If you know anything about me you know that I adore the city of Chicago! The beauty of the city, the people, the food, the scope of it all, there is just SO much that makes Chicago the truly incredible city that it is. That’s why it’s so easy to see why so many people decide to propose/kickstart the rest of their lives here in the city. There are so many incredible locations for a proposal throughout Chicago, it can honestly be a little overwhelming when you actually start to plan out your proposal! That’s why I put this article together to break down your proposal planning process as well as give you my seven favorite spots in the Windy City for a proposal. Let’s get into it!
Before we can take a look at my favorite places in Chicago for a proposal we first need to go over a couple of things to figure out exactly what you’re looking for in a proposal space. There’s often a lot of pressure when you start planning your proposal, so it’s easy to overthink things or forget certain things to consider with everything going on.
One of the first things you should consider is the time of year you plan on proposing. With Chicago being in the Midwest we deal with A LOT of weather changes, so it’s important that you prepare and plan your proposal for the weather you hope to have. Fall and Spring tend to have a bit more unpredictability to them but also have the less extreme temperatures, where Summer and Winter are the opposite, having their extreme temps but staying consistent for the most part. After your proposal you’ll be walking around your Chicago location for a little while for some more photos with your photographer, so decide on a season that you’ll be comfortable with doing this in. And lastly, as the date approaches keep an eye out on the weather in case you need to adjust our plan!
Do you want your proposal to just be an intimate moment between the two of you? Do you plan to have family and other guests present? Are you comfortable with strangers being around while you propose? These are all questions to consider when planning your proposal location as Chicago has a LOT of people living here. If you are wanting to have your proposal at a more popular location you can opt for a sunrise session to avoid some of the crowds.
Your proposal is one of the most important steps of your relationship as it’s what really kicks off this next chapter of your lives together. This is an incredibly special moment for the two of you so if you’re able to incorporate things from your relationship that means a lot to the both of you that is a huge plus. For instance, if one of your first dates was touring the Field Museum a proposal at Museum Campus would be a nice touch. Locations that mean something to both of you just make your proposal that much more emotional and special to your relationship.
Lastly, don’t be afraid to talk with your photographer to get their input and recommendation as you plan to make sure that your plans line up with your vision. We as photographers have had a lot of experience photographing different proposals. We know what works and what doesn’t, what’s realistic and what is not. Your photographer is your greatest resource when planning your proposal, so use them to help make sure you have the best proposal possible!
First up we have Milton Lee Olive Park which is on this list for a number of reasons. The park has an incredible view of the skyline, and even so, is not super busy at any time of day. That combined with the large amount of parking nearby and the park’s easy access make this one of the easiest and most enjoyable proposal locations in Chicago. Being out in the park and on the water of Lake Michigan, we are at full mercy to the elements though so be prepared for any changes in the weather.
One of, if not THE most iconic locations for a proposal in Chicago is North Avenue Beach, and for good reason. The skyline view from the beach is second to none, and being able to get right next to the waters of Lake Michigan and walk along them for some photos after the proposal is a huge plus as well. North Ave Beach is one of the more popular locations in the city so opting for a sunrise proposal to avoid the crowds is a good idea. The added beauty of the sunrise is a nice touch too!
The Honeycomb in Lincoln Park is one of my favorite locations for a proposal in Chicago as it has a ton of beauty in different forms. The Honeycomb itself is beautiful and offers an incredible view of the Chicago skyline. Being located in Lincoln Park is a huge plus too as you can walk throughout the park for the rest of the session and get some photos with the park’s beautiful greenery in addition to the city skyline. The park is a little on the busier side, but luckily there is enough space that people are typically spread out enough to give you some privacy for your photos.
Next up is Chicago’s Museum Campus which has some of the best views the city has to offer, both of the skyline and Lake Michigan. This beauty and the attractions of the campus itself bring in a ton of people though, so be prepared for some crowds. It’s also a good idea to look at what events are happening in Chicago the day of your proposal as if there’s a Bears game or an event at one of the other locations on Museum Campus parking will become an issue and there will be even larger crowds.
Located along the Chicago River, Ping Tom Memorial Park offers some incredible city views without being on the lake. The park is one of Chicago’s better-kept secrets as it has some truly breathtaking views but is much less crowded than some of the other locations on this list. The park also has a nice covered area, so even if the weather changes all of a sudden the day of, we can still make your proposal happen!
One of my favorite options for a proposal in Chicago is at your favorite restaurant! This is such a personal thing to your relationship and can really make the proposal that much more special. There will likely be other people there at the restaurant which you should be prepared for, but on the plus side of that, it makes it VERY easy to disguise your photographer. There are so many incredible restaurants in Chicago so the possibilities are really endless here. Just be sure to call ahead and let the restaurant know so they’re prepared!
Lastly, keep things personal and have your proposal in your favorite neighborhood in Chicago. Whether it’s the one you live in, the one you love to visit, or somewhere new you two have always wanted to explore. There is so much charm and beauty throughout the streets of Chicago perfect for a proposal. Side streets are a little less busy, but this is another case where having your photographer nearby and disguised is incredibly easy.
As I mentioned before there are just SO many places in Chicago that are perfect for your proposal, it’s all about finding the one that’s right for you. If one of these spots sounds right for you, or if you have another idea for your proposal and you still need a photographer I’d love to be a part of it! Head to my contact page here and we can start planning!
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