Where to Propose in Chicago: Hitched’s Top 5 Scenic Picks

By Kiersten Weed

Romantic Proposal Spots in Chicago

If you’re reading this article, chances are that you are getting ready to propose in the windy city and looking for the perfect spot! You’re in luck, because the Hitched Chicago team compiled a few picturesque proposal locations that make a special choice for your milestone.

Are you still looking for your engagement ring? Book a consultation with our Chicago team to discuss the best option for you!

North Pond Restaurant Proposal

This spot is perfect for the foodie couple. Get engaged and enjoy a delicious brunch or dinner after? Sign us up! The restaurant is surrounded by lush greenery and serene water, a great choice for a Spring or Summer proposal. Want to make the moment extra special? Invite loved ones to the restaurant for a surprise after the proposal is complete. Book your reservation here!

Photo via @northpondchi on Instagram

Navy Pier Proposal

Dreamy skyline view at sunset? Say less! The Navy Pier is a versatile spot you can propose at year round. Take a romantic stroll after you pop the question and meet up with friends and family at a nearby restaurant or bar for a post-proposal celebration!

Garfield Park Conservatory Proposal

If you’re looking for the ideal photo backdrop, this is it! Flowers, trees, fountains, and unique architecture make this a special spot to get engaged. Find a secluded spot to ask the big question, and easily hide a photographer to capture the moment. If you want the proposal to remain more intimate with friends and family, you can also rent out space at the Conservatory and celebrate with a party afterwards!

Photo via Management on Trip Advisor

Alfred Caldwell Lily Pool Proposal

Katie Cutcher, Assistant Manager of Hitched Chicago, describes the Alfred Caldwell Lily Pool as “right in the busiest part of Lincoln Park, but people don't know it exists, so it's really quite peaceful.” If that’s your vibe, then this is the spot for you! This location is serene and quiet, perfect for the person looking for an intimate proposal.

Photo via Lincoln Park Conservancy

Rooftop Proposal - The Robey

If you’re looking for a proposal with a view, you should definitely check out the Robey Rooftop Bar. Located in Wicker Park (right near our showroom!) it’s a great location for a chic city proposal. Celebrate with champagne after, and invite friends and family for an intimate party!

Photo via The Robey

Still Shopping For Engagement Rings In Chicago?

Now’s the fun part! Finalize your engagement ring and start prepping which date you want to propose. Make sure to book your photographer and make any reservations as far in advance as possible to ensure spots don’t get booked up. Happy planning!