Best Places to Propose in Chicago

For this blog, only outdoor locations will be featured. Indoor locations are a blog of their own.

Choosing an outdoor location for one of the most important moments in your life can be intimidating. Pair that stress with combing through various locations in one of the biggest cities in the world can really seem overwhelming. The good news is that I am here to help! I photographed my first surprise proposal in 2016 on Kinzie Street Bridge. The concept of hiring a professional to capture a surprise proposal was a brand new trend and few people were booking that service. Fast forward to now and it’s almost a must-have for most couples. As a Chicago wedding photographer of over 15 years I know all the best locations and the pros and cons of each. In this blog I will name some of the best places in Chicago to propose and give tips on the best way to choose a location for your Chicago surprise proposal.

To get a full “How To” plan a surprise proposal, check out my separate blog here.

Let’s dive in! Here you will find all my favorite places to propose and the reasons why each location is fantastic. First let’s chat about what questions to ask yourself when considering a location other than is it a beautiful iconic place because let’s be honest all these places are aesthetically pleasing, that’s why they are so popular.

What is my ( or my fiance’s ) preferred aesthetic? In Chicago you have 3 outdoor aesthetics to choose from. Those 3 categories are Skyline, Nature/Lake View or Urban/Downtown ( non-tourist vibe ). Once you narrow this down you can ask yourself the next question.
How private do I want the location to be? If you are a private couple that doesn’t want tourists to be gawking or taking their own phone photos, you will want to choose a place that’s more secluded and off the beaten path. You don’t have to sacrifice an iconic backdrop like a skyline in order to get privacy. When you hire me, as part of your consultation, I will give suggestions of a location that has both a favorable backdrop as well as privacy.
Will my fiance want a location that means something special to them? Does the location I have chosen have sentimental value to us as a couple? If you want to account your partners opinion in the location you choose, it’s a good idea to consider what location will really give them the wow factor.
What will the storyline be ? How do I get my partner to this location for the proposal? You want to choose a location that will not be out of the ordinary for you as a couple. It goes without saying that when pulling off a surprise proposal, you want your partner to be SURPRISED ! Many couple’s that come to me, are from out of town and they are just visiting Chicago on vacation. In this instance it’s an easy cover story to just be visiting great tourist spots because the excuse to be there is just to see iconic sights. If you are a native Chicagoan, it’s trickier to come up with a story, so best of luck !
Is it important to me for my partner to look their best in the photos? If the answer to this question is yes, then your next question will be, ” What do I tell them to get them to be dressed up? One way to get your partner to “dress up” is to create a plan that ends with you going somewhere upscale like a dinner or a night on the town. This way they won’t suspect anything is going on. This is another thing to keep in mind when choosing a location because you will want to choose a location that isn’t too far from the final destination in the story line.

Once you have the answers to all these questions, you will be set to choose where the engagement will take place. Check out these photos from the most popular places in the city. Now you are ready to book me as your photographer !

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Gibson’s Italia at River Point Park