So, you’re planning on proposing to your best friend. First off, congratulations! This is such an important moment in your life, and you need a way to make it memorable. That’s why I’m here! I am a Chicago wedding photographer, and I have a passion for telling every part of your love story, including your engagement. Over the past years, I have been lucky enough to support countless couples throughout their proposals. From the places to the details, I would love to give you some tips on how you can consider proposing in Chicago.
As a photographer, lighting is always one of the top things on my mind throughout sessions. If you want professional photos of you proposing in Chicago, it needs to be something you’re considering as well! I would highly suggest choosing a spot with tons of natural lighting. Sunrise or sunset tends to be ideal because the light is diffused perfectly, letting you avoid all the harsh light of midday. And because this is the Windy City, consider the temps so you’re not sliding a ring onto a frostbit finger!
Some people prefer big, flashy proposals that let them announce their engagement to the world. Others, not so much. If you are wondering what would be better for you, consider your partner. If they have a flair for the dramatic, go crazy! Just be sure you know ahead of time the answer is yes. Personally, I tend to prefer private proposals so that your pics aren’t flooded with curious onlookers excited to share the moment. Really, it comes down to what makes the most sense to you both.
You’ve probably thought about this moment a lot, but trust me, you simply cannot overthink it! Before it’s time, go through all the proposing details for your Chicago engagement. Are you dropping down on one knee? Are you saying their name? What are you going to say? Will a folk band magically appear from the heavens and sing a love song? Make your plan and be sure to detail it to your photographer so they know what to look for.
The next thing you need to consider is where you will propose. Luckily, we have some pretty amazing spots around here. If you are looking for Chicago spots at the moment, here are some of my faves.
1601 N. Jean-Baptiste Pointe DuSable Lake Shore Drive, Chicago, Illinois 60610
North Avenue Beach feels like a celebration of Chicago when proposing. With this area, you can propose the entire city skyline as your backdrop. It feels particularly magical as the sun starts to set beneath Lake Michigan. Once you’re done, you can walk around the beach and get some pictures in the sand.
85 East Wacker Drive, North Michigan Avenue, Chicago, Illinois 60601
LondonHouse (located inside the London Guarantee Building) puts you up amidst the clouds for your proposal. As you pop the question, you will have 360-degree views of the city. They do require a reservation for your engagement, but they will hook you up with rose petals, a private rooftop cupola, and a bottle of Dom Perignon.
233 S Wacker Drive, Chicago, Illinois 60606
With Skydeck Chicago, you’ll float over the city when proposing. The Ledge tends to be the most popular spot for proposals, giving you a glass box overlooking the skyline. Just note this is a popular spot for tourists, so you may need to try to find hours when it’s less congested. I recommend early mornings on a weekday.
875 N Michigan Avenue, 94th Floor, Chicago, Illinois 60611
360 Chicago offers a similar experience to Skydeck with tilting glass boxes peering down over the city. They offer a proposal package that includes special lighting, rose petals, drinks, and a semi-private box that you can use for up to an hour.
South Bank of Chicago
I always love the Chicago Riverwalk because it puts you in the heart of the city while offering countless backdrops for proposing. As you make your way along the 1.25 miles, you will pass by several districts, including The Civic, The Arcade, The Confluence, and The Esplanade. You will have plenty of options for your surprise proposal!
300 N. Central Park Ave, Chicago, Illinois 60624
With Garfield Park Conservatory, you can have lush greenery even in the coldest Chicago winters. The botanical garden contains thousands of plants from across the globe. And because it’s indoors, you’ll never have to worry about rain showing up on the forecast.
E Ohio Street, Chicago, Illinois 60611
Milton Lee Olive Park is a scenic space that puts a little bit of nature into the center of the city. The walking paths are perfect for taking a stroll with the skyline just beyond you. There is also a landing where you can propose while overlooking Lake Michigan. This is yet another spot that comes alive during the sunset!
201 E. Randolph Street, Chicago, Illinois 60601
If you are looking for legendary Chicago landmarks, you might want to consider Millennium Park for proposing. Not only does it have The Bean, but you can also find other artistic sculptures as well as some of the best architecture in the city!
209 South LaSalle Street, Chicago, Illinois 60604
The Rookery Building is a historic space that is as elegant as it is impressive. Inside, you’ll find lavish details, including gilded facades and winding staircases. Outside, you will have private balconies with limestone railings. No matter the spot you choose, you’re going to have a dreamy backdrop!
1 E Erie St Ste 525, Unit #2000, Chicago, Illinois 60611
If you really want to turn your proposal into an adventure, Heli Chicago might just be for you! With this option, you can board a helicopter and fly over the city before it’s time to ask the question. It’s private, and it’s completely unforgettable!
So, how necessary is it to hire a photographer? I think it’s extremely important, and I promise this is not coming from a bias. Your nerves are going to be through the roof, and there’s a good chance you’ll forget all the details one day. With pictures, you will be able to capture every single second! Trust me, your partner is going to be grateful you did. Now, you just need to find the right one.
The first step is to search through potential photographers and find the one that matches your style. Be picky! Pay attention to everything from their response promptness to their eye for detail. Once you have your person, you need to iron out all the fine print. How are they going to support you? Personally, I love working with my clients on all those details, including locations. I’ll be in constant communication via phone or email so you know what to expect. We will work out where you can find the best lighting to stand, where I should be positioned, how I can hide ahead of time, and what your proposal will look like.
Following the actual proposal, we’ll take several engagement pics in the area that celebrate for you. That same day, you will have 10 pictures you can share with your friends and through social media. Then, within a week, you’ll have a full gallery. These will be great for everything from engagement announcements to framed prints!
Hopefully, this guide helps you with proposing in Chicago. If you could still use some help, though, just let me know. I would love to tell you all about my proposal options so you can decide if I’m the one to help you celebrate. Send me a message to find out more!