Planning to propose to your partner and wondering "what are the best places to propose in Chicago?"


Look no further! As a Chicago proposal photographer and wedding photographer, I put together a list of my top, most requested, favorite locations for a Chicago proposal, along with tips for each spot. There are more than enough great locations to propose in Chicago, from iconic skyline views to Christmas tree background to private-feeling nature-filled areas. Keep reading to find the best Chicago proposal location!

1 . North Avenue Beach

man in green sweater on one knee proposing at North Avenue beach with Chicago skyline behind them

North Avenue Beach Proposal - where to propose in Chicago

man smiling and laughing with fiance after proposing at North Avenue Beach in Chicago
man in green sweater and woman in tan leather jacket hugging looking at the Chicago skyline at North Avenue Beach

North Avenue Beach is the most popular spot to propose in Chicago! At least for my clients :) It's the classic Chicago skyline look, and shows off the lake and the city all in one. It can be a bit chilly and windy in the winter, but it's still a beautiful view at all times of the day, in sunshine or clouds, winter or summer. It can range from a small "congrats" from someone walking by to the whole beach full of volleyball players cheering you on after, so if your partner prefers something more private, this *might* not be the place for you.

2 . Olive Park

woman in leopard print dress smiling with hand over mouth as boyfriend kneels down with ring for Olive Park Proposal

Olive Park Proposal - Where to Propose in Chicago

Another iconic location to propose in Chicago is Milton Lee Olive Park. Located right on Ohio St. Beach, there are opportunities for another angle of the Chicago skyline, along with a cute little beach, a tree-lined path, and a grassy area perfect for a post-proposal picnic. This spot is a little more public and definitely popular, so if you're a couple who likes the spotlight on them, this is a great spot! Otherwise, maybe opt for a different spot on this list.

3 . Grant Park

Man proposing to woman at Grant Park in front of Christmas Tree in Chicago winter

Grant Park Proposal - Where to Propose In Chicago

If you want to feel more immersed in the city rather than see if from afar, Grant Park is the perfect place to propose in Chicago. If you time it correctly, you'll get the perfect sunset behind you, or The Grant Park Christmas Tree during the winter, making Grant Park one of the best places to propose in Chicago in winter. After your proposal, take pictures with the holiday lights, in front of Cloud-gate (aka The Bean), or mosey over to Christkindlmarket and enjoy hot chocolate + pretzels for a cozy holiday date. If you're wondering where to propose in Chicago that wouldn't give it away, this is one of my favorites, especially if you're from out of town! Or, catch a view from above with a rooftop drink at Cindy's before your Chicago winter proposal.

4 . Lincoln Park Nature Path

dark haired woman proposing to girlfriend in Lincoln Park Nature Boardwalk with Chicago skyline behind them

Lincoln Park Nature Path Proposal - Where to Propose in Chicago

Another popular location for Chicago proposals is Lincoln Park Nature Path, specifically the "honeycomb" or bridge over South Pond. This is a wonderful location if you want a more low-key proposal. Just go for a walk, stop in the middle, and set up a sneaky photographer to get a picture. This is a great location to propose in Chicago during the warmer months when there is some greenery around, plus you can see the city skyline in the background. The bridge over South Pond is a better view of the city for a very Chicago proposal, and is beautiful year-round (although a bit chilly)!

5 . Alfred Caldwell Lily Pool

3 images of man proposing at Alfred Caldwell Lily Pool and woman happy crying with family

Alfred Caldwell Lily Pool Proposal - Where to Propose in Chicago

Located right next to Lincoln Park Conservatory, the Alfred Caldwell Lily Pool is the perfect private place to propose in Chicago. Although it's still outdoors and technically not "private," it's a much quieter, emptier place to take a quick, quiet walk amongst the lilies, enjoy the sounds of nature, and feel like you escaped from the city for a little bit. After your proposal you can hop right on Lakeshore and head down to a fancy dinner in downtown Chicago, or take a longer walk through the paths that connect you to LP Conservatory and eventually make it to the Nature Path.


Heads up, a permit for photography is required here.

6 . Wrigley Building

Wrigley Building Proposal - Where to Propose in Chicago

One of my personal favorite locations to propose in Chicago (or take engagement photos) is the Wrigley Building. This is a year-round favorite due to beautiful views of the building itself, plus right next door overlooking the Chicago River. Summer brings green trees, bright blue water, and of course the city in the background, while winter brings another grand Christmas tree, big red bows, and holiday lights, making this one of my favorite places to propose in Chicago in winter, especially if you're trying to avoid the crowds at Grant Park.

7 . Private Venue

In-home Private Proposal - Where to Propose In Chicago

If you're not interested in a public location for a Chicago proposal, check out a quiet restaurant like Travelle at The Langham, grab some rooftop drinks at one of the many rooftop bars in Chicago, including Raised, Londonhouse, and Cindy's, or propose in your home--you can always plan a photoshoot for the evening after your proposal if you want to keep it private, or ask your photographer for more personalized ideas!

Want some help planning the perfect Chicago proposal?


Hiiii! I'm Alana, and I've helped plan tons of proposals across Chicago and beyond, helping with the perfect location, timing, and even coming up with the backstory so your partner doesn't suspect a thing.


Inquire here and let's start planning your perfect Chicago proposal!