In a city filled with world class cuisine, romance and dining are all but inseparable, with restaurants perfect for each state of the seduction process. Here’s a rundown of Chicago’s most romantic dining spots for every occasion, from unforgettable first dates, to popping the question, to celebrating milestone anniversaries. Confirm your reservation, make sure there’s nothing stuck in your teeth, and let the sweet-talking begin.


Step 1: The First Date

The Violet Hour

It’s swanky and smooth with hard lines and soft light, old-fashioned cocktails and modern mixology. Meet up for drinks, and share well-crafted small plates and light-hearted conversation. Grab her hand by the fireplace; watch him smile under the light of the chandeliers. Make a toast to the perfect first date.

Step 2: Eat Together

David Burke’s Primehouse

Time to get cozy in a plush, red leather booth. To heck with conventions—sit on the same side. Ask for a tour of the dry-aging room to get some insider knowledge about the steak of your choice, then return to share your meal, elbow-to-elbow. You’ll be as entranced with each dish as you are with each other.

Step 3: Romance Is In the Courses


True love takes time. Test your patience and stoke your romance over a fine dining experience you’ll never forget. Watch and react together as a culinary performance unfolds in front of you. You’ll have plenty of time to discuss the surprises as you savor each bite before moving on to the next course.

Step 4: Make the Move

The Signature Room

Think your names are written together in the stars? Sit on top of the world, overlook the city with a champagne flute in hand, and pop the question. Hailed as one of Chicago’s best spots to get engaged, The Signature Room has launched a thousand happy marriages. With 360-degree views of the entire city, you’ll get the sense you two can conquer anything together.

Step 5: Legendary Love

The Pump Room

You’ve done it! With such a timeless love, the two of you will fit right in at the legendary Pump Room at the Public Chicago Hotel for your anniversary celebration. Dress up and drape your night on the town in the kind of elegance Bogart and Sinatra once enjoyed, along with sophisticated food and impeccable service.


There you have it—true love and romance in Chicago, as easy as 1 through 5.

Our writers' favorites

- Enter Your Location -
- or -