#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 proposal location because it’s beautiful just about anytime of the day, though crowds are way lower in the winter. They even have a LondonHouse proposal package that covers decorations and prep. 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 Cupola 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

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#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 and there will be less people. Nighttime 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 cliché than the bean so I would highly recommend this spot over anything in Millennium Park for your Chicago proposal location.

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 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. This spot is located right across the street from Fight Club Chicago, it's called the The River Theatre. 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