Valentine’s Day Proposal Ideas Chicago

February 7th, 2024

Valentine’s Day is well-known for being a popular day for proposals. If Valentine’s Day is the day you plan to pop the question and you are out of ideas for where or how to pull it off, we are here to help. Whether you’re a resident of the Chicago area, or just plan on visiting, here are a few Chicago Valentine’s Day Proposal ideas. 

Chicago Photo Shoot

Chicago is a beautiful city with so many places to take amazing photos. If you’re looking for an excuse to visit local landmarks to get that perfect engagement shot, a Valentine's Day photoshoot might be the perfect one. Ask a friend or hire a photographer to capture those Instagram-worthy photos. 

Navy Pier 

Navy Pier is an iconic Chicago location and makes for excellent photos. Take your time walking along the river, finding the ideal proposal spot, and ask the question when you find the ideal place for a photograph.

North Avenue Beach 

This beach has a view of the northern skyline with the lake all around you. Right before sunset makes an ideal time for photos at this location.

The Chicago Riverwalk

Take photos of your romantic stroll along the river, with no pressure to propose until you feel the moment is right.

Local Museum 

Are you both lovers of history, or maybe art? A museum proposal might be for you! 

The Art Institute of Chicago 

The Art Institute of Chicago is filled with timeless art housed in a beautiful building, ideal for art lovers. 

The Field Museum

If you love history, The Field Museum is filled with history and unique artifacts. Tickets are free on Wednesdays from 9:00 am-5:00 pm for Illinois residents. 

The Museum of Science and Industry 

The Museum of Science and Industry has many things to do and see that make this spot not only a good proposal destination but a fun date overall. 


Unique fancy restaurant

For any fancy restaurant, we recommend making reservations well in advance, especially on Valentine’s Day. To name a few, here are some unique fancy restaurants in Chicago.

BLVD Steakhouse is inspired by Hollywood’s Sunset Blvd, bringing to life Old Hollywood glamour and luxury. Sepia is a Michelin-star restaurant that has a vintage-contemporary feel, built from an 1890 print shop. This restaurant is unique in both its origin and its menu. Venteux is a French restaurant that exudes a romantic Parisian atmosphere. 

Gourmet meal at home

If you’re looking to keep things a bit more private, a candlelit dinner at home is always a romantic option. Get together some candles, roses, linens, and ingredients, and get to cooking! Of course not everyone has the ability or time to put together a gourmet dinner, so ordering fancy takeout is fine too.

Revisit the first restaurant date

If your first restaurant date was somewhere romantic that you’d like to revisit, this might be a good option. Bring back special memories and create a new one that you’ll never forget. 

Movie Date Night

Go to the movies

If there’s a movie out that you’d both be interested in seeing and you both love the movies, going to the movies could make for a romantic proposal spot. Whether you coordinate with the theater to help you pop the question when the movie is over, or you hide the ring in the popcorn, there are many possibilities for a theater proposal. Some theaters will even display a “Will You Marry Me” on their marquee if you communicate your plan with them to get down on one knee as you approach the theater. 

Get cozy at home

For this proposal idea, the goal is to create a cute, comfortable, romantic atmosphere “for Valentine’s Day”. This shouldn’t be just like any other at-home movie date night. Set up cozy blankets, turn down the lights, light some candles, gather the snacks, and sprinkle some rose petals. Make it feel romantic and be sure to agree on the movie ahead of time to avoid searching for an hour for something to watch. 

For these proposal ideas, most of all, do not forget the ring. James & Sons Fine Jewelers wishes you the best of luck and a Happy Valentine’s Day!