10+ Awesome Chicago Marriage Proposal Ideas

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.

Oh, and be sure to hire a photographer. We LOVE Flytographer (they have proposal photographers in 150 cities worldwide) but we have a list of other great proposal photographers in Chicago as well.

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.

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Read this Chicago Public Library Proposal // Photos by Aparna Paul Jain Photography

Millenium Park

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.

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See the Millenium Park Marriage Proposal // Photos by Peter Gubernat Photography

Shedd Aquarium

Ask the big question here and make sure she knows that she is the only fish in your sea.


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Read the Shedd Aquarium Marriage Proposal here // Photos by Keren Sarai Photography

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.

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Snowy Marriage Proposal in Chicago // Photos by Gray Photography

Lake Michigan

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.

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Videographer/Editor: Joe Bobbe, Plan A Productions

Lakeside Proposal

Downtown Chicago is filled with these lakefront open spaces. Perfect for picnicking, impromptu meet ups with friends and of course a magical moment like this lakeside proposal.

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Photos by Dana Ann Photography

Adler Planetarium

Spend some time under the stars and then take her outside for a lakeside proposal. Romance levels? Running high.

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See the gorgeous Chicago Proposal here // Photos by Peter Gubernat

Forest Preserve

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.

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Photoshoot Marriage Proposal // Photos by Cassandra Eldridge Photography

Be sure to send us your Chicago proposal stories and photos. I’m all about that Chicago pride.

Want more? Read 10+ disney proposal ideas, a ton of Christmas Proposal Ideas, or learn how to buy a diamond here!