A surprise proposal can be one of the most fun and exciting parts of a relationship, especially when you’re planning it in the greatest city around, Chicago! That being said though there’s often a good bit of pressure that comes along with planning your proposal. The last thing you want is to be stressed out and overthinking your proposal, which is why I put this guide together to walk you through everything you need to know when it comes to planning the perfect surprise proposal in the Windy City!

Go Back to the Basics

When it comes to starting the process of planning your proposal in Chicago, you’ll want to start with the basics and start planning a couple months in advance.  You want your proposal to be thoughtful and caring, and as you’re planning you’ll want to keep what your partner wants at the forefront of your mind!  Start by reflecting on you and your relationship and the reasons you love one another.  Pull from these thoughts as you begin the planning process and remember that your proposal can be as simple or as elaborate as you would like it to be!

BOOK YOUR PHOTOGRAPHER

If you decide you want this moment documented, you’re going to want to make sure that you plan ahead!  You will want to book your photographer a couple of months out if possible.  Weekend dates, especially in the busy months of the year, are extremely hard to find when it comes to booking a photographer and can be almost impossible if you’re planning your Chicago proposal last minute.  If you do happen to be planning your proposal less than two months out, having flexibility in the date you plan to propose in Chicago is key to finding a local photographer. 

Once you have your photographer, you can finalize your date and time, and if you don’t already have a location picked out, your photographer can be a great resource for choosing a location that will best fit your vision.  When you contact your photographer, it’s helpful to present a couple of ideas to them so that they can help guide you through figuring out the next steps and putting the finishing touches on your plan. We as photographers have been around PLENTY of proposals, so we’ll know what works and what will need adjusting!

The Who What When Where How

As you begin daydreaming about what you would like your proposal to look like with your partner, you will want to start with the questions who, what, when, where and how.

When to Plan Your Proposal in Chicago

Once you begin the planning process for your Chicago proposal, you will want to start with choosing a date.  There will more than likely be a handful of factors that play into choosing when to have your proposal such as when you will have your ring, when family and friends can get into town if you want them to be there, and your general relationship timeline.

As you choose when to have your proposal ask yourself the following questions to help narrow down a time to propose.  When do you hope to be married?  How much time do you hope to have for planning your wedding day?  When will you have your engagement ring by?  And last but not least, what season/weather do you envision having when you propose.  Once you decide on a when, you will want to contact your photographer.  

Where to Have Your Chicago Proposal

As you get further along in the planning process you will want to start thinking about where you want to propose to your partner.  You’ll want to choose a location that you can get your partner to without raising any flags.  You will also want to think through your vision for your proposal and how intimate you hope it will be.  If you want a lot of hype and want to be immersed in the people of Chicago, choosing a location like the River Walk, the Wrigley Building, or North Avenue Beach for your proposal are all incredible options!  If you would rather have a more intimate experience, you might opt for sunrise at North Avenue beach, Milton Lee Olive Park, or your favorite spot in your neighborhood for a little more privacy while you pop the question.  

Some of my favorite proposal spots in Chicago:  Milton Lee Olive Park, North Avenue Beach, the Lincoln Park Honey Comb

For more location ideas and more information on my top locations for proposals in Chicago, check out this blog post which covers 7 of my favorites in the Windy City!

Who Would You Like There With You if Anyone?

If you haven’t had a conversation with your partner about who they hope to have there during or after their proposal, start to think through some of the most important people in their life outside of you.  Once you have a general list, decide how you hope to celebrate your proposal with these loved ones.  Do you want them to be there with you two?  Do you want to meet up with them later that day?  Or, would you rather have the day to yourselves and celebrate on a later date?  There are no right or wrong answers here!

If you do have a handful of people you end up wanting present for your Chicago proposal, you will want to contact them as soon as you finalize your date.  Give these people a call, let them in on the plan and let them know how they can be a part of it!

What Will You Use to Get Your Partner to the Proposal

When you bring a photographer into the proposal plans, your plan will have to be a little more structured than if you were to fly solo.  You will have to put together a plan to get your partner to the proposal location during the time you have your Chicago wedding photographer booked.  This is where the “what” comes in.  What will you tell your partner you are doing together to get them to the designated location for their proposal? 

Most of my couples will plan their proposal during a city excursion, at a location on the way to something else, or make up another event that is happening at the proposal location.  Engagement parties for other friends, meeting a work client at your favorite Chicago restaurant, or just checking out a cool location you love or haven’t been to before are all great ways to get your partner to the designated spot!

How Would You Like to Propose?

Last but not least, you will want to think through how you want to pop the question!  Is your partner obsessed with grand gestures?  Do they prefer to keep things simple and straight forward?  Are they family people that would love to have everyone present for the moment?  There are so many unique and creative ideas for proposing to your partner! Think about your relationship so far and try to mold your proposal based on the things you know your partner loves and how their brain works.

How it Works

Inquire with Your Favorite Chicago Photographers

It’s important to inquire with your wedding photographer early in the planning process so you can lock down a date and have someone to reference and bounce ideas off of as you plan.  If you’re ready to start planning your proposal, head to my contact page and we can start planning your dream proposal together!

We Start Planning Your Chicago Proposal

If you don’t have a location in mind we can work together to brainstorm ideas.  We will make a plan and you will put together a ploy to get your partner to that location i.e. you’re meeting your family there for lunch, etc.

Saving My Number Under a Friend of Family Members Name

After we book, I recommend saving my email under a new name in your contacts for one of your favorite stores so they appear in your email as a promotion.  Then as for your contacts, if we are texting as we plan your proposal, I recommend you save my name as someone in your family that you text fairly regularly! This keeps your honey completely unsuspicious in the event they happen to see a notification pop up on your phone.

Sharing Your Location

The day before I will ask you to share your location with me so I can monitor your location the day of, especially if we haven’t met before.  This will help us to make sure we are both in the correct spot, and if there are a lot of people around, having your location will help me to make sure I’m ready to document the moment if I don’t see you right away.

The Best Times of Day For Your Chicago Proposal

Sunrise Proposal in Chicago

Sunrise is a great time for proposal for a number of reasons, one of the biggest of them being, the lighting is really soft, even, and great for photography.  If you plan a sunrise proposal in Chicago, you can plan to really have any public park to yourself outside of a handful of runners.  Though it may be a bit more challenging to get your partner up for their proposal if you aren’t naturally early risers, it’s definitely worth it.  Not only will you have a breathtaking view, but the peaceful nature that comes with Chicago at sunrise is also beyond worth it.

Sunset Proposal in Chicago

Much like sunrise proposals in Chicago, sunset proposals also have some really epic lighting that is paired with them.  The lighting is soft and glowy and even, and if you’re by the lakefront, the sun will be changing colors and peaking through the buildings that make up Chicago.  Sunset proposals are breathtaking though they do tend to be a bit more crowded if you’re using a public space for your Chicago proposal.  

Midday Proposal in Chicago

When planning your proposal, if you plan to have your proposal midday, your photos will look a little bit different than they will later in the day.  Your backgrounds will be brighter, your faces might have a bit more shadow on them if you propose in full sun, and it might be harder to see the backdrops of your images.  I do frequently suggest avoiding a midday proposal if outdoors, but if you are planning to propose indoors, midday is a great time to pop the question because of the abundance of light.

Now that you know the ins and outs of planning your surprise proposal in Chicago, it’s time to start the planning process! If you need some inspiration for your Chicago Proposal, check out this one at Milton Lee Olive Park I photographed. And if you’re ready to book a photographer for your proposal head over to my contact page here!