The 10 Best Places to Propose in Chicago


February 1, 2023

Planning to propose to your partner and wondering where the best place is to propose in Chicago?

Look no further! As a Chicago proposal photographer, I put together a list of the best locations for a Chicago proposal. There’s something for everyone, from iconic skyline views to Christmas trees around the city to a nature oasis. Keep reading to find where you should propose in Chicago, or scroll to the end to learn more about booking a proposal with me + what’s included (hint: it includes more personal help)!

1. North Avenue Beach

This is one of the most requested proposal locations in Chicago!

It’s a great all-in-one spot for a fabulous view of the skyline, the lake, sunset or sunrise, the city or beach, or a little bit of everything.

Proposals here can range from a small “congrats” from a passerby to the whole beach full of volleyball players applauding, so if your partner prefers something more private, this might not be the place for you. Summer tends to be busier, but on early morning or chillier days, you might get the whole place to yourself.

2. Olive Park

Another iconic location to propose in Chicago is Milton Lee Olive Park, located right on Ohio St. Beach. This is one of the only places in the city where you can see the sunset right behind the skyline, so it’s a top contender for sunset proposals! Plus the variety we have with the trees, the beach, and the city views is pretty unbeatable.

Similar to North Ave Beach, this location can get pretty crowded with other proposals and weddings in the warmer months, but there are tricks to work around it if you love the view like I do.

3. Lincoln Park Nature Path

Another popular Chicago proposal idea 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. People have proposed here in every season, but summer and fall take the cake. In the winter, you get the bonus of having zoo lights right nearby!

Choose from city views, wildflowers, or a little of each.

See a full session here.

4. Alfred Caldwell Lily Pool*

Located right next to Lincoln Park Conservatory, the Alfred Caldwell Lily Pool is a great alternative to other proposal locations in Chicago if you want something a little more private. Although it’s not entirely private, it’s a much quieter, secluded option compared to most other locations in the city. 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.

*Heads up, a permit for photography is required here.

5. Wrigley Building

One of my personal favorite places 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 or overlooking the Chicago River. The location is prime for visitors and locals alike for great photo ops, and it’s so central to all the delicious food and drinks the city has to offer for post-proposal celebratory libations. This is by far my favorite location for Christmas proposals in Chicago–call me basic, but this classic AF Christmas tree is the best in Chicago.

The lighting is almost always perfect at Wrigley Building no matter the time of day, but crowds can be a bit of a battle on warmer days.

6. Chicago Riverwalk

Just a few steps away from the Wrigley Building is the Chicago Riverwalk, another great proposal location! This is best at sunrise if you want to avoid crowds and lots of runners. Evening proposals are so fun to walk through the crowds and get applause from everyone if that’s your thing!

It’s the best in the summer when the trees are lush and the water is blue, but there are great photo ops here all year round with the classic Chicago architecture and trains behind you.

7. Museum Campus

Museum Campus has lots of options and locations within it, but most people go to the view from Adler Planetarium, then walk around to the Shedd, the Planetarium itself, or Field Museum.

This is a great spot to propose at sunset to still get the skyline in the photo, and of course we have a view of the lake in the other direction, or some beautiful architecture to play around with in photos.

You can even get tickets to one of the museums here for a post-proposal date idea, and some more photos depending on the venue’s rules at the time.

8. Garfield Park Conservatory*

If you’re looking for a lush, warm location (idea for cold, gray Chicago winters!!!), Garfield Park Conservatory is a great place to propose!

There’s a parking lot which makes driving easy, and there’s no shortage of fun spaces to take photos or propose. The palm room, fern room, and desert room are the most popular spots within, but there is truly a new photo op around every corner. Both GPC and LPC (below) also host free spring flower shows, which is an even more fun burst of color as we transition into the spring months. The conservatories are especially great options for avoiding bad weather in cold seasons or just as a backup plan.

Note: it can get crowded on weekends, and you need an online reservation (free) as well as a photography permit (around $85). You can book both of those here, or reach out to me and I’ll handle it for you.

See a full session at this location here.

9. Lincoln Park Conservatory*

This is similar to Garfield Park Conservatory above, but a little smaller. I prefer this location if you want to stay more central to the action that Lincoln Park offers. The Lincoln Park Conservatory consists of the fern room, palm room, and show room.

Zoo lights are a great winter date idea before a proposal since they’re next door. There are also lots of great bars and restaurants for engagement parties with all your friends and family nearby. A lot of my clients use this as a backup location in case of bad weather, or in winter when they want a little more color in their photos after an outdoor proposal.

Keep in mind the conservatory generally closes at 5pm, and last entry is 30-60 minutes before that.

*Permit required as well as a free online reservation

10. Private Venue

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, choose your first date spot and rent out at a room like at J9 Wine Bar, or propose in your home or another meaningful location. You can always plan a photoshoot in the days following your proposal, too, if you want the actual moment to be totally private.

Want more ideas? Check out recent proposals on the blog, or click on any of the locations above to see more photos in each spot.

Looking for a Chicago proposal photographer?

I’ve planned and photographed more Chicago proposals than I can remember–and each and every one is so much fun to be part of. I’ll help with all the details and keep it simple so you can focus on what really matters–not losing the ring 😉

Inquire here for more details and availability, and let’s start planning your proposal!

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