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  • Christina Hubeli

Creative Chicago Proposal Ideas


creative fall proposal ideas
Photo: AJ Ableman Photography

November to February is affectionately known as engagement season in the wedding industry, and you may be thinking about popping the question to your partner this season.


Like many of your soon-to-be-engaged Chicagoans, you want a fun, fresh, and personalized way to propose to your lover. Or maybe you’re needing to send this blog to your boo for a little nudge. Either way, read on for some of our favorite city proposal ideas, from simple to extravagant.


For the foodie couple:


It’s no secret Chicago is home to a wide range of delicious restaurants, from homey classics like Giordano’s to indulgent tasting menus like Alinea. Take advantage of the city’s food scene by taking your partner out to a tasty meal. The question of where depends on your style as a couple!


If you prefer dinner with a view, consider a dinner cruise along Lake Michigan, during which you’ll be treated to a classic 3-course meal with breathtaking views. Or, if you’re looking for a little more DIY, create your own food walking tour with a handful of stops that are meaningful (and yummy) to you as a couple. Consider a stop for drinks, apps, a main, and dessert.


Perhaps you prefer to keep things a little more low-key but still want to take advantage of the awe-inspiring Chicago skyline. Book a stay at one of Chicago’s iconic hotels; whether on the river or in the Loop, snag a room on a higher floor for the best views. Order in your and your partner’s favorite restaurant, pop a bottle of bubbly, and have a romantic dinner for two overlooking the city!


For the nature-loving couple:


Despite being a large metropolitan city, Chicago has so many nooks of beautiful and serene nature. Although the weather is starting to get chillier, the beach is still a stunning place to propose! (And am I the only one that thinks the lake still looks great when covered in ice caps?).


If you’re not a big fan of the beach, try out the Chicago Botanic Gardens. With 385 acres of land and 27 gardens, you’re sure to find the perfect spot to get engaged. If you prefer something a bit more intimate and hidden, the Alfred Caldwell Lily Pool is the spot for you. Tucked away from the hustle and bustle of Lincoln Park, it features a looping path, spots to stop and observe nature, waterfalls, and an eye-catching pavilion for popping the question.


For the Chicago-born-and-raised couple:

If you’re a Chicagoan looking to incorporate your love for the city into your proposal, you’ve got plenty of options. First head over to Navy Pier for a romantic ride in the iconic Ferris wheel. Then, take a stroll through Millennium Park, stopping at the Bean to get down on one knee! Celebrate after with a cake shake from Portillo’s.


Want to incorporate an experience into your proposal? Take your partner on a trip to Museum Campus for a visit to the Field Museum, Shedd Aquarium, or Adler Planetarium. You could propose in any of these, or walk out to Northerly Island Park after your visit for a proposal with a stunning view of Chicago.


If you want to avoid (some) tourists, consider other museums like the Museum of Science and Industry, the Chicago History Museum, or the Art Institute. Each one is conveniently located by a park with a gorgeous setting for your engagement.


For the couple looking to take it to “new heights”:


If you want to feel like you’re on top of the world during your proposal, the Willis Tower Sky Deck is the perfect place for you. (If you or your partner aren’t a fan of heights, you might want to skip this section). With gorgeous views day or night, you’ll literally be standing on top of the city during your engagement.


Or, kick things up a notch with a private helicopter tour! Fly around the city to get a birds-eye view of all the famous buildings Chicago has to offer. It’ll be a once-in-a-lifetime experience that you’ll never forget.



Proposing to your partner can be a bit intimidating! But with a solid plan that fits you as a couple, you’ll be on your way to a perfect proposal.


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