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 HowHeAsked’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.

Chicago_Public_Library

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.

Millenium_Park

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.

Ba-dum-ch.

Shedd_Aquarium

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.

Snowy Proposal

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.

Lake Michigan

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.

Lake Michigan_2

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.

Adler Planetarium

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!