Lupe + Xiomara | Humboldt Park
Planning a Fall Proposal in Chicago’s Humboldt Park
If you’ve ever thought about proposing in one of Chicago’s most scenic parks, Humboldt Park in the fall might be the perfect spot. But, this wasn’t just another beautiful Chicago park, it was where they their connection first grew. This proposal blended sentiment, surprise, and Chicago’s golden autumn charm into one unforgettable day.
Is Humboldt Park A Good Location For A Fall Proposal?
What makes Humboldt Park a romantic proposal location?
Humboldt Park is one of Chicago’s most picturesque city parks, especially in late October when fall colors transform the park into a golden canvas of reds, oranges, and yellow. The sprawling lagoon, willow trees, and historic boathouse provide a mix of nature and architecture that feels uniquely Chicago. Nearby, the Formal Gardens at Humboldt Park add another layer of beauty with their seasonal flower beds, stone walkways, and historic design inspired by European landscapes. In the fall, the gardens glow with warm colors and create an elegant setting for engagement photos or a quiet walk after saying 'yes.'
Whether you’re planning a proposal surrounded by soft autumn light or under the canopy of changing leaves, this park offers plenty of privacy and personality.
When is the best time to propose at Humboldt Park?
Late October is an ideal time for a fall proposal in Chicago. The temperatures are cool but comfortable, and the sunlight filters beautifully through the orange and amber leaves. The park’s willow trees drape gently over the lagoon, adding a romantic touch — and if you’re lucky, you’ll catch reflections of the boathouse shimmering on the water.
Planning a Surprise Engagement Proposal
How did Lupe plan the proposal?
As locals who live near Humboldt Park, Lupe wanted the proposal to feel natural and meaningful. The setup began with a casual weekend brunch and coffee date at a nearby cafe. From there, he used the idea of stopping by The Hi-Lo for happy hour later as a reason to take a walk through the park beforehand.
This simple plan led them to the north side of the Humboldt Park lagoon, near an overlook facing the boathouse. This was the same area where they had some of their earliest dates, back when Xiomara was first showing Lupe around her neighborhood as someone from the suburbs.
How to plan a Proposal at the Humboldt Park Boathouse Lagoon
How did the proposal unfold?
As they walked along the lagoon path, the fall leaves created the perfect fall background. The sun was beginning to set, giving that golden hour look we all love. Lupe guided Xiomara toward the outlook near the lagoon with the boathouse framed in the background.
This is when the moment became perfect to pop the question. He took her by her hands, and began to share some loving words with her. As he dropped to one knee to propose, I was tucked away along the walking path, capturing every moment from a distance so the two of them could share this private and emotional moment together.
Of course, Xiomara said yes! After giving them a moment to soak it in, I joined them to congradulate and celebrate with a portrait session. Again with the fall colors, golden trees, reflective water, and a Chicago sunset you couldn't have planned it any better.
Why Humboldt Park is Perfect for Fall and Summer Proposals
Is Humboldt Park a good photo location?
Between the boathouse, nature paths, and lush lagoons, Humboldt Park offers a blend of nature and city aesthetic. The native plants and lagoons make it feel like an escape from the city even though it’s right in the heart of Chicago. It’s one of the few parks where you can get neighborhood vibes and nature-filled moments within the same walk.
Whether you’re planning a private fall proposal like Lupe and Xiomara’s or a summer engagement surrounded by greenery, the park’s versatility makes it ideal for year-round photography.
What To do After A Proposal
After the excitement of the proposal and portraits, Lupe and Xiomara wrapped up their day with a romantic dinner at Piccolo Sogno, one of Chicago’s most beloved Italian restaurants. It was the perfect ending to their day!
How to Plan a Proposal at Humboldt Park
Thinking about proposing at Humboldt Park?
Here are a few quick tips to help you plan:
Scout the location ahead of time. We can find a nice scenic area and vantage point, or keep it at a location thats special and meaningful to your two. Its also a great opportunity to check out the foot traffic and privacy of the area. depending on the time of year different areas of the park might be busier than others. The north side of the lagoon near the boathouse offers a stunning backdrop.
Timing is everything – golden hour (about an hour before sunset) gives that warm, cinematic glow. Early morning or late evenings are also a great times to consider.
Bring meaning into the plan. If you and your partner have memories in the neighborhood, incorporate them. Authentic moments always make the best photos. Or you can create new ones by planning a picnic date or day spent at one of Chicagos many parks.
Consider professional photography. I'm here to help with the planning and coordination to help ensure your proposal goes as smooth as possible!
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