It’s the most wonderful time of the year – time for holiday proposals! We’ve got the ring and the date idea picked out, and you make the reservations. Have an adventure around Chicago and stop by some winter wonderlands, fine dining, and James & Sons of course!

The Perfect Engagement Ring at James & Sons

 TACORI Engagement Rings

We know choosing a ring can be a big deal, and proposing is an even bigger milestone to celebrate. That’s why James & Sons is here to help you propose confidently this holiday season. Come browse hundreds of stunning engagement rings from top designers like TACORIFanaHearts On Fire, and more at our Chicago location. 


These engagement rings from TACORI are a favorite at James & Sons. From round brilliant to emerald cut center diamonds, platinum to yellow gold, diamond bands and solitaires, we’re sure you’ll find the perfect engagement ring to pop the question with.

Dinner Plans in Chicago


Coda di Volpe

Image credit to Coda di Volpe Management | Coda di Volpe


For your first stop of the evening, head to Coda di Volpe. This Southern Italian restaurant has fine dining options, and you’ll be sat in a cozy, romantic atmosphere. The restaurant’s dishes include pasta, pizza, fish, steak, and more. Kick off the festivities with a nice glass of wine or a handcrafted cocktail, enjoy your dinner, and finish with a decadent dessert! 

Holiday Activities in Chicago

 Gallagher Way Winterland


Image credit to Gallagher Way (Facebook) | Gallagher Way


After dinner, make your way over to Wrigley Field for Winterland at Gallagher Way and the Christkindlmarket. The baseball stadium and surrounding areas have turned into a winter wonderland filled with pop-up shops, food vendors, and activities. You can grab a hot chocolate in a Christkindl Market souvenir mug, walk through the shops, see the lights, or even go ice skating all in this one-stop Winterland! 

Wrapping Up the Evening

 Mordecai Wrigleyville


Image credit to Terrence Antonio James (Chicago Tribune) | Chicago Tribune


Whether you pop the question at dinner or wait until you’re under the Christmas lights, you can celebrate the occasion together at Mordecai, a high-style cocktail bar and lounge. The intimate atmosphere is just across the street from Wrigley Field, making this a great spot to wind down from an exciting evening. 

Propose Confidently with James & Sons

We know proposing is a huge milestone, and we know it can be nerve-racking as well. That’s why James & Sons is here to help you propose confidently. Engagement rings from top designers like TACORIGabriel & Co.Noam Carver, and more are waiting for you at one of our four locations in ChicagoNapervilleOrland Park, and Schererville