If you're going to propose in Chicago, location and time is key.
Chicago is a beautiful city with millions of places to pop the question, which will make an amazing backdrop to your proposal but presents an issue in choosing a location: Too many choices. Anywhere you look in Chicago there's a chance you'll see an amazing backdrop but these six locations will give you just a bit of an edge if you go at the right time. If you don't know anything about me as a photographer, you probably don't know that I spent 2 years finding every instagram worthy location in Chicago I could find. From classics like Lasalle Avenue (where the Dark Knight faced the joker) to the incredible views of the river at London House Chicago, I will help you figure out just where and when is the best time to propose for ultimate views. Some of these locations are better off in the morning if you want to avoid having 8 million Chicagoans directly in the background of your proposal photos. Did I mention you need a photographer for your proposal? Trust me, it's worth having this moment preserved properly.
#1 London House Rooftop Bar
If you haven't seen or heard of this place, take about 5 seconds and search it on instagram. It's beautiful just about anytime of the day, though crowds are way lower in the winter. In the summer you may need to reserve a private space on the rooftop deck, but if you go there in the winter, it's usually too cold for crowds. There are space heaters up on the impressive rooftop, and you can always warm up afterwards with some of the food and drink options from the restaurant inside. What makes this spot particularly interesting is that it has not one, but three very different views of Chicago depending on where your proposing. The Cuppola is a classic and has views of the Prudential building on one side, and the Wrigley Building on the other side. Meanwhile if you stay on the deck you can face one of the best views of the river in Chicago, specifically at sunset. The colors just sing, and there is no way either of you will forget the views.
85 East Wacker Drive At, N Michigan Ave, Chicago, IL 60601
#2 Calder's Flamingo (Sculpture)
Personally, I still don't think this is a flamingo. That said, it's iconic Chicago and I love the red beams against the black glass buildings. If you come early in the morning, you can get sunbeams like in the attached photo and there will be less people. Nightime is also great because the sculpture is lit up and makes for a dramatic backdrop. Avoiding high pedestrian traffic or Saturdays is key here because people love this thing. Sunday's especially outside of the summer this area is usually very tucked away and feels semi-private. This is also less cliche than the bean so I would highly recommend this spot over anything in millenium park for your proposal.
50 W Adams St, Chicago, IL 60610
#3 Milton Lee Olive Park Waterfront
As someone who vastly prefers the John Hancock Building to the Sears tower, this is one of my favorite views. It's usually got photographer's doing engagement, wedding, or portrait sessions on weekends so my advice would be a weekday or a Sunday in Fall-Winter because it should be a little less crowded, but I've found it's never over packed either way. This is located right next to Navy Pier so you can pop the question the go get dinner or ride the ferris wheel right after you get the yes. The best time of day for a proposal here is going to be sunrise or sunset for colors, but nighttime provides a pretty amazing view as well.
1010 E Ohio St, Chicago, IL 60611
#4 Chicago Theatre
You're going to have to fight this one out, there will be a crowd of people here all the time. It won't be super intimate, but it's a classic. Personally I have always felt that this spot is best captured with snow, which coincidentally will weed out crowds a bit as well. You could opt for a different view of the sign itself and propose at the CTA stop, but then you run the risk of the CTA agents ruining your proposal and yelling at your photographer for taking photos there. (They're super fun guys, let me tell ya...)
175 N State St, Chicago, IL 60601
#5 360 Chicago
Another classic, that I greatly recommend doing earlier than later. The crowds will be less active on weekdays in the mornings, while the colors will always be best at sunrise or sunset. You could ask to have a private event there for sunrise, I'm not totally positive on the rules or cost. The views are to die for just about anytime of the day, but be prepared for a lot of clapping when you get the yes if you didn't rent it out. Who doesn't like a little congratulations after asking though? Better colors: sunrise/sunset but you would be absolutely fine mid-day here and as a bonus it's indoors! Head back to the lobby and then go up to the Signature Room (or propose there during lunch/dinner) for some awesome food in addition to the views. Plus, then you can't argue about where to eat later!
875 N Michigan Ave 94th Floor, Chicago, IL 60611
#6 The Chicago Riverwalk
This is more of a catch-all proposal location suggestion, there are hundreds of spots I would recommend going to all across this river. The view in the photo is from wacker drive facing the Trump International Hotel and the Wrigley Building. The views are going to be gorgeous pretty much anywhere on the riverwalk, and it's super romantic. You could even propose in a wine igloo along the river at City Winery at the Chicago Riverwalk for the extra romantic vibes ( and some serious warmth those things are awesome!) I'd suggest that or walking to your favorite view and then grabbing a nice meal afterwards.
City Winery at the Chicago Riverwalk: 11 W. Riverwalk South, Chicago, IL 60601