Chicago Engagement Rings

Chicago city featuring the famous bean.

Chicago proposal spots

There’s no shortage of stunning proposal spots in Chicago. Whether you’re looking for a venue with a view or a more secluded aesthetic, Chicago can make it happen. Want to pop the question with a scenic backdrop? Why not take a chance at the North Avenue Beach, Garden of the Phoenix, Alfred Caldwell Lily Pool, or the Lincoln Park Conservatory. Looking for something more urban? Go big or go home with a perfect skyline view. Olive or Millennium Park can give you a breathless view of the city as your proposal backdrop. If you’re aiming a little higher, you can always try the cupola at London House, or Cerise Lounge at Virgin Hotel Chicago to get a close-up view of the city’s architecture.

A white gold diamond engagement ring.


A round-shaped loose diamond.

The James Allen Guarantee

A warranty paper.


Our products are guaranteed to be free of manufacturing defects upon delivery and will be repaired and maintained for a lifetime by us.

A shipping icon.


We provide fast, free shipping, and insurance to various destinations worldwide. All items are securely packaged and insured during transit.

Hand holding cash.

Hassle-Free Returns

If you are not 100% satisfied with your purchase, you may return it in its original, unworn condition within 30 days, for a full refund or exchange.

A sparkling diamond.

24/7 Customer Service

Our highly reviewed team of non-commissioned diamond and jewelry experts is here to help you.


We are 100% committed to providing you with ethically sourced, high quality diamonds.

Chicago engagement ring FAQs

Is there a James Allen showroom in Chicago?

You can find the engagement ring of your dreams on and get free shipping to anywhere nationwide. Additionally, we have two beautiful locations in the USA, the first being our New York City showroom (don't forget to schedule an appointment in advance) and our official store in Georgetown, Washington, D.C

How can I choose an engagement ring if I'm shopping online?

We understand that buying an engagement ring online comes with many questions. At James Allen, we offer 100% free advice and will assist you in understanding the best diamond quality for your budget and unique preferences. Our non-commissioned diamond and jewelry experts are available 24/7. Contact us here.

Do I qualify for free shipping to Chicago if I buy an engagement ring?

Yes, when you purchase any item from we provide fast, free shipping and insurance to all our shipping destinations. USA orders that are greater than $500 in value are shipped via FedEx Priority Overnight. USA orders under $500 in value are shipped via FedEx Two Day Saver.