Photo Chicago Proposal Ideas

Chicago Proposal Ideas

The 5 Best Chicago Proposal Ideas

As the nation’s leading proposal photography company, we know a thing or two about planning the picture-perfect Chicago marriage proposal!  We’ve helped countless couples plan and capture their engagement in the Windy City.


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Proposal With a View

One of the tallest structures in Chicago, the 1,729 foot Willis Tower (often referred to as the Sears Tower) offers incredible panoramic views of the Windy City.  Tell your special someone you want to take them to the observation deck to see your home city.  If you’re visiting from out of town, let them know that you want to capture a birds-eye view while you’re on vacation.  Once at the top, head to the observation deck to pop the question with amazing views.

Depending on your style and budget, you can make a reservation for two or reserve the entire Sears Tower Sky Deck restaurant.  There, you could have a meal for two either before or after your your partner says, “Yes!”

Sears Tower Proposal

Ben opted for a Sears Tower engagement.  Little did Jess know, he had one of our photographers capture the whole thing! View Ben and Jess’ engagement, here.


Bridge Proposal

The Kinzie Street Bridge is one of the most romantic and symbolic Chicago proposal locations.  The former railroad bridge has long since been shut down, and now remains in its upright position.  Nearby is a pedestrian footbridge with wooden slates and quaint red railings.  It provides a rustic touch set against the city’s modern architecture. Its views of the canal, the bridge, and the city beyond make it the perfect place for surprise engagement photography.

Kinzie Street Bridge Proposal

Corey and Erin’s Kinzie Street Bridge Proposal

Lake Proposal

Lake Michigan is the perfect place to pop the question!  Take advantage of the gorgeous views by planning your marriage proposal on the waters of the Great Lake.  Shoreside strolls and sunset sails provide the perfect opportunity to pop the question in warmer months.  In the colder months, arrange for a fancy dinner at a nearby restaurant to take in the views in comfort and style.


Park Proposal

Choosing your neighborhood park is always a romantic option for your engagement.  Add a horse and carriage ride, or head to a local jazz bar after for an impromptu surprise engagement party with friends and family.

But if you’re more for big gestures, or if you’re visiting from out of town, Millenium Park might just be the place for you.  Home to “The Bean” statue, this picturesque park offers a panoramic reflective view in the statue’s reflective surface.  Not to mention the nearby pathways provide incredible views.  It’s a great spot to stop and smell the roses, and have your surprise engagement shoot!

Millenium Park ProposalDaniel’s Cloud Gate Millenium Park Proposal

Baseball Proposal

Whether its the place you two shared your first date, where you’re at every summer weekend, or somewhere your partner’s always dreamed of going, Wrigley Field is sure to impress.  Home to the Chicago Cubs, the field is the perfect spot to knock your proposal out of the park.  Class it up by renting a table with bites and your favorite beverage (hot dogs and a good cold beer, anyone?).  Have your proposal message flashed on the big screen, and capture it all with a discreet surprise engagement photographer.

Helicopter Proposal

Surprise your special someone with a helicopter ride high above the city!  If the two of you are the adventurous type, or if you just want to see Chi-town from a different angle, hop inside a helicopter.  Ask for your partners hand thousands of feet above the ground for a unique and memorable marriage proposal.

Helicopter Proposal


Abdul’s helicopter proposal

We have planned and captured amazing Chicago marriage proposals and are ready to help you plan yours!

If all this Chicago proposal inspiration has you thinking about popping the question, reach out to one of our proposal experts for a free consultation.  We are here to offer local knowledge, proposal planning and surprise engagement photography, so that your “Yes!” moment is beautifully captured for years to come.