The Best Places to Propose in Chicago

If you’re getting ready to pop the big question then you’re probably wondering where you should do it. Thankfully Chicago has some amazing spots to get down on one knee for that big YES! Here are the five best places to propose in Chicago!

1. LondonHouse Chicago

The views from LondonHouse are easily some of the best in Chicago. From the main rooftop lounge you get an amazing panoramic overlooking the Chicago river that really comes alive at sunset. For a slightly more private proposal, you can head to the other end of the rooftop and propose in the cupola which overlooks Michigan Ave, including the Wrigley and Tribune Buildings.

Another reason why I love the LondonHouse rooftop for proposals is because it’s easy to keep your plans a surprise! It’s a natural spot for a date night or late lunch so it’s easy to convince your significant other to head up there without tipping them off! After the emphatic “YES!” stick around and celebrate with a drink … or a bottle of champaign (or two)!

LondonHouse Chicago

2. Milton Lee Olive Park

Milton Lee Olive Park is like your front row IMAX seat to the Chicago skyline. The buildings rise like a beautiful wall of glass and steel overlooking the park – particularly the Hancock Bldg. It’s a classic spot for wedding and engagement photos as well, which means your proposal photographer will blend right in without tipping off your partner with what’s about to happen.

If you’re wanting the place more to yourself, show up at sunrise and you’ll get some amazing light. However just like with LondonHouse, sunset is going to be the best time of day to really take advantage of the beauty of this location. Plus afterwards you can take the short walk over to Navy Pier and celebrate with dinner, drinks, and even fireworks on a Wednesday or Saturday evening during the summer.

3. North Avenue Beach

Another classic Chicago location, and hands down one of my favorite places for any photo shoot, is North Avenue Beach. The unique thing about this spot is the breakwater that extends out into Lake Michigan. It doubles as a walking and running path that provides opportunites for stunning views and unique photos.

Sunrise or sunset are equally great times for a proposal here as the light looks stunning here in either case. Afterwards you can walk back into the city and celebrate with brunch or dinner at any of the numerous restaurants in the area.

4. Alfred Caldwell Lily Pool

Tucked away on the north end of the Lincon Park Zoo you’ll find the Alfred Caldwel Lily Pool. Though still a popular spot, it gets a lot less traffic than much of the area around it and therefore makes for a super romantic and slightly more private location to pop the marriage question.

Since it is somewhat isolated and surrounded by trees, I suggest planning your proposal here about an hour or two after sunrise or before sunset just to be sure it isn’t too dark for great photos. Like with most of the locations on this list there are tons of great spots nearby to go celebrate after you get that big “yes”.

5. Garfield Park Conservatory

If you’re wondering, “where can I propose in Chicago in the winter?” and not freeze your a$$ off, then the Garfield Park Conservatory is your spot. It’s open and warm year round and on top of that, it’s stunning inside! They have a couple different greenhouse areas with different themes, some more tropical, other more desert.

If you’re going to have a photographer document your proposal, then be aware that either you or your photographer will need to get a permit. I handle this for my couples, but it’s pretty straight forward and can be obtained online fairly easily.

Drop in here mid to late afternoon, once the sun isn’t straight overhead, and you’ll find some amazing light that is perfect for your photos. This will also allow you time to head out somewhere downtown to celebrate as you probably won’t find too much in the immediate vicinity.

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