7 Best Places to Propose in Chicago, Illinois

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by Suzanne Sachs • 5 min read

THE BASICS --

Chicago, is full of perfect places to propose. Whether you and the person you love are enthusiasts for gardens, parks, rivers, fountains, lakes, or good food and wine, there’s a beautiful spot to create a lifetime of memories. But where, exactly, should that most important question be asked? This guide describes some of the best places in Chicago to ask that special person to marry you.

WHAT YOU NEED TO KNOW--

• Romantic Locations in Chicago for Outdoor Lovers
• Millennium Park
• Buckingham Fountain
• Chicago Riverwalk
• Sky Deck Chicago - Willis Tower
• Grant Park
• At Home
• Budget-Friendly
• Best Places to Propose in Chicago

Romantic Locations in Chicago for Outdoor Lovers

1. Millennium Park

The iconic Cloud Gate sculpture, often referred to as in Millennium Park is a popular spot for proposals. Its reflective surface provides a unique and artistic backdrop. The park is home to the famous Cloud Gate sculpture, also known as "The Bean," which offers a unique and reflective backdrop for a memorable proposal. 

2. Buckingham Fountain

The iconic Buckingham Fountain in Grant Park is a classic spot for a proposal, especially when it's illuminated at night. The fountain is situated in Grant Park, offering stunning views of the city skyline, Lake Michigan, and the park's lush greenery.

3. Chicago Riverwalk

The Chicago Riverwalk is a vibrant and scenic promenade that stretches along the Chicago River, offering a unique and romantic setting for a proposal. The waterfront views, combined with the bustling city life, create a lively yet intimate atmosphere. Proposing here in the evening, with the city lights reflecting on the water, ensures a magical and memorable experience.

4. Skydeck Chicago - Willis Tower

Proposing at the Skydeck of Willis Tower is an exhilarating and unforgettable experience, perfect for those seeking a unique and adventurous setting. As you step onto the glass ledge 1,353 feet above the bustling city, you'll be met with unparalleled panoramic views of Chicago, stretching out to the horizon.

5. Grant Park

Known as "Chicago's front yard," Grant Park is a sprawling green space that offers a beautiful and diverse backdrop for a proposal. The highlight of the park, Buckingham Fountain, is especially stunning during the evening light show, creating a captivating and romantic atmosphere.

6. At-Home

Sometimes the most heartfelt proposals happen right at home. In Chicago, transform your apartment, balcony, or backyard with twinkling string lights, a cozy dinner featuring deep-dish pizza or your favorite neighborhood takeout, and a playlist filled with local favorites like Chance the Rapper or classic blues. Add personal touches like fresh blooms, flickering candles, or even a warm fire pit to create an intimate, unforgettable moment that's all your own.

7. Budget-Friendly

A romantic proposal doesn’t require a luxury budget. Chicago offers beautiful and meaningful locations that are free or low-cost but still incredibly special. Stroll hand-in-hand along Lake Michigan at sunset, enjoy a breezy moment at Montrose Beach, or pop the question in the serene beauty of the Chicago Botanic Garden. For something more unique, toast with a local vintage at Lynfred Winery or plan a surprise proposal at iconic Wrigley Field. These unforgettable settings prove that love doesn’t need a big price tag to make a big impact.

“I've purchased two vintage rings from Suzanne over the past decade and my wife has loved both. Great service, communication and speedy delivery.”

— Lee S verified buyer

Best Places to Propose in Chicago

While it can be tempting to get wrapped up in elaborate proposal plans, sometimes the very best way to ask the question is a classic, heartfelt, on-one-knee moment. Whatever you and your soon-to-be fiance or fiancee enjoy, Chicago has beautiful and memorable places to propose. Make one of these romantic locations your special place by proposing with the perfect vintage engagement ring.

It's Time!

Chicago has so many beautiful places to propose—now it’s just about choosing the perfect one. Make the moment even more special with the perfect vintage ring—schedule a virtual appointment or email us to get 5% off when you purchase a ring and mention our Best Places to Propose in Chicago blog.

Vintage Engagement Rings For Everyone:

No matter which era is your favorite, these time-honored rings have a rich history and individualized character and will continue to have a timeless beauty and elegant appeal that is part of a legacy to pass on to future generations.

Find The Perfect Engagement Ring:

Vintage rings are prized not only for their beauty but also for their exquisite attention to detailing and faceting. If you’re looking for a ring with a sense of glamour, sophistication and vintage charm, explore our collection of vintage engagement rings today!

Suzanne Sachs