5 Chicago Proposal Planners to Help Pop The Question

Wedding planning is a journey all its own, but the process of getting engaged is just as exciting—so why not put just as much planning into it? Whether you have something intimate or over-the-top in mind, a Chicago proposal planner helps bring your vision to life (and keep it a secret!). "A proposal planner is someone who is dedicated to curating an unforgettably unique experience for the client," says Michelle Medina, the founder, owner and planner behind NORA Events. Proposal planners in Chicago typically work with the proposer a few months in advance to secure a location, lock in a photographer, florist, musician or any other vendors involved, and concoct a plan for getting the proposee on-site without a clue of what is happening. (Lately, there has been a trend of having a surprise engagement party right after the proposal—or at least having friends and family waiting in the wings to pop champagne; proposal planners can help orchestrate those events, as well.) And, just like each wedding, each proposal is unique. From epic rooftop proposals to intimate at-home ones, each tells the story of the couple. "One trend we are seeing is recreating a very important place in your love story, be it your first vacation location or first date setting," Medina says. "This has been really fun [to see] and allows us to personalize the setting." Keep scrolling to learn more about Medina and four other top wedding proposal planners in Chicago. Explore The Knot Vendor Marketplace to find even more (pro tip: search under wedding planners, then filter expertise by "getting engaged").

Christine Janda Design & Events

Photo: Christine Janda Design & Events

Christine Janda does it all when it comes to weddings: She's a planner, designer and floral artist, and she recently opened a wedding venue, Bloom Events. (Plus, her track record is backed by high-profile clients like Bachelor in Paradise alums Serena Pitt and Joe Amabile.) But her expertise begins even before the wedding: She plans Chicago wedding proposals, too. "The proposer who comes to Christine Janda Design & Events wants to create a truly personalized, memorable experience for their fiancé," Janda says. "They aren't simply looking for a trail of rose petals—they want it to look, feel, sound and be something that is their very own." Janda and her team work with the proposer—typically starting three months or more in advance—to create the perfect plan, "often one with a sense of mystery and whimsy, as there is nothing more special than a surprise proposal," she says. Pricing is dependent on the vendors involved and the elaborateness of the plan. She recently orchestrated a romantic at-home proposal for a client. "We created the most gorgeous intimate setting that bounced from room to room, crescendoing to the big reveal from soft muted whites and blush to a full spectrum of jewel-toned flowers, with a personal chef dinner finale." Intimate proposals are trending—sort of—she says. "I love when the big question is an intimate moment just for the two of you, then is followed by a surprise element with family and friends."

Visions Event Studio

Photo: Visions Event Studio

Owner and lead planner Jenée Strickland had a vision—pun intended—when she launched Visions Event Studio in 2010: to be the first planning firm in Chicago exclusively dedicated to proposals. The singular focus sets her apart and has led her to plan some incredible "will you marry me" moments. A favorite was last year: "Months of preparation went into what [my client, Nishanth] envisioned as a 'progressive proposal'—a full-day experience rather than a single moment on bended knee," Strickland says. "He designed a personalized scavenger hunt curated to include significant places from their relationship. The final destination was Trump Tower, where a team was ready to pamper her with hair, makeup and a new outfit. Aimen was visibly overwhelmed when the moment finally came where he knelt to propose. After a few intimate photos, the couple and their friends continued the celebration aboard a chartered boat." Stickland's proposal packages, which start around $1,000, involve a strategy session, full event conceptualization (and cover-up!), vendor and contract management and execution. "At Visions Event Studio, every client benefits from our one-planner guarantee, ensuring that each detail—from the initial brainstorming session to the moment on bended knee—is managed by a single dedicated planner," she says. Book the Chicago proposal planner at least two months in advance.

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NORA Events

NORA Events owner and planner Michelle Medina is known for coordinating some of the most epic weddings in Chicago and its surrounding suburbs—she recently orchestrated the nuptials of The Smashing Pumpkins frontman Billy Corgan and fashion designer Chloe Mendel at their home in Highland Park—but also takes pride in planning epic proposals. (A recent favorite? This rose-studded holiday proposal in the Cupola at LondonHouse, after which the couple's family jumped out from the outdoor snow globes to surprise them.) Her Chicago proposal packages range from $3,000 to $5,000 depending on the elements involved, and Medina and her team help with everything from venue selection to vendor coordination, including live musicians, private chefs, photographers, videographers and more. "Our service allows our clients to focus entirely on the moment and brings them the confidence to know every element is perfectly orchestrated for an unforgettable experience." The earlier you book, the better, but Medina has turned around proposals in as little as three weeks. "What makes each experience special and different is the love story," Medina says. "We love a good love story—and love even more to incorporate details in the proposal that tell that story."

The Heart Bandits

After Marvin Velazquez proposed to his girlfriend Michele in 2010, he admitted how difficult planning the perfect moment had been with no help. It sparked an idea, and the couple—who now have two children and reside in California—launched The Heart Bandits to help others just like him propose in extra-special ways. They have teams of day-of coordinators across the country to bring custom proposals to life just about anywhere, including Chicago; Chicago proposal packages cost $1,599 plus proposal expenses, and they recommend planning one to two months in advance. "The biggest proposal trends right now are heart arches and cold sparklers—we get this request multiple times a day," Michele says. "My favorite Chicago proposal was when we rented out a rooftop and had the [bride-to-be's] whole family waiting for her near the door. As she walked out toward a red carpet lined with candles, each family member handed her a red rose. Then she walked over to where her partner was waiting and he dropped to his knee to propose in front of large 'Marry Me' letters."

Amber Walker Events

Photo: Amber Walker Events

Proposal planner Amber Walker has been featured in The New York Times and countless other publications—and for good reason: Her proposals are some of the most over-the-top experiences. There's a price tag to match, with packages starting between $5,000 and $10,000 and going all the way up to $20,000+. "The sky's the limit when it comes to creating your perfect moment," Walker says, who is based in Toronto and Los Angeles but plans proposals all over the world. "During your consultation, we'll explore various budget ranges. Whether you envision lush floral arrangements, iconic landmark venues or over-the-top details that go beyond the setup, we're here to bring your dream proposal to life." Walker plans every proposal herself alongside a dedicated team—clients speak directly to her during the consultation and beyond—and leans on a Chicago-based event manager to bring the Windy City moments to life. She recently orchestrated a romantic Chicago marriage proposal on a terrace at the Ambassador Hotel, overlooking the skyline. "We designed a beautiful floral arch with her favorite flowers and colors, adding a personal touch that made the moment incredibly special," Walker says. "Private settings like home proposals or secluded beaches are popular, while experiential proposals—such as cooking classes, private boat trips or custom scavenger hunts—are also on the rise." Book at least one to two months in advance, as Walker's calendar fills up far in advance. "We're passionate about love and are dedicated to helping as many people as we can create their perfect, magical day."