Your proposal is one of the most exciting and important steps in the journey of your love story, which is why it comes as no surprise that it can also be one of the most stressful to plan. Thankfully, it doesn’t HAVE to be that way! Your proposal should be fun, a celebration of the steps you’ve taken to get here together, and a first step towards your life together as a married couple. I want you to be able to experience this moment and the joy that comes with it to the absolute fullest, which is why in today’s article we’ll be going over everything you need to know to plan your proposal in the city of Chicago!
Questions to Ask as You Plan Your Proposal in Chicago
Before we really dive into the nitty gritty details of planning your proposal, there are some questions you’re going to want to ask yourself first. The answers to these will help guide you through many of the decisions you’ll be making as you plan your proposal in Chicago.
Do You Want Your Proposal to be Photographed?
One of the earliest questions you’ll want to ask yourself is if you want your proposal photographed. This is a very personal question, and the answer really comes down to what you and your partner want. If your partner has voiced in the past how they don’t want the moment photographed you should respect their feelings.
If they’ve said they want it photographed, or you know that they’d like the moment documented even if they haven’t explicitly said it, there’s a bit more planning you’ll have to do. To start, I recommend reaching out to your photographer as early as you can. Between 2 and 3 months before your proposal is typically a pretty safe timeline to ensure you have a photographer that you like to document your proposal. The good news here is that once you have a photographer booked they can help with a LOT of the details and planning of your proposal. It’s hard to plan a proposal when it’s likely the first time you’ve ever been a part of one, whereas we photographers have plenty of firsthand experience to call back upon!
When Should You Propose in Chicago?
The next question to ask yourself as you begin the ideation process of your proposal in Chicago is when you want to pop the question. The great thing about Chicago is that every season has its own draw and appeal, and there are SO many locations that lend themselves beautifully to the seasons. For example, you may opt for a winter proposal in front of the tree in Millennium Park or the Wrigley Building if you’re fans of the holidays! If you’re more of a summer loving couple though you might instead propose during a sunset at North Avenue Beach before a date night out. Think through what you two both love about the different seasons of Chicago, and from there you can start to put the rough plan together for your proposal date.
Where Should You Propose?
As I mentioned above, Chicago has SO many beautiful spaces to choose from for a proposal. From natural oases in the Windy City, to historic and iconic buildings, and even the unique and charming neighborhoods that make up this wonderful city, the options are practically endless! Think about what you two love the most about Chicago and try to incorporate it into your proposal.
Do you love the hustle and bustle of the city and all of its people? A summer evening at North Avenue Beach or the Wrigley Building might be the perfect fit! Do you love the city’s skyline, but want something a little more private? Montrose Bird Sanctuary, Milton Lee Olive Park, or Alfred Caldwell Lily Pool are all fantastic options. Here’s a quick list of just a few of my favorite locations in the city:
- Your Neighborhood
- Your Favorite Bar or Restaurant
- Chicago Art Institute
- Milton Lee Olive Park
- Lincoln Park Nature Boardwalk
- Alfred Caldwell Lily Pool
- The Wrigley Building
- The Lincoln Park Zoo Lights (Holiday Season Only)
- Museum Campus
- North Avenue Beach
When choosing a location you’ll also want to pay attention to whether or not any permits are needed in order for photos to be taken, which is one of the many things I love to assist with when planning a proposal!
Planning the Details of Your Chicago Proposal
With a rough plan in place of what you want your proposal to look and feel like, it’s now time to start ironing out the details, starting with booking your photographer.
Find and Inquire with a Photographer
There’s a reason I recommend booking your photographer as one of the first steps of your planning process, and that’s because we can help with many of the other areas of planning! If you are proposing in the fall or early winter in Chicago you will want to reach out at least a few months in advance to your potential photographer. This is the busiest time of year for wedding photographers, and if you want a photographer with a specific style you’ll have to reach out early in order to ensure they’re available for your date.
I highly recommend having some flexibility when it comes to your planned proposal date when booking a photographer. If you plan on celebrating with your friends and family after the proposal, find a few dates that work for everyone and then bring those dates with you as you begin talking to wedding photographers. As you talk with your photographer with your potential dates in mind you should be able to land on a specific date that works for everyone. From there you can start planning some of the other details!
