Best Places to Propose in Chicago

With Valentine's Day right around the corner, essentially National Engagement Day, I thought it would be kind of fun--and hopefully helpful--to do a round up of my favorite Chicago engagement spots.  These spots range from iconic, to slightly off the beaten path, but all equally amazing to pop the question.  They are not ranked in any order because I think they are all equally stellar.

Let's get started.

1. LondonHouse Chicago Hotel - 85 East Wacker Dr.

This place has got views on views and a champagne toast to boot!  The rooftop cupola is the perfect place to pop the question with both drama and intimacy, as the only people allowed up in the cupola are couples who have reserved the space.  If you happen to propose in the summer, you can even arrange to have a private meal in the cupola after the champagne has been drunk, the yes's have been repeated over and over, and the views have been admired.  The staff at LondonHouse help coordinate the proposal with a flower petal path leading up to the cupola, an ice bucket complete with Dom Perignon and two champagne flutes ready to celebrate.  One thing to note is that there is a fee for renting the cupola, and you must reserve it in advance simply by calling the hotel.


2. Shedd Aquarium at Museum Campus - 1200 S Lake Shore Drive

It's no mystery why many Chicagoans love to propose in front of the skyline.  It's beautiful and significant, so what better compliment to your upcoming proposal, right?  There are many places in Chicago that boast, "Best view of the skyline!", but I have to say that one of my favorites resides steps away from the Shedd at the lakefront.  This location has everything an iconic Chicago proposal could hope for: the lake, the museums, the buildings, the beauty.


3. Olive Park - 500 N Lake Shore Dr.

Another GEM of a skyline location.  My favorite part about Olive Park is how secluded it is (and I am probably about to ruin that with this blog post, but sharing is caring).  It is one of the only places that is not touristy at all, because it is quite off the beaten path.  It has a platform that kind of juts out over the water, which provides an awesome perspective of the skyline that I am not sure you can find anywhere else in the city.  It is beautiful year round, but would be a great location for a summer sunset proposal.


4. Millennium Park - 201 E Randolph St.

Before my people go rolling their eyes, I'm not talking about The Bean, I'm talking about this little area riiiiiiigggggghhhhhttt here.  It's on the south end of the park and it's as though it were made for the perfect photo op for two people.  Not to mention, when you're done proposing, you can head on out to ANY of the numerous fancy steakhouses or sushi restaurants to celebrate your engagement!  You will already be dressed up after all.  Best part about Millennium Park?  No permit required.  If it is a particularly nice night you can stroll around the park or hang out on a bench and people watch.  No matter what, there's no doubt that Millennium Park is an iconic Chicago spot for you to get down on one knee.


5. The Riverwalk - 100 E Wacker Dr.

Things I love about the Riverwalk: it's along Chicago's famous river, it has great views of the iconic bridges and skyscrapers, it is lined with restaurants, and it is expansive so you can find a spot away from other people to pop the question.  If you're really prepared, you can call one of the restaurants along the river and have a bottle of champagne ready for you to celebrate!


6. Art Institute Gardens - 111 S Michigan Ave.

Last, but most certainly not least, I bring you the Art Institute Gardens.  I can't exactly call this a hidden gem, since it is literally on one, if not the, busiest street in the city, but let's say it's hiding in plain sight.  The Art Institute Gardens have everything, especially if you are looking for a romantic place that gives the illusion of being "outside the city", while literally being steps from one of the most famous art museums in the world.  The only caveat with the Art Institute is that it is open from about April to November, so if you love it, plan your proposal accordingly.


So there you have it, folks!  Just a few of the many places Chicago has to offer for your proposal, one more memorable than the next.

Readers who proposed in this awesome city--where did you pop the question?  One of the places listed above or someplace different?  Let us know in the comments!