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Best places to propose in Chicago

on June 16, 2023

The majestic windy city has everything any couple could wish for in the background of a marriage proposal: perfect natural landscapes, great lake views, tall buildings, luxurious private locations, cultural centers, art, light shows.

Best places to propose in Chicago


It's easy to get overwhelmed by so many great options, so we've decided to help the undecided a bit and create a list of the best proposal spots in Chicago.

Choose your favorite, get the right jewelry, and create an unforgettable story.


Getting engaged in chicago

Although there are hundreds of great locations we have chosen to separate them into four great options (favorites). A stroll through Chicago's most romantic locations in any season of the year, special attractions for the winter seasons, more private options for a night out that ends in an unforgettable proposal, and iconic locations.

As always, remember that the best of all options will always be the one that best matches your style, your partner's style and what you both consider symbolic.


Romantic places in chicago to propose

When it comes to romantic proposals we have three places that stand out by far. Each has incredible views and are easy to include in a weekend getaway to share as a couple and make an unexpected proposal.


Adler Planetarium

A real love, sincere and infinite as the cosmos. A beautiful idea that can be embodied in your proposal if you choose the Adler Planetarium, which brings visitors closer to space than any other place. The Grainger Sky Theater will create a 360° illusion of you, your partner and a universe of possibilities in your new life together.

Adler Planetarium


Navy Pier's Centennial Wheel

Few places become as beautiful at sunset as the Centennial Wheel.
A Ferris wheel high above, a panoramic view of the city as the sun goes down, an emotional, breathless question and a memorable memory that will bind you together forever.


Navy Pier's Centennial Wheel


Buckingham Fountain

The Buckingham Fountain light show in Grant Park is known throughout the country and is one of the most romantic nighttime settings for a proposal in Chicago, at least for the 20-minute duration of the show.

Make good use of the time, plan a spot away from the curious and the hopping.


Best places to propose in chicago Winter

The changing of the seasons is one of the first things to keep in mind when exploring Chicago proposal ideas. With the arrival of winter, lights, snow and festivities, some options that might once have gone unnoticed take on a renewed charm.


Maggie Daley Park

Maggie Daley Park


When it comes to winter entertainment in Chicago, the ice skating at Maggie Daley Park is a must-see. The setting is perfect for an entertaining couple's outing, full of Christmas lights and decorations, with plenty of great places to get down on one knee and pop the question.


North Avenue Beach

North Avenue Beach


North Avenue Beach offers a long walk along the edge of Lake Michigan, full of beautiful spots to propose in private, but not so far away from the vibrant metropolis that looms imposingly on the horizon, leaving the perfect setting for a few spectacular shots, even in winter.


The Grant Park Christmas Tree

The Grant Park Christmas Tree is an incredible place to propose in Chicago during the winter. Although this area is attractive year-round, the holidays bring with it a sea of twinkling lights, ornaments and a great trail full of architecture and art to appreciate before the perfect sunset with which to deliver a brand new diamond wedding ring.


Best restaurants to propose in chicago

The romantic ambiance is more about the details and the overall experience than the venues themselves, or at least it is for many. Those who enjoy an intimate evening and find a luxurious setting appropriate for such a proposal will find the best restaurants in Chicago the ideal setting.


Signature Room

Located in the imposing John Hancock Center, just off Michigan Avenue, is one of the most iconic locations in all of Chicago, at no less than 95 stories high: The Signature Room.

Signature Room


This upscale bar/restaurant offers one of the most breathtaking panoramic views in the city where you can take in the light show on the horizon, or if you prefer, make a statement in the last rays of the afternoon sun.



One of Chicago's top award-winning, Michelin-starred restaurants that has remained untouched year after year.

Complete an exquisite dinner with a romantic proposal in this unique and elegant setting.



Recognized three times as the best restaurant in the entire United States and winner of three Michelin stars, Alinea is the fine dining restaurant to aim for if you're willing to go big with luxury included.


Best landmarks to suggest in Chicago

Many times it's not about finding a beautiful venue, but a truly iconic one that everyone can recognize from a simple photo, especially when it comes to a Chicago wedding proposal.


The Art Institute of Chicago

The Art Institute of Chicago


One of the most representative temples of art in the world, not to be missed if you are in Chicago and to propose, of course, next to any of its hundreds of thousands of works and spaces of great architectural appeal.


Shedd Aquarium

The Chicago Aquarium is one of the most recognized and important in the world, full of interesting activities to enjoy as a couple and majestic scenery to propose, in view of its more than 30,000 aquatic species, ideal for taking dream photographs.


Lake Michigan

For those who are looking for a landscape that really says Chicago, a yacht or private boat that sails at sunset on Lake Michigan, with good weather, is one of the most perfect environments that can exist to propose.


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