If you’re planning a romantic night out in Chicago, I’ve got some spots you absolutely need to try. I’ve been writing about travel and food for 26 years, and every time I come back to this city, I find somewhere new that makes me want to linger a little longer. Whether you’re looking for candlelit corners, skyline views, or cocktails that feel like a love letter, I’ve found places that hit just the right note. You’ll love how the city mixes old-school charm with modern flair—I know I do. I always tell friends: if you want a date night that actually feels special, Chicago knows how to set the scene. So grab someone you love (or at least like a whole lot), and let me help you plan a night to remember.

Unique Romantic Restaurants in Chicago:

This riverside rooftop delivers bold cocktails, shareable plates, and some of the city’s best sunset backdrops.

Raised

Soak in Skyline Views with Style at Raised

- This riverside rooftop delivers bold cocktails, shareable plates, and some of the city’s best sunset backdrops.

Four stories of moody glam, including a rooftop garden oasis perfect for cocktails and city vibes.

Celeste

Dine Above the Loop at Celeste

- Four stories of moody glam, including a rooftop garden oasis perfect for cocktails and city vibes.

Bridgeport’s beloved gastro-tavern serves signature duck dishes and creative twists in a cozy setting.

The Duck Inn

Taste Elevated Comfort at The Duck Inn

- Bridgeport’s beloved gastro-tavern serves signature duck dishes and creative twists in a cozy setting.

Tucked away and dimly lit, this spot blends Mediterranean-inspired plates with indie rock attitude.

Ada Street

Experience Moody Minimalism and Big Flavor at Ada Street

- Tucked away and dimly lit, this spot blends Mediterranean-inspired plates with indie rock attitude.

Spiced stews, injera bread, and communal dining make this Uptown gem a soul-satisfying favorite.

Demera Ethiopian Restaurant

If You Crave Bold Flavor and Cultural Depth, Feast at Demera Ethiopian Restaurant

- Spiced stews, injera bread, and communal dining make this Uptown gem a soul-satisfying favorite.

Views of the river and Lake Michigan pair with upscale American fare and vibrant cocktails.

L H Rooftop

Unwind Above It All at L H Rooftop

- Views of the river and Lake Michigan pair with upscale American fare and vibrant cocktails.

Fresh, seasonal ingredients—including herbs from their on-site greenhouse—shine in this West Loop sanctuary.

Eden Chicago

Find Peace on the Plate at Eden Chicago

- Fresh, seasonal ingredients—including herbs from their on-site greenhouse—shine in this West Loop sanctuary.

Old-school charm meets modern finesse with handmade pastas and a stellar wine list in the West Loop.

Formento's

Step Into Classic Italian Elegance at Formento’s

- Old-school charm meets modern finesse with handmade pastas and a stellar wine list in the West Loop.

Dedicated gluten-free and delightfully indulgent—think waffles, pastries, and avocado toast worth the buzz.

Wheat’s End Cafe

If Gluten-Free Goodness Is What You’re After, Start Your Day at Wheat’s End Cafe

- Dedicated gluten-free and delightfully indulgent—think waffles, pastries, and avocado toast worth the buzz.

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