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Inspiration » Proposal Ideas » The 14 Best Places to Propose in Chicago

The 14 Best Places to Propose in Chicago

by Joy Editors
The 14 Best Places to Propose in Chicago

As a “Windy City” nestled on the Southwest corner of Lake Michigan, Chicago is famed for its bold architecture, arts scene, and straightforward yet friendly locals. It’s a place where what you see is what you get, and what you see is extraordinary. Resting in the folds of this vibrant metropolis are magnificent displays of nature, man-made wonders, and havens for aquatic life, providing unique, romantic, and affordable places to ask those 4 sacred words: Will you marry me? To help you find the place that’s just right for you and your special someone, we’ve pulled together 14 of the best places to propose in Chicago that are sure to accentuate that sweet sound of yes as you enter the next stage of your romantic journey: wedding planning.

1. LondonHouse Cupola

Propose in style on the 23rd floor of the luxurious LondonHouse hotel, but make your way to the cupola which features towering Corinthian columns and jaw-dropping, 360-degree rooftop views of the city. One of the best places to propose in Chicago, it’s so popular that the hotel offers a proposal package including 1 uninterrupted hour in the cupola, a private escort to this astonishing location, a bottle of Dom Pérignon, a rose petal walkway, and a private dining room if the weather turns. This proposal spot provides stunning photo ops, so be sure to have a photographer waiting in the wings.

2. Chinatown’s Ping Tom Park

If you’re not keen on the idea of tourists witnessing your proposal, head to this majestic yet underutilized 17-acre park at sunset. If you time it right at Ping Tom Park, you and your love will experience an extraordinary view of the city skyline, and the adjacent Chicago River, glowing with ethereal pinks, oranges, and yellows to highlight your special moment.

3. North Avenue Beach

If you’re dropping to one knee in the summer, and have an affinity for sinking your soles in the sand, head to this lakefront beach. To sprinkle extra wonder on the momentous occasion, propose as the sun sets as this will create a mesmerizing reflection of the surrounding buildings twinkling on Lake Michigan. Because North Avenue Beach is so long, you can usually score some privacy if you don’t mind a stroll down the shore.

4. Navy Pier’s Centennial Wheel

Why not go for classic romance with a proposal at Navy Pier‘s Centennial Wheel? As a can’t-go-wrong romantic spot, one of this Ferris wheel’s transparent gondolas can take you 200 feet above the city, offering amazing views and a splash of thrill.

5. Cloud Gate, aka “The Bean

To craft a proposal photo that just might be the next viral Insta post, head over to Cloud Gate in Chicago’s Millennium Park. As you ask your love for their hand in marriage in front of the massive, stainless-steel bean, your reflection — and the engagement ring — will be cast across the surface of this iconic Chicago fixture. 

Tip: It’s a must to have a professional proposal photographer here, waiting to capture the happy scene.

6. Wrigley Field

If you and your significant other love sports (especially the Chicago Cubs), and don’t mind the limelight, pay the $200 fee to have Will you marry me? and a personal message displayed on Wrigley Field‘s massive message board during a game.

7. Buckingham Fountain at Night

Between early-May and mid-October, whisk your lover away for an evening rendezvous at the grand Buckingham Fountain in the center of Grant Park. Beginning at dusk, this proposal location dazzles with a 20-minute extravaganza of lights, music, and water displays, which includes a center jet shooting 150 feet into the air. The display starts every hour on the hour, with the last one beginning at 10:35 pm, creating many opportunities to proclaim your love at one of the best places to propose in Chicago.

8. Alfred Caldwell Lily Pool in Lincoln Park

Make your partner feel like they’ve landed in a fairytale by proposing beside this whimsical lily-covered pool, a hidden gem that was created in the late 1930s. As you walk on the stone path encircling the pond at Alfred Caldwell Lily Pool, you’ll come across some of the most romantic Chicago proposal spots such as a prairie-style pavilion and charming bridge. In addition, your big ask will be enhanced by the soothing patter of the pool’s waterfall.

9. Lincoln Park Conservatory Show House

If you want to craft a proposal that exudes the majesty of Mother Nature, but you plan to propose during one of Chicago’s many frigid months, head to this lush, indoor proposal destination. A wonderland of exotic plants, the Lincoln Park Conservatory Show House makes you feel like you’ve been transported to an enchanting jungle, even if there’s snow falling outside.

Tip: Go about an hour before closing to avoid the crowds.

10. Adler Planetarium

This public museum is a paradise if you have a passion for astronomy and astrophysics, allowing visitors to have an up-close and personal tour of the moon and stars. The Grainger Sky Theater, providing a 360-degree, simulated view of the cosmos, is the crown jewel of the Adler Planetarium and a prime place to pop the question.

11. Skydeck at Willis Tower

If you and your partner don’t mind heights, or you enjoy stepping out of your comfort zone (literally), the Skydeck at Willis Tower is a dramatic place to propose. Located on the 103rd-floor—1,353 feet high—of what used to be known as the Sears Tower, the Skydeck allows you to step into a glass box extending 4.3 feet from the building. For a proposal soaked in romance and thrill, assume the proposal position as you’re perched on what feels like the top of the world. (And don’t forget to take photos!)

12. Boka

Is your soon-to-be-fiancé a foodie? If so, head to this Michelin star eatery that’s been awarded this accolade every year since 2011. After feasting on dishes such as Shima Aji Crudo, Roasted Veal Sweetbreads, and Ricotta Dumplings, round out the meal by dropping to one knee. Then, celebrate by indulging in Boka’s famous Strawberry Pavlova.

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