wedding-day vision. Our search for the perfect venue led us to the Midland Hotel, where the couple fell in love with the timeless architecture and location in the heart of the city. With sparkling chandeliers and lofty ceilings, the hotel evokes the Chicago of the past, a concept that became our guiding star in designing this wedding.

The reception space reflected the building’s former use as an early twentieth-century social club. Moody lighting and a mix of round and rectangular tables created an intimate dining atmosphere, while touches of custom decor anchored the setting firmly in Toyia and Dennis’s story. Black and white details exuded sophistication without seeming old-fashioned—the houndstooth napkins and checkered dance floor were proof that a timeless palette is anything but boring.

1920s speakeasies inspired our designs for the bar and lounge. A vinyl wrap featuring the couple’s initials and an Art Deco pattern elevated the standard bar into a stand-out piece of decor, while custom signage advertised signature cocktails. In the nearby lounge—featuring plush green velvet couches and custom pillows—guests could peruse leather-bound menus to find their drink of choice, or indulge in a hand-rolled cigar from Don Alejandro’s.

Bride and groom holding hands and walking across the street

Groom wearing an ivory tuxedo and a black silk bowtie

Bride and groom embracing underneath her veil

Event Shoppe Chicago - Chicago Wedding Planner

Bride and groom exchanging vows in front of a white fireplace with cream roses

Bride and groom walking down the aisle after their Chicago wedding ceremony

Reception at the Midland Hotel

Toyia and Dennis’s reception was true to them from start to finish. After greeting their guests, who each received a thank-you note from the couple at their place setting, they changed outfits for the first dance. Dennis swapped his white suit jacket for a dark green one with black lapels, while Toyia donned a flirty knee-length dress with a tiered tulle skirt. Their choreographed dance to a medley of Prince songs was a huge hit, especially when Dennis pulled out his guitar.

Then, as Simone Green swept onstage to kick the dance party off, the newlyweds snuck away briefly for a special photoshoot. Dennis is an antique car enthusiast who owns a 1960s emerald green Mercedes—a.k.a., the perfect prop for bridal portraits outside a historic hotel. With cigars in hand, the couple posed in the backseat and against the hood, soaking up every minute of their special night (and looking damn good doing it!).

Aerial view of tables with dark green tablecloths at a Chicago wedding

Black and white accents at a Chicago wedding

Bar with a custom vinyl wrap at a Chicago wedding

Bride and groom cutting a black and white wedding cake

Bride and groom kissing during dinner at their wedding reception

Bride and groom sharing their first dance on a checkered dance floor

Defined by feel-good moments and impeccable styling, this wedding at the Midland Hotel was the kind that sticks with you long after the lights have gone out and the cake has been eaten. We’re so grateful to Toyia and Dennis for the trust they placed in us. If you’re dreaming of a Chicago wedding that shatters the status quo, you’ve come to the right place! Our team would love to help you design a celebration that shares your love story, in all its unique glory. Contact us to get started.

Wedding cigar bar by Don Alejandro's Finest Cigars

J Lauryn Photography - Chicago Wedding Photographer

Bride and groom holding cigars and posing in front of an antique car

Kind Words from Toyia and Dennis

“We wanted to find a partner who would connect with us culturally to create the perfect wedding—one that showcased not only who we are as a couple, but also the richness and beauty of Chicago’s history. Within five minutes of our first meeting with Jennifer, we knew we had found the perfect person to do this. Neither one of us is very detail-oriented or organized, so Jennifer immediately held our hand through the entire process, keeping us sane and updated without ever overwhelming us. When we walked into the reception, our mouths dropped wide open—we were blown away. It was absolutely beautiful, everything we wanted: classic, timeless, and like walking into a Chicago social club. We truly feel that with Jennifer and Event Shoppe, we received more value than we ever could have expected—this was an incredible investment for us.”