I LOVE Chicago, especially for a proposal! The city is filled to the brim with so many cool and unique locations for you to pop the question to the love of your life. From gorgeous beaches and parks to jaw dropping city views and iconic locations, the windy city has it all. How do you decide which Chicago location is right for you to propose though you may ask. I wrote this article to answer that question and give you some ideas of incredible proposal spots in the city. 

How to Choose Where to Propose in Chicago

When deciding on exactly where you want to propose in Chicago there are a few different things that you’re going to want to keep in mind. First you’ll want to make sure that your location has more than just one spot for you to take photos at. Your photographer will hang out and work with you guys for a little while after you initially pop the question. Walking around and taking photos of the two of you with the surrounding scenery. 

Next you’ll want to figure out how busy your location typically is and if certain times are less busy than others. If you don’t want a lot of people around you during your proposal, then North Avenue Beach midday in the summer is going to be a no go. Early morning around sunrise is a safe bet for a lot of places to be less populated. Lastly as a bonus choose a spot that has some meaning to you. Whether that’s somewhere you both have a connection to already, or the space involves something you love like exploring the city together or being down by the lakefront. 

When to Propose in Chicago

If you’re wanting something a little more intimate, I highly recommend planning your Chicago proposal for a week day or earlier in the morning.  There are going to be less people out and around, and the probability of being able to book a photographer for your proposal will be much higher. This can vary by location as some are more popular than others, but as a general rule of thumb the earlier in the morning the better!

Top 10 Proposal Location in Chicago

Now that you know what to be on the lookout for let’s get into my list of the top 10 locations to propose in Chicago. This is by no means the end all be all list, as the city is huge and has so many great spots to pop the question. These spots are all incredible for proposing though, and even if they aren’t exactly what you envision they should help get your brain flowing for exactly what you are looking for in your proposal location!

North Avenue Beach

First off we have North Avenue Beach, the iconic beachfront on the north side of the city with an incredible view of the Chicago skyline. North Avenue Beach is a prime spot for a proposal in Chicago. Having a nice walk along the lakefront during sunrise while no one is around is the perfect way to start your day. Then once you’re in position you’ll have the amazing combination of the Chicago skyline and the water of Lake Michigan behind you as you propose. It makes for some truly epic photos and once we start the rest of your session post proposal there are so many spots at North Avenue Beach perfect for photos!

Ping Tom Memorial Park

Located on the southern side of the city in Chicago’s Chinatown, Ping Tom Memorial Park is a beautiful location for a proposal. The park is right on the Chicago River with a walkway right along the river giving you a perfect view of the city skyline. This is the perfect backdrop for any proposal. The park itself is also filled with some amazing paths, architecture and greenery giving you a lot to look at and work with for the rest of your session.

Adler Planetarium Skyline

I LOVE the walk along Lake Michigan at Adler Planetarium. This beautiful spot is part of Chicago’s Museum Campus and gives you one of, if not the best views of the city’s skyline making it a truly epic location for a proposal. There’s so much space along the lakefront walkway at the planetarium that even during busy times of the day there is still plenty of space for your proposal to happen without being surrounded by people. And with it being on Museum Campus the Shedd Aquarium, Field Museum and Northerly Island Park are all right next to you meaning you have plenty of options for your session.

Wrigley Field

This one’s for the couples that love baseball and the Chicago Cubs! Located in Wrigleyville the Cubs stadium is one of the most iconic parts of Chicago and makes for a great proposal location. Wrigleyville is one of the more poppin spots of the city so prepare for a few extra people around during your proposal, ESPECIALLY if it’s a game day. This can add to your overall experience though if hearing people cheer while you propose is your thing, and with there being so much to do in Wrigleyville we’ll have no shortage of places to head to post proposal.

Chicago Riverwalk

The Chicago Riverwalk is located in the heart of the city and is one of my favorite options for a proposal as there are SO many spots along the path that are perfect. The Riverwalk runs along the Chicago river and is a great option for couples that like to explore and adventure together. There’s so much to see along the Riverwalk, and being surrounded by the city’s skyscrapers gives your photos and the experience overall such an amazing sense of scale. It’s truly special, especially if you haven’t been on the Riverwalk or don’t frequent it often.

Garden of the Phoenix

The Garden of the Phoenix is a truly special place in Chicago. The garden is on the south end of the city next to the University of Chicago. It’s an island located in Jackson Park and it’s feeling of total removal from the city is legitimately magical. It’s amazing being inside the garden as you feel like you’ve left Chicago completely and entered into an oasis of lush greenery. The gardens themselves are absolutely beautiful and the removed feel from the city itself makes this an amazing spot for a more intimate proposal experience.

Milton Lee Olive Park

Located a short walk away from Navy Pier, Milton Lee Olive Park is a sweet little park that looks out over Lake Michigan.  Though this park is a little smaller than some of the others on this list it still is an incredible proposal location. The park being next to Navy Pier means it is right on the water giving you an amazing close up view of the city. The park has a few spots with this close up view of the Chicago skyline that are perfect for when you propose, and with the smaller scale of the park it means you’ll spend less time walking around to different locations for the rest of your session. This park packs a lot to love in a small space, for a full view of what a proposal looks like at Milton Lee Olive Park head to my blog post about one here! 

Henry Palmisano Park

Formerly known as Stearns Quarry, Henry Palmisano Park is the coolest little park located in the Bridgeport community.  The quarry that’s now become a park for the community is an incredible spot that feels almost completely removed from the city. There are some great scenic locations in the park like the fishing pond, a small waterfall/river leading to the pond, and the mound with a view of the city skyline that you can hike to the top of. This adorable park is a perfect spot in Chicago for a more secluded and intimate proposal, 

Alfred Caldwell Lily Pool

This Lily Pool located in the Lincoln Park Zoo is the most amazing little oasis in the city. Alfred Caldwell Lily Pool is completely surrounded by the beautiful trees and greenery of the zoo and is completely secluded from the city, even though it is basically in downtown Chicago! The Lily Pool itself is absolutely gorgeous and is such a romantic spot for a proposal. Being in Lincoln Park is also a huge benefit to the location as there is SO much nearby that we can walk to and enjoy for the rest of your session.

Honeycomb at Lincoln Park Zoo

Last and DEFINITELY not least we have the Honeycomb which is also located inside the Lincoln Park Zoo. The Honeycomb is a part of Lincoln Park’s nature boardwalk and one of it’s main attractions. The structure has an incredible view of the Chicago skyline and the greenery of Lincoln Park which make it an ideal spot for a proposal. The spot is one of the more popular locations within the Lincoln Park Zoo so plan on having some other people around during your proposal if you plan on going during peak hours. 

As you can see Chicago really is full of beautiful and unique spots for you to propose to the love of your life. Find a spot that means something to both of you or that you both enjoy and start planning out exactly how you plan to propose. I have a whole blog post about planning your own epic proposal which you can check out here, and if you need a photographer for your proposal head over to my contact page here!