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Wedding Ideas

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Best Places to Propose in Chicago

by Melia Dicker on Apr 10 in Proposal


This post is part of the My Trio Rings Precious Places series, which uses Mashable's Top 10 Cities for Getting Engaged list for inspiration.

If you're ready to propose, Chicago is a city that's brimming with possible settings for your special moment. The city has made it easy for you to scout out places to propose: It has a great variety of online tours of Chicago, with themes ranging from Parks to Music & Art. 

When you've picked out the perfect diamond cluster ring, consider popping the question in one of these romantic places.

Where to Propose in Chicago

1. In a beautiful outdoor setting

One of the most popular spots in the city is Buckingham Fountain in Grant Park. The fountain lit up at night is breathtaking. 

Lincoln Park has many lovely spots for those who are ready to propose. Lincoln Park Zoo is free of charge and open 365 days per year. It features a full calendar of special events, including tours of the beautiful gardens. Take a walk to the Alfred Caldwell Lilly Pool or pack a picnic to enjoy at sunset by Lincoln Park Lagoon and get down on one knee in the grass. Remember to bring champagne!

Millennium Park also offers a number of charming places to propose. Consider a leisurely stroll in Lurie Garden, or visit Cloud Gate, a giant public sculpture nicknamed "The Bean." It reflects the city skyline in its face of polished stainless steel. Stand under the archway of The Bean together when you pop the question. The reflection of the diamond cluster ring in the metal sculpture will dazzle her! 

2. Over a romantic dinner or drinks

North Pond is a favorite for many locals and visitors in Chicago. Nestled within Lincoln Park and set beside a pond, the restaurant has a romantic view of the city skyline. The menu at North Pond sources fresh ingredients from local farmers. Splurge on the seasonal tasting menu for your special occasion.

There are few meals more romantic than fondue, and Gejas Cafe doesn't disappoint. Choose from the extensive wine list and enjoy dinner with live flamenco music in the background.

Take her breath away with a view of the Chicago skyline at night from the Signature Lounge on the 96th floor of the John Hancock Center. You'll love the premium martinis and gourmet menu, which will complement her diamond cluster ring perfectly.

3. On a lighthearted adventure

If your lady loves cheesecake, take her to the famous Eli's Cheesecake for a tasting. If you call ahead and explain that you're ready to propose on-site, you may be able to convince the staff to prepare a couple of slices with "Will You Marry Me?" written on them in icing.  

A boat tour of lake Michigan is a beautiful excursion by day or night. There are so many companies and routes to choose from that you're sure to find a trip that she'll love.

Catch an evening comedy show at the renowned Second City, which has graduated performers including Stephen Colbert and Tina Fey. The actors are so accustomed to improvisation that they may enjoy incorporating your proposal into a skit. If you know that your lady will be thrilled by receiving a diamond cluster ring onstage before an audience, then this is the opportunity of a lifetime!

If you think you might be ready to propose, take a look at our selection of diamond trio rings and see which set speaks to you!

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About the author

Melia Dicker

Melia Dicker is a California native turned Southern belle. She lives in Jackson, Mississippi, and is a founding partner of Creative Distillery, the design and communications studio that she runs with her husband and sister. Melia specializes in narrative nonfiction and has written for a variety of blogs and mainstream publications. She married the love of her life in February 2011 and stayed within a modest budget by using many of the tips suggested on the My Trio Rings blog. Melia writes about food and relationships (the finer things in life) at www.eatdrinkandbemarried.com.

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