Being a Chicago native, I’m a little biased when I say that The Windy City is prime proposal real estate. I grew up there in the Midwest where the land is flat and the accents soft and I have to say, it is a storybook setting for the telling of any love story. The skyline is beautiful by day or night, from up close or far away, in the snow globe-like winters or picturesque summers.
Read on to hear about HowTheyAsked’s favorite Chicago marriage proposal ideas and some of my personal favorite spots.
Chicago Public Library
A quiet and private option: pop the question in a sea of dusty books. Hide the ring near one of her childhood favorites, bring your own hollow book safe, or simply drop to one knee in the check-out line. Be prepared for some excited whispers of congratulations.
This famous Chicago landmark is begging to be photographed. Bring your girl for an afternoon stroll, a photo-op at the Bean and later to the perfect proposal. Be sure to check out our vendor guide to find proposal photographers in Chicago.
Ask the big question here and make sure she knows that she is the only fish in your sea.
A Snowy Outdoor Proposal
Take advantage of Chicago’s winter wonderland and pop the question outdoors. Chicago’s Botanical Gardens is my top suggestion if you’re going the ‘under the open skies’ route.
Ask for her hand with the famous Chicago skyline as your backdrop. Aiming for something a little quieter? Any of the Evanston beachfronts are good candidates. Wait until dusk and you’ll get your yes to the faint glow of the city lights.
Videographer/Editor: Joe Bobbe, Plan A Productions
Photos by Dana Ann Photography
Spend some time under the stars and then take her outside for a lakeside proposal. Romance levels? Running high.
Choose any one of Chicago’s many forest preserves and set up a couples photography shoot. Drop to one knee in the middle and capture all the smiles and tears. Foolproof, we tell you.
Be sure to send us your Chicago proposal stories and photos. I’m all about that Chicago pride.