Best Places In Chicago To Propose

August 31, 2013 7:00 AM

(Photo by Jeff Schear/Getty Images)

Asking someone to spend the rest of their life with you is an important and personal event. When and where you pop the question is equally personal and each person will have a different idea of what the perfect romantic setting for their proposal is. Here are a few that you may not have considered with various tastes in mind.

(Photo by Jeff Schear/Getty Images)

(Photo by Jeff Schear/Getty Images)

The Art Institute of Chicago’s South Sculpture Garden
111 S. Michigan Ave.
Chicago, IL 60603
(312) 443-3600

When thinking of romance, the Art Institute doesn’t generally pop first into one’s mind, however, an out-of-the-way and sometimes overlooked part of the property is the Sculpture Garden on the south side. The south garden is on the Grant Park side of the Institute. In addition to a picturesque fountain, the trees that have been planted here give the area an almost magical feeling. This is a perfect, unique setting for a marriage proposal with the added bonus that it’s almost certain to be unexpected should you want the question to come as a surprise.

Promontory Point
5491 S. South Shore Drive
Chicago, IL 60615
(312) 747-6620

Located in the Chicago Park District’s Burnham Park, Promontory Point is a beautifully designed nature area on the lake. The sounds of the city seem to melt away inside the park and, apart from other people walking through to take in the atmosphere, the area is quiet and peaceful. The view of the skyline is argued to be the best in the city from both the north and south side. This is ideal for a picnic or just to sit on the rocks and take in the view and it is accessible by biking up the Lakeshore Trail or driving to the park. It is a perfect romantic spot to pop the question in a peaceful and natural setting without leaving the city limits.

(Credit: / Matt Haas)

(Credit: / Matt Haas)

The Crystal Gardens
Navy Pier
700 E. Grand Ave.
Chicago, IL 60611
(312) 595-5436

One may initially think that any spot on Navy Pier is the least likely to be secluded, peaceful and romantic, but the Crystal Gardens is the exception. Enclosed in a structure seemingly made out of windows, there are spectacular views of Lake Michigan and the skyline. The gardens are littered with fountains with gardens of tropical plants and trees throughout. Although events and weddings are often held in the Crystal Gardens (another sign that you’ve found a romantic spot), if there are no events going on, anyone can walk through and sit in the gardens for as long as they like.

Related:  Most Romantic Spots In Chicago

Osteria Via Stato
620 N. State St.
Chicago, IL 60610
(312) 642-8450

If you’re the type that would prefer a more traditional proposal over a romantic dinner, Osteria Via Stato may be the restaurant for you. The Italian restaurant uses local ingredients, the food consistently gets great reviews and the wine list is extensive. The atmosphere is romantic and inviting. Be sure to make reservations ahead of time to ensure a table on the night of your proposal. The restaurant is large and does include a patio area for outside dining in nice weather. Although it is spacious, Osteria Via Stato is divided up into several rooms so there is still a feeling of intimacy no matter where you are seated.

1820 Tower Drive
Glenview, IL 60026
(847) 729-9463

If you want to get out of the city for your proposal (but not too far out), a wine bar in Glenview may just be the perfect place. Flight is just out of the way enough to be a hidden gem, but frequented enough to be able to scan some reviews beforehand. The wine list is extensive, as expected, but there is also a good beer list and it serves its own fun cocktails. You can always sample a flight (hence the name) before deciding on the beverage you choose for the evening. The food is also good, but the ambiance (most important for a romantic endeavor) is warm and inviting. The bar area is casual, but the separate dining room is perfect for date night. It’s rarely crowded which is perfect for an intimate proposal.

Related: Most Romantic Wedding Proposals

Meredith Lyons is an actor, competitive fighter and fitness instructor in Chicago who also owns an amazing cat named Jake. Meredith has been writing on Examiner as the Chicago Martial Arts Examiner since 2008. Her work can be found at

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