Proposing in Chicago around the holidays: Everything you need to know to plan the perfect winter engagement

It’s the most wonderful time of the year! No wonder the holiday season is the most popular time of year to get engaged! Twinkling lights, sparkly snow and the spirit of the holidays truly makes it the most romantic season. If you’re planning on proposing between the months of November through January, there are a few things to consider to ensure the most romantic, special proposal. As a wedding photographer in Chicago, I’m going to share some of my tips for proposing in Chicago around the holiday season, but many of these tips apply to any location this time of year!

The best places to propose in Chicago during the holidays:

Millennium Park Tree

Located right downtown near Michigan Avenue and Washington Street in Millennium Park, this colorful tree with a giant sparkling star is a beautiful backdrop for a proposal. Be sure to work with your photographer on lighting (see more about lighting below) and keep in mind it is likely going to be crowded.

Ice skating rink at Millennium Park

Ice skating with your bae around the holidays is so romantic as it is, and you’ll have a beautiful view of the city as the backdrop.

*Keep in mind that you/your photographer will need to receive a permit in advance for photos at Millennium Park!

Wrigley Building Tree

While the Millennium Park tree is always very colorful, the tree at the Wrigley Building in downtown Chicago is a bit more classy with white lights and a big red ribbon. The Wrigley Building is absolutely stunning and makes for a perfect engagement backdrop.

Chicago Theatre

The Chicago Theatre is another great place to propose, especially if you and your bae are into broadway. The sign out front is a classic photo opp in the city! 

Chicago Riverwalk

The Riverwalk has many great spots to get down on one knee at, depending on if you want the focus of the scenery to be the river itself, the bridges or buildings next to the river. There are so many great restaurants along the river that you could pop the question at too, like RPM Seafood and City Winery. 

Photography tips for a winter proposal:

Proposing before the sun sets

This time of year, it’s really crucial to consider the timing of your proposal to make sure the lighting works out right. Since the sun sets so early in the winter, I recommend planning your proposal anytime between sunrise to 3pm CST if you want to catch the expression and reactions the clearest. 

A romantic night time proposal

If you want the Christmas lights to illuminate the image for that romantic film feel, anytime after 4pm CST will be good! This lighting is not the most optimal for catching your partner’s reaction since things happen so fast, and with no natural light, the camera will be struggling to brighten up the image. It’s all up to your personal preference and what your vision is, and it can be totally worth it to get those romantic photos of your dreams. Just make sure you have a solid game plan with your photographer beforehand. 

Pause so your photographer can get the best shots

When you finally pop the question, make sure you stay down on one knee for a decent amount of time to make sure your photographer can capture the scene and all the emotions! Prepare a little speech or just speak from the heart to extend the time so your photographer can get environmental shots and reaction images to fully tell your proposal story!

How to announce your engagement during the holidays:

If you’re proposing during the holiday season, there’s a great opportunity to share the news in person if you get together with family and friends for the holidays.

A Thanksgiving announcement

If you’re sharing the big news at Thanksgiving, maybe you and your new fiancé could do the hosting so you could have both of your families there together. Have all your guests write what they’re thankful for on a cut out leaf, and as everyone shares theirs during dinner, you and your partner share that your leaf says something about being thankful for each other and looking forward to getting married. 

A family photo surprise

Another idea that works great if you’re together with family is to take a family photo, and make sure you and your fiancé are in the back. Use a self timer or tripod, and as the photo takes, you and your fiancé bust out a sign that says “We’re engaged!”

Holiday cards

Or, just keep it simple and send out a holiday card to all your family and friends with a photo that clearly shows your ring and says something like “The happiest season of all — we’re engaged!”



  1. […] One of the first things you’ll probably want to do after getting engaged is to tell your friends and family. You can do this by hosting a dinner party, posting on Facebook or Instagram, or calling people individually. If your proposal happens around the holidays, you’ll probably already have a few opportunities to be around your friends and family. Here are a few ideas of how to announce your engagement to friends or family at holiday gatherings.  […]

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