The Best Chicago Date Night: Dinner at Adalina and Drinks at Rose Lounge
Looking for unforgettable date night ideas in Chicago this summer? Whether you’re planning a romantic evening for someone special or celebrating a milestone together, the Gold Coast offers no shortage of beautiful backdrops—but few match the sophistication and allure of pairing dinner at Adalina with cocktails at its hidden speakeasy, Rose Lounge.
From candlelit pasta dishes to velvet-draped lounges, this Gold Coast gem checks every box for the best date night in Chicago.
Start Your Night with Dinner at Adalina: A Top Romantic Restaurant in Chicago
Tucked into the heart of Chicago’s Gold Coast, Adalina is a modern Italian restaurant that blends timeless elegance with culinary innovation. Led by Michelin-starred and Top Chef alum Soo Ahn, the menu reimagines traditional Italian dishes with bold, contemporary twists—earning acclaim for some of the best pasta in Chicago.
Enjoy a thoughtfully curated wine list and start with shareable signature plates before diving into house-made stuffed or extruded pastas. With its dim lighting, plush interiors, and impeccable service, Adalina offers one of the most romantic restaurant experiences in Chicago.
Open-Air Romance: State Street Patio & Breezy Bar Seating
For warm summer nights, Adalina’s State Street patio and floor-to-ceiling retractable windows in the upstairs bar invite you to dine with a breeze. Whether seated outdoors beneath twinkling lights or sipping wine near the windows that open onto the city, the atmosphere is light, intimate, and distinctly Chicago.
End the Night at Rose Lounge: A Hidden Speakeasy in Chicago
Once dinner wraps, surprise your date by slipping behind a secret door and descending into Rose Lounge, Adalina’s plush underground speakeasy. With its velvet banquettes, glowing chandeliers, and a marble horseshoe bar, this space oozes mystery and charm—making it one of the best late-night cocktail lounges in Chicago.
Sip on expertly crafted cocktails made with premium spirits, and if you're there on select nights, enjoy the ambiance of a live DJ set. Whether you’re cozied up in a corner or dancing under the lights, Rose Lounge offers an unforgettable nightcap.
Why This is One of the Best Date Night Experiences in Chicago
From expertly plated pastas to after-dinner cocktails in a candlelit speakeasy, Adalina and Rose Lounge deliver an effortlessly romantic evening—all under one roof. Whether you're celebrating something special or just want to impress, this Gold Coast destination is designed to leave a lasting impression.