Planning a Chicago Proposal From Out of State
You handle the flight and the ring.
I handle everything in Chicago.
Most of the proposals I photograph are planned by someone who does not live in Chicago. You are flying in, you have one shot at the moment, and you are coordinating it from hundreds of miles away. That is exactly the situation I am built for. I know the locations, the light, the permits, and the timing, so you can land and focus on her.
Collections From $795
Same pricing as local clients. I live here, so there is no travel surcharge.
Tell me your date and your city. I will send back a plan: the right location for your timeline, sunset timing, a weather backup, and exactly how the day will flow. You will know everything before you book your flight.
300+ Proposals Captured · 151+ Five-Star Reviews
You do not need to know Chicago. I do.
Some of my favorite proposals have been planned entirely by text and email with someone who had never set foot in the city.
Maybe you met in college here and moved away. Maybe she has always wanted to see Chicago and you are turning the trip into the moment. Maybe you live in Houston, New York, Los Angeles, or San Francisco and you are flying in for a long weekend with a ring in your bag.
Whatever brought you here, the hard part of an out-of-town proposal is not the question. It is everything around it: picking a location you have never stood in, timing it to the light, coordinating it around a dinner reservation, and having a backup if Chicago weather does what Chicago weather does. That is the part I take off your plate completely.
What I handle so you do not have to
When you are planning from another state, you are working blind on the details that matter most. Here is what I take care of before you even land:
- Choosing the right location for your date, your timeline, and the light, based on 300+ proposals across this city.
- Sunset and golden-hour timing, coordinated around your dinner reservation or other plans.
- A weather backup for every location, decided early so you are never scrambling the morning of.
- Scouting the exact spot, the hiding position, and the angle in advance. You never have to describe a place you have never seen.
- Coordinating the signal and timing by text so the surprise stays a surprise, even with the time difference.
- Working with your hotel or restaurant when the moment involves one, so the logistics are handled on the ground.
How it works from another state
You send me your date and your city
Tell me when you are coming, where you are flying from, and any rough idea you already have. If you have no idea where to propose, that is completely fine. That is what I am for.
I send back a real plan
The right location for your timeline, the best time of day for the light, a weather backup, and how the moment will flow. You will know exactly what the day looks like before you book anything.
We lock the details by text or a quick call
No need to be in Chicago to plan it. We handle everything remotely. By the time you land, the only thing left to do is the part only you can do.
You arrive, I am already in position
On the day, you give me a simple heads-up by text when you are close. I am hidden and ready. You walk her in, I capture the moment, and then we celebrate with portraits.
You get the photos before you fly home
Highlights land within 48 to 72 hours, so you can share with family while the trip is still happening. The full hand-edited gallery follows within about a week.
Collections
Same pricing as my local clients. I live in Chicago, so there is no travel surcharge on my end.
Collection 1
$795
- Discreet proposal coverage
- Portraits right after the yes
- Full remote planning included
Collection 2
$895
- Discreet proposal coverage
- Extended portrait session
- Ideal for most out-of-town visits
Collection 3
$985
- Discreet proposal coverage
- Expanded portrait session
- Required for multi-location plans
The Cinematic
$1,795
- Two simultaneous angles during the proposal
- A senior second photographer alongside Jeremy
- Multi-location flexibility
- Best for a destination weekend you want fully documented
For out-of-town couples turning the proposal into a Chicago weekend, Collection 2 or 3 tends to fit best. The extra portrait time means you fly home with a real gallery of the city, not just the moment itself.
Frequently Asked Questions
The questions I hear most from couples planning a Chicago proposal from out of state.
I have never been to Chicago. Can you still help me pick a spot?
Yes. This is the most common situation I work in. Tell me the vibe you want and your timeline, and I will recommend the location based on 300+ proposals across the city. You never have to know Chicago to propose here well.
Do you charge extra because I am coming from out of state?
No. I live in Chicago, so there is no travel cost on my end. You pay the same Collection pricing as any local client.
How do we plan everything if I cannot meet in person?
Entirely by email, text, and a quick call if you want one. I send you a full plan: location, timing, weather backup, and how the day will flow. We lock the details remotely. You handle nothing on the ground until you arrive.
What happens if the weather is bad the day I fly in?
Every location I plan comes with a backup. I watch the forecast as your date approaches and help you make the call early, so you are never deciding in a panic the morning of.
How will the timing work with my flight and the time difference?
We build the plan around your travel and any dinner or hotel reservations. On the day, you simply text me when you are close to the location and I am already hidden and ready. The time difference never becomes a problem.
When will I get the photos? I want to share with family on the trip.
Highlights within 48 to 72 hours so you can share while the trip is still happening. The full hand-edited gallery follows within about a week, after you have flown home.
Can you help coordinate with my hotel or the restaurant?
Yes. When the moment involves a hotel rooftop, a restaurant, or another venue, I help coordinate the on-the-ground logistics that are hard to manage from another state.
What if we want to turn it into a longer Chicago shoot?
Collection 3 or The Cinematic gives you time for a second location and a real portrait walk through the city. Many out-of-town couples use the proposal as the start of a weekend and want the gallery to reflect that.
How do I get the ring through TSA without ruining the surprise?
Keep the ring in your carry-on, never your checked bag. You do not need to take it out of the box at security. If you are worried about a hand search giving it away while your partner is next to you, ask the agent quietly for a private screening. They handle this constantly and will not make it a scene.
What if my flight to Chicago is delayed or canceled?
I build flexibility into every out-of-state timeline. If your flight slips, text me as soon as you know and I will adjust the proposal time or move us to an indoor backup location so the moment is protected. Travel is the one thing neither of us controls, so I plan for it from the start.
How do I find the exact spot if I have never been to Chicago?
On the morning of your proposal I send a live map drop-pin straight to your phone, along with a photo of exactly where I will be positioned. You just walk to the pin. You never have to navigate a city you do not know while also trying to stay calm before the biggest question of your life.
Tell me your date and your city.
Send me where you are flying from and when. I will send back a real plan you can build your trip around, before you book a thing. The hardest part of an out-of-town proposal is the part I take care of.
Start PlanningPrefer to reach out directly? Call or text (847) 212-8642 · jeremy@jeremyglicksteinphotography.com
Start planning your Chicago proposal
Tell me your date, the city you are flying from, and any idea you already have. I will reply within a couple hours during waking hours with first thoughts on location, timing, and how the day can flow.