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:
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.
Dine Above the Loop at Celeste - Four stories of moody glam, including a rooftop garden oasis perfect for cocktails and city vibes.
Taste Elevated Comfort at The Duck Inn - Bridgeport’s beloved gastro-tavern serves signature duck dishes and creative twists in a cozy setting.
Experience Moody Minimalism and Big Flavor at Ada Street - Tucked away and dimly lit, this spot blends Mediterranean-inspired plates with indie rock attitude.
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.
Unwind Above It All at L H Rooftop - Views of the river and Lake Michigan pair with upscale American fare and vibrant cocktails.
Find Peace on the Plate at Eden Chicago - Fresh, seasonal ingredients—including herbs from their on-site greenhouse—shine in this West Loop sanctuary.
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.
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.
In Summary...
(and if you want to revisit my photo journey)- • Soak in Skyline Views with Style at Raised
- • Dine Above the Loop at Celeste
- • Taste Elevated Comfort at The Duck Inn
- • Experience Moody Minimalism and Big Flavor at Ada Street
- • If You Crave Bold Flavor and Cultural Depth, Feast at Demera Ethiopian Restaurant
- • