Sometimes the best way to plan your own proposal is to picture a few that worked. Here are the kinds of moments we design across Chicago — use them as inspiration for yours.
The high-rise reveal
A couple thinks they’re heading up for sunset drinks. The door opens to a private room at a place like LondonHouse — skyline glowing through the windows, a heart of roses, and “Marry Me” in soft neon. They barely make it inside before the tears start.
The candlelit steakhouse
A quiet private dining room, transformed. Dinner reservation as the cover story, a heart arch waiting, and a celebration over their first meal as an engaged couple.
A North Avenue Beach sunset
For the couple who wanted outdoors, the one spot we recommend: the skyline across the water, golden light, a heart arch in the sand, and almost no one around. Here’s why we love it.
Ready to plan your Chicago proposal?
We design luxury heart-shaped floral arch setups with a glowing “Marry Me” sign, candles and rose petals — so all you have to do is get down on one knee. Packages from $500.
See Proposal Packages →The cozy at-home holiday
Snow outside, candles inside, the tree lit, family hidden in the next room. They step into the living room and everything has changed. The most personal kind of proposal there is.
The thread through all of them
Here’s something we tell every couple: in Chicago, the venue can make or break the moment. We lean toward indoor settings — steakhouses, a private room in a high-rise like LondonHouse, ballrooms and rooftop lounges — because they give us full control over privacy, lighting and that jaw-drop wow factor, with none of the parking, permit or crowd headaches. If you have your heart set on outdoors, our go-to is North Avenue Beach for the skyline view without the chaos. We gently steer couples away from packed spots like Navy Pier or the Adler, where crowds and parking can quietly sabotage the surprise.
Every one of these worked because the setting was controlled, private, and built around the couple. That’s the part we obsess over — so all you have to do is ask the question.
Want to see fresh setups as we create them? Follow along on Instagram and TikTok @omgeventschicago.
Ready to design yours? Let’s talk.
Let’s create your perfect moment
Tell us your date and your vision — we’ll handle every detail, from the venue to the last candle. Couples fly in from across the country to propose in Chicago with us.
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