10 Best Places to Propose in Chicago (2024)

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by Suzanne Sachs  5 min read



Chicago, Illinois is full of perfect places to propose. Whether you and the person you love are enthusiasts for gardens, parks, beaches, art, or good food and wine, there’s a beautiful spot to create a lifetime of memories. This guide describes some of the best places in Chicago to ask that special woman or man to marry you.


In this guide, we will explain the following:

  • Romantic Locations in Chicago for Outdoor Lovers
  • Chicago Botanic Garden
  • Buckingham Fountain
  • Millennium Park
  • Chicago Riverwalk
  • Sky Deck Chicago - Willis tower
  • Lincoln Park Conservatory
  • 360 Chicago
  • Romantic Destinations in Chicago
  • Adler Planetarium
  • Wrigley Field
  • Montrose Beach
  • Best Places to Propose in Chicago

Romantic Locations in Chicago for Outdoor Lovers


1. Chicago Botanic Garden

Located just outside the city, the Chicago Botanic Garden features beautiful gardens, including the Rose Garden and Japanese Garden, which are perfect for a romantic 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. It provides a picturesque and romantic backdrop for your proposal.


3. Millennium Park

The iconic Cloud Gate sculpture, often referred to as "The Bean," in Millennium Park is a popular spot for proposals. Its reflective surface provides a unique and artistic backdrop.


4. The Chicago Riverwalk

Stroll along the Chicago Riverwalk, which features scenic river views, restaurants, and beautifully landscaped areas. Find a quiet spot to pop the question.


5. Skydeck Chicago - Willis Tower

Propose with a breathtaking view of the city from the Skydeck observation deck on the 103rd floor of the Willis Tower. The panoramic vistas make for a memorable and romantic setting.


6. Lincoln Park Conservatory

Find a tranquil and enchanting spot at the Lincoln Park Conservatory. The conservatory is home to a stunning collection of exotic plants and flowers from around the world. Its lush and vibrant greenery, colorful blooms, and serene water features create a visually captivating and romantic setting for your proposal.


7. 360 Chicago

360 Chicago offers stunning 360-degree views of the city skyline and Lake Michigan from its observation deck on the 94th floor of the John Hancock Center. The breathtaking vistas provide a romantic backdrop for your proposal. The atmosphere at 360 Chicago is elegant and sophisticated, making it a fitting setting for a romantic proposal.


Suzanne was amazing! I utilized the layaway service and it was a breeze. Ring made its way to Texas and was even more gorgeous in person."
 Chloe G verified buyer

Romantic Destinations in Chicago

Chicago is full of romantic gardens, beaches, and parks. These are some especially romantic locations for a proposal over a glass of wine, a spectacular garden, or at a beautiful beach.


8. Adler Planetarium

The Adler Planetarium offers breathtaking views of the Chicago skyline and Lake Michigan. Consider proposing on the outdoor terrace, especially during sunset. The Adler Planetarium is situated on the lakefront, offering stunning and unobstructed views of Lake Michigan and the Chicago skyline. The backdrop of the serene lake and the iconic cityscape creates a visually captivating and romantic setting for your proposal.


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

9. Wrigley Field

If you and your partner are baseball fans, consider proposing at Wrigley Field, home of the Chicago Cubs. You can arrange for a special message on the scoreboard or a private tour of the stadium.


10. Montrose Beach

If you both love the beach, Montrose Beach on Lake Michigan is a picturesque location for a proposal, especially during a sunrise or sunset.


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.


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

Suzanne has always believed vintage rings can change lives. She's been in the jewelry industry for over 35 years, working with vintage jewelers, diamond dealers, diamond cutters, and gemologists. Suzanne started Artdecodiamonds in 2000 and understood the demand for vintage rings throughout the world. She ultimately started VintageDiamondRing.com in 2014, and understands each vintage ring is a reflection of you – your history, your relationships, your style, your elegance and is honored to have the opportunity to help you showcase your flair in a unique and exquisite way.
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Contact Suzanne

If you love vintage or eco-friendly jewelry please feel free to contact Suzanne or browse our collection of eco-friendly vintage engagement rings.


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