The Best Chicago Engagement Locations in the City

April 14, 2021

If you’re going to get engaged you’ll need to know these Chicago engagement locations.

Chicago has about a million really great locations, which will make an amazing backdrop to your proposal but presents an issue in choosing an engagement location: Too many choices. Anywhere you look in Chicago there’s a chance you’ll see an amazing backdrop but these engagement 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 wedding 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 Chicago engagement locations are better off in the morning if you want to avoid having 8 million Chicagoans directly in the background of your engagement photos. Did I mention you need a proposal photographer for your proposal? Trust me, it’s worth having this moment preserved properly.

Chicago rooftop proposal photographer at London House Chicago

#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 is intentionally my number one Chicago engagement location because it’s beautiful just about anytime of the day, though crowds are way lower in the winter. In the summer or at sunset 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

Downtown Chicago proposal location Caulder Flamingo

#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

A picture of the John hancock from Milton Lee Olive Park Chicago Engagement Photographer

#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

Chicago Theatre during a snowstorm from a Chicago proposal photographer

#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 Chicago Riverwalk Engagement Photos

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

If you need indoor locations for your engagement photos, wedding venues during the week are always a great or one of the many hotels downtown.

BONUS locations!

Lincoln Park is amazing for engagement photos.

Union station in downtown chicago elopement
Union Station, though not free is incredible.

Union Station

The Axis Apartments Downtown if you have a friend there.
Navy Pier at sunst in Chicago
Navy Pier is very popular, but also beautiful.

An engagement location in Chicago on a yellow staircase.
This yellow staircase in chicago is kind of famous on instagram.
River North Chicago engagement photograph
River north is also great for engagement photographs.
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