Here is our guide for planning the perfect Milton Lee Olive Park proposal. Whether you’re a local, or visiting Chicago for the weekend, Milton Lee Olive Park has one of our favorite skyline views. If you want the lakefront and beautiful Chicago skyline in your photos than Milton Lee Olive Park is the perfect choice for your proposal.

Best Season to Propose at Milton Lee Olive Park

Milton Lee Olive Park it is a true showstopper no matter what time of year, because you have Lake Michigan and the Chicago skyline as your backdrop.

We have photographed proposals at Milton Lee Olive Park in all seasons and can honestly say there is no wrong choice.

Spring/Summer

Spring and Summer are great options if you want the weather to be warmer. The leaves fill in on the honey locust trees that line the entranceway into Milton Lee Olive Park.

If your partner is one that doesn’t tolerate the cold then spring or summer could be great option for your proposal.

Fall

Even though the park’s main draw is the lakefront and skyline views, it does have some beautiful honey locust trees that change into a yellow color in the fall. If you want to see fall foliage then October might be a month to consider.

Winter

Proposing during winter does have some great benefits. Scenic locations like Milton Lee Olive Park are often busy during the warmer months with wedding couples, photographers, locals and tourists. During the winter, there are very few people at the park and it can provide more privacy for your proposal moment.

For Derek and Raechel’s proposal in December we were the only people in the park. The lake froze over and it provided such a unique backdrop for their proposal.

Best Time and Day for your Milton Lee Olive Park Proposal

Milton Lee Olive Park is open daily from 7 am to 8 pm. The best time of day for your Milton Lee Olive Park proposal is 1.5 hours before sunset. The lighting is ideal at this time for photos. This means that we might need to start the session as early as 3 pm in the winter months or as late as 6:30 pm in the summer months.

We highly recommend proposing Monday through Thursday instead of a weekend. Milton Lee Olive Park is such an iconic location and is popular amongst locals and tourists. The park is heavily visited on weekends by couples and photographers taking their engagement and wedding photos.

One added benefit to a weekday proposal is that your partner might be less suspicious. If you want to go out to a nice dinner after to celebrate, it will be much easier to make a reservation on a weeknight versus a weekend.

And if you have found the perfect photographer to capture your proposal, chances are they will be far more likely to be available on a weekday. Our weekends tend to book up quickly with weddings.

Favorite Proposal Spots at Milton Lee Olive Park

Milton Lee Olive Park has so many great options for your proposal. One of our favorites is the observation deck that extends out over the lake. This location has both lakefront and skyline views that are perfect for your Chicago proposal.

Another favorite is any spot in the park that is in the grass near the water with the skyline behind.

There are some more open grassy areas on the other side of the park that could be a great option as well.

Tips for Proposing at Milton Lee Olive Park

Here is some great advice for proposing at this iconic Chicago location.

1. Find a photographer.

Don’t find just any photographer, but one that has experience photographing proposals. We like to think of proposals as almost like a wedding in that there are no redos if you miss the moment. That makes it even more important to choose the right photographer for your Milton Lee Olive Park proposal.

2. Visit Milton Lee Olive Park before your proposal.

We understand that if you are from out of town this might not be possible. But if you have time on your trip to sneak away or are a local, then visiting Milton Lee Olive Park is a great idea.

This will help ease your nerves so that you don’t have to worry about getting lost. It will also make you feel that much more confident going into your proposal since you’ve been there before.

3. Come up with a cover story.

If you want the proposal to be a surprise then think about some ideas for why you and your partner are going to the park.

Maybe it’s somewhere you go to often on walks and chances are your partner won’t suspect a thing.

Or if you two love to go on picnics for date night then maybe suggest Milton Lee Olive Park for your next stop.

If you’re from out of town, mention that a coworker told you about an amazing Chicago spot with great views that you should checkout on your trip.

If you’re a Chicago local and don’t go to Milton Lee Olive Park then think of an excuse. We had one of our clients tell his significant other they were going to a holiday work party at Navy Pier. She got all dressed up and didn’t suspect a thing!

Get creative and don’t be afraid to ask your photographer for ideas. We’re here to help!

4. Share your location with your photographer!

An hour before your Milton Lee Olive Park proposal, start sharing your location with your photographer (if you have an iPhone). This is a great way to lessen the back and forth communication that day. You don’t want your significant other to get suspicious.

Regardless, make sure to text your photographer when you are 15 minutes away and again when you arrive at the park. Sometimes the location sharing doesn’t update right away and we don’t want to miss your arrival.

How to get to Milton Lee Olive Park

Milton Lee Olive Park is north of Navy Pier and next to Ohio Street Beach and Addams Park. The park is near the intersection of E Grand Ave and E Ohio St. You will see Lake Point Tower Condominiums across the street.

With Navy Pier and Ohio Street Beach nearby parking can be difficult. We highly recommend taking an Uber or Lyft to Milton Lee Olive Park.

Just put Milton Lee Olive Park into your GPS. You will get dropped off nearby the park, but will still need to walk a short distance to the entrance of Milton Lee Olive Park.

You will know you are in the right place when you see a black iron gate with a sign.

If you’ve never been to Milton Lee Olive Park before, it can be a little tricky to find the entrance once you get dropped off. See map above for walking directions.

Are you ready to propose at Milton Lee Olive Park?

Whether you’re a local or visiting Chicago for the weekend, we communicate every step of the way so that you can truly enjoy every part of your proposal experience. Through location guidance and great communication, we’ll help make this moment even more special than you envisioned.

Are you planning a Milton Lee Olive Park proposal or proposing elsewhere in Chicago? Click here for more info.

Contact us today!