The Heart bandits | chicago
Chicago Proposal Planner
Your proposal deserves more than a beautiful setup. Michele and Marvin personally plan every Chicago proposal, bringing 16+ years and more than 10,000 proposals of experience to one of the biggest moments of your life.
Client Testimonials
Your Chicago Proposal, Personally Planned
Planning a proposal in Chicago can mean finding the right location, navigating permits and weather, coordinating vendors, keeping everything a surprise, and making sure dozens of small details come together at exactly the right moment.
That’s where we come in.
Since 2010, Michele and Marvin have personally helped plan more than 10,000 proposals around the world. We bring that experience to every Chicago proposal we plan—from intimate moments overlooking the city to elaborate experiences created entirely around a couple’s story.
Why Couples Choose The Heart Bandits
16+ Years of Experience
We’ve seen what works, what doesn’t, and what can go wrong, and know how to plan for it.
Personally Planned by the Owners
You work directly with Michele and Marvin. We don’t hand your proposal off to an inexperienced planning team.
Creative Ideas That Feel Personal
We start with your relationship and the person you’re proposing to, not simply what’s trending.
Chicago Details Handled
Location, vendors, photography, décor, timing, logistics and backup plans are coordinated for you.
Real chicago proposals
Chicago Proposals We’ve Planned
Every custom proposal begins with your relationship, not a template. Here are a few of the stories we’ve turned into unforgettable proposal experiences.
Chicago Rooftop Proposal
For Diego, they love drawing photos of each other so we arranged to have a beautiful downtown rooftop rented just for them. The highlight was several art pieces depicting them as animated characters, ending in him on bended knee, which he then proceed to do in real life!
It’s a family affair
Their relationship was very family oriented. Because of this we arranged to have a beautiful setup on a rooftop with custom marquee letters. The biggest surprise came when all their families surprised them on this same rooftop immediately after.
Our Own movie night
For Jeff and Ali, their ideal date night had always been enjoying a cozy movie night at home or going to the movies. We arranged to rent out a private event space with flowers, candles, a popcorn machine, cozy seating, and a slideshow showing their favorite memories and ending in their proposal.
Ready to plan your Chicago proposal?
Tell us what you’re imagining. Michele and Marvin will take it from there.
How Chicago Proposal Planning works
Tell us your story
We learn about your relationship, your partner, your vision and what you want the proposal to feel like.
We Create the Plan
We help develop the concept, location and details that make the proposal feel personal.
We Handle the Details
We coordinate the Chicago location, vendors, décor, photography, timing and logistics.
You Show Up & Propose
You focus on your partner. We handle what’s happening behind the scenes.
chicago Expertise
Planning a Proposal in Chicago Takes Local Know-How
From the lakefront, wind and winter weather, to permits, crowd timing, and venue requirements, Chicago proposals come with their own unique considerations. We’ll help you choose the right location, navigate any restrictions, coordinate trusted local vendors and create a plan – including a backup if needed – so everything goes smoothly.
Still choosing the setting? Explore our favorite Chicago proposal ideas and locations.
Chicago Testimonials
What Our Clients Say
Michele and Marvin were absolutely wonderful in every possible way! They are organized, effective, fast to reply, and have amazing proposal ideas!
I recently proposed to my girlfriend (now fiancée) and chose to hire THB. I was new to the city of Chicago and had no idea what I could do or which places were even possible, therefore I thought it was best to ask for help.
Michele and Marvin were absolutely wonderful in every possible way! They are organized, effective, fast to reply, and have amazing proposal ideas!
My proposal was a huge success, their hard work definitely paid off and my girlfriend did not mind that I had professional help; on the contrary, she was absolutely delighted by how smooth everything went and how special the moment was.
I would definitely recommend THB for any proposal, they are experts in the field and will help you make this occasion as memorable, perfect and stress-free as possible!Michele ensured that everything ran smoothly behind the scenes, allowing me to focus entirely on the moment with my partner. We have been OVER the moon with joy!!
I cannot express enough gratitude for the incredible job The Heart Bandits did in coordinating my proposal.
From the initial consultation to the magical moment itself, every detail was meticulously planned and executed flawlessly! The proposal location was breathtaking, the timing was perfect and every element from decorations to the photographer, was expertly managed!
Michele ensured that everything ran smoothly behind the scenes, allowing me to focus entirely on the moment with my partner. We have been OVER the moon with joy!! If you’re considering hiring a proposal planner, this is your sign to go no where else! You will not get better communication and more caring individuals!
Frequently Asked Questions
Chicago Proposal Planner FAQ
Chicago adds its own layer of complexity like lake winds, winter weather windows, rooftop access, and a city that moves fast. Hiring a Chicago proposal planner means someone who already knows the terrain is handling the details, so you can focus on your partner instead of logistics.
We handle everything: location scouting, permits and venue coordination, vendor booking, timeline creation, weather contingencies, and keeping the whole thing a surprise until the moment you kneel. You show up and propose. We handle what’s happening behind the scenes.
Yes! From rooftop terraces overlooking the skyline to quiet spots along the lakefront or riverwalk, we know which locations actually offer privacy versus which ones look private in photos but draw crowds. We’ll scout and secure a setting that fits your story and keeps the moment just between you two.
Absolutely! Every proposal we plan starts with your relationship. Whether that means a custom art installation like we built for one Chicago couple’s rooftop proposal, or a private space designed around your own version of a perfect night in, we build the concept around you.
Yes. We work with trusted local photographers, florists, and musicians across Chicago and the greater Midwest, all experienced in proposal timing and discretion. We manage the coordination and communication so nothing gets left to chance or gets in the way of the surprise.
Chicago weather can turn quickly, especially near the lake, so every outdoor proposal we plan comes with a backup plan built in from the start. If wind, rain, or an early winter chill threatens the original setting, we already have an alternative ready to go—no scrambling, no delays.
Yes. Many rooftop, park, and public locations in Chicago require permits, insurance, or advance approval, and requirements vary by neighborhood and venue. We handle that paperwork and those relationships ahead of time so your location is locked in and compliant before the day arrives.
We recommend reaching out at least 4–6 weeks ahead, especially if you have a specific rooftop, season, or venue in mind—popular Chicago locations and vendors book up fast. That said, we’ve also pulled off proposals on much tighter timelines, so it’s always worth asking.
Ready to Create a Chicago Proposal They’ll Never Forget?
Tell us your story. Michele and Marvin will take it from there.