Look no further! As a Chicago proposal photographer, I put together a list of my most requested and personal 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 backgrounds around the city to private-feeling nature-filled areas. 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.
1. North Avenue Beach
North Avenue Beach is my top requested proposal location in Chicago!
North Ave Beach is 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 at North Ave Beach 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
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.
In the summer, there are definitely lots of proposals at Olive Park as well as wedding photos, especially on weekends, so if you’re wanting a more private location, keep scrolling for different Chicago proposal ideas.
3. Grant Park
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. After your proposal, take pictures with the holiday lights, in front of Cloud-gate (aka The Bean), on the ice rink, or mosey over to Christkindlmarket and enjoy hot chocolate and mulled wine + pretzels for a cozy holiday date. Or, catch a view from above with a rooftop drink at Cindy’s Rooftop.
4. 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. 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, but I’ve had people propose here at all times of the year!
There are so many great photo ops with the bridge overlooking the pond, the honeycomb, or one of the parts of the walk that go off to the side a bit to have a slightly more private moment. This is an especially great location for a fall proposal in Chicago!
5. Alfred Caldwell Lily Pool
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
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, 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 if you’re looking for holiday lights and a big tree.
The lighting is almost always perfect at Wrigley Building no matter the time of day, but crowds can be a bit of a battle, especially in the summer and nice weather days, so it does require a bit of flexibility.
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! (Lincoln Park Conservatory too).
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 also host free spring flower shows, which is an even more fun burst of color as we transition into the spring months. If you want to avoid the cold, potential rain, or just love the look of being in a landscape we can’t find elsewhere in Chicago, the conservatories are some of the best places to propose in Chicago!
It can definitely get crowded on weekends, and you do need an online reservation (free) as well as a photography permit (around $85). You can book both of those here.
9. 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–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!
I’m Alana, and I’ve helped plan tons of proposals across Chicago and beyond, helping with the perfect location, timing, securing permits, and making sure we get all the meaningful moments on camera, without your partner suspecting a thing.
You’ll get a gallery of all the photos edited in my style with any basic distractions removed, all within 3 days of proposing to make sure you have your moments to share with everyone asap!
Inquire here for more details and availability, and let’s start planning your Chicago proposal!