I’m planning to propose to my girlfriend in Chicago in June and could use some local opinions. She lives in the West Loop, and I’m somewhat familiar with the city, but definitely don’t know it well enough to feel like I’ve found every good option.
Right now, I’m considering Milton Lee Olive Park because it’s a place we’ve walked before and it would feel natural to end up there without tipping her off. I’d like the proposal to be private or at least semi-secluded, with a photographer nearby, and ideally somewhere we can get nice photos without a crowd immediately around us.
A few things I’m trying to balance:
- She loves surprises, so I want the outing to feel natural and not overly staged.
- I’m considering either a late-afternoon/evening proposal on a Thursday night.
Would you recommend Milton Lee Olive Park for this, or is it usually too crowded/exposed? Are there specific areas within the park that are more secluded? Also very open to other locations, venues, photographers, or itinerary ideas that people think would work well for a private-feeling Chicago proposal.
I truly appreciate your opinions here, thank you.