Best Places to Propose in Chicago
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 engagement ring, consider popping the question in one of these romantic places.
Where to Propose in Chicago
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.
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!
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.
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 engagement ring in the metal sculpture will dazzle her!
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.
Find a quiet spot by North Pond where you can admire the city skyline, the way Wes did when he proposed to his girlfriend Holly. The two met in a class their senior year of college; Holly fell for Wes’ smile, and Wes loved how Holly could light up a room. He had been running by the same spot in Lincoln Park for the past three years, and he knew he wanted to share this beautiful view with Holly for the rest of his life. He got down on one knee and proposed, and she said yes!
Proposal pictures and story sponsored by Paparazzi Proposals
When booking, enter code mytriorings$100 to receive $25 off the standard proposal photography package and $75 off a photo voucher for prints.