Iconic Chicago Surprise Proposal Locations



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Guides + Advice, Proposals

Popping the question soon? Chicago offers so many iconic locations for surprise proposals! As someone who’s seen a lot of them, I’m bringing your my top three favorite proposal locations in Chicago. Let’s dive into these iconic Chicago surprise proposal locations.

LOCATION ONE – River Point Park | The underrated one

River Point Park actually opened in 2017, but I still don’t see a lot of surprise proposals and photos being taken in this location. I love this spot because it looks East, towards the lake, and has a great river view. There is easy access to the park off of Lake St, and it’s relatively quiet during the early evening hours on weekdays. Gibsons Italia and Beatnik are within walking distance and are great spots to have dinner reservations for after you propose. If you love the total Chicago look we can get with the El tracks and the loop, this may be the perfect place.

Hiring a photographer for your Chicago surprise proposal will ease your stress on planning and figuring out all the little details.

LOCATION TWO – North Avenue Beach | The skyline one

This is one of the most iconic proposal spots in Chicago! That view is something you can’t get anywhere else in the city unless you’re on a boat. There are other skyline view locations; this one feels the best because the city is still very close. Things to keep in mind for this spot are crowds; if it’s nice, there will probably be a lot of people out. If we plan for early Spring or late Fall, it’s likely to be windy and cold. That’s not enough to deter me from ranking it number two on this list, though. Parking is accessible using the lot attached to the beach with easy walking access or you can park for free along Stockton Drive by Lincoln Park and enjoy a walk.

beautiful engagement photos at north avenue beach
North Avenue Beach Engagement photographed for Victoria Saint Martin

LOCATION THREE – Lincoln Park Boardwalk | The pretty one

The Lincoln Park Boardwalk is an incredible location for a surprise proposal. I love how many options this spot has a lot to offer. City views are available from the South Pond bridge, the “Honeycomb,” and walking paths adorned by wildflowers in the Summer. You can park for free off of Stockton or utilize two different lots. The boardwalk can get busy, especially on nice days; during the evening and cooler days, it gets a little less crowded.


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