Run Through Your Plan with Your Photographer
As a photographer with 13 years of experience under my belt I have plenty of suggestions to offer when it comes to planning a proposal, but it’s also important for it to be unique to you. It’s your proposal after all, my purpose here is to document the moment and ensure that your proposal comes together exactly how you wanted! Once my client’s have booked me to document their proposal I’ll then ask them about what they want the moment to look and feel like. We’ll go over the rough plan, I’ll offer help with any questions they have, work through any concerning areas they might have overlooked, and from there come up with a concrete plan to make their proposal the best it can be.
Setting Up the Proposal
A crucial piece of planning your proposal in Chicago is getting yourself, your partner, and your photographer at the correct location at the same time. You’ll need to come up with a plan to do this while also minimizing any suspicions they may have, which is easier said than done as you’ll likely be pretty nervous beforehand! Use your chosen location to your advantage for this.
As an example: maybe you have dinner reservations in the city, but you “accidentally” scheduled them for 8 instead of 7, so you decide to walk around North Avenue Beach for a bit. At that point your photographer should already be there and ready to photograph the big moment when you pop the question!
Another fun way to do this, and a great option if you’re worried about ruining the surprise, is to plan a session around the proposal itself! Gift my photography services to your partner as an anniversary gift, and we can then include your proposal into the session with them being none the wiser. It’s the perfect ruse!
What Will You Do After the Proposal?
You’ve proposed, now it’s time to party! I always recommend my clients plan some sort of celebration for after they propose. It’s one of the most exciting moments of your journey through life thus far, and it deserves to be celebrated. Whether it’s a date night out for just the two of you, or a surprise engagement party where your closest friends and family are present, there are so many fun ways to enjoy yourselves after your proposal in Chicago!
A Few Helpful Tips
Presentation is Key
When it comes time to get your partner to your proposal location, you’ll want to think about how you would normally present plans to them. Are you the planner who usually organizes your date nights? Or are you more on the spontaneous side of things? If you’re the latter you’re going to have to push yourself a bit and come up with an inconspicuous plan that gets your partner to the proposal location! If you’re a planner though this is a much easier process as you can just set up the date on your calendar using the cover story you’ve decided on for your proposal date!
Prepping Your Partner
Think through whether or not your partner has set any expectations for you on what they hope their proposal is like. Do they want to have their nails done? If so you might want to book them an impromptu nail appointment a few times prior to the actual appointment for the proposal so they’re not suspicious with the one off session.
Do they want their family there? If that case you’ll want to make sure they’re ready to go! Prep them on the date and time, and let them know your rough plans. Check your partner’s phone for location sharing with any guests who will be in Chicago for the proposal, especially if they’re coming in from out of town, and turn this off for now. A single notification from location sharing can instantly throw a wrench into all the planning you’ve gone through!
Communicating With Your Photographer
Leading up to the proposal, if your cover story isn’t an anniversary session then there’s no reason you should be getting texts from a photographer right? This is why I recommend changing your photographer’s contact info in your phone to something inconspicuous. Use the name of a friend or cousin you talk to regularly, but not one that your partner would immediately want to answer for you if they had your phone. Sometimes I will even have my clients share their location with me so I can ensure I’m in the right place at the right time! I will also typically ask for them to text me and let me know what they’re wearing so I can keep an eye out for them at the location.
Try to Relax
Easier said than done, but try to enjoy the moment! Soak in this time you have together and really try to ground yourself as you get ready to pop the question. It’s SO easy to get swept up in the moment and block out everything that’s going on around you. Take some deep breaths, soak in how your partner looks, what they’re wearing, how you feel leading up to the moment, and think about the journey you’ve already been on together. Then last but not least, get excited! This is going to kickstart the rest of your life together as a married couple, how amazing is that?!
Ask for Help
Your people will be so excited to celebrate with you, and many of them will want to help in any way they can. Ask your loved ones to help with the planning and execution of your proposal. Whether they decorate your apartment for when you get home, take your partner out to get their nails done, or help you sell your cover story by talking with your partner about it, have your people help make your proposal easier for you, as long as you can trust them not to spill the beans early!
That just about covers everything you need to know in order to plan a proposal in the fantastic city of Chicago! Like I said earlier, there’s a ton that goes into making your ideal proposal a reality, but at the end of the day the work is so worth it, and with the right help and preparation you can make it significantly less stressful. If you’d like to have me photograph your proposal be sure to send me an inquiry through my contact page today!
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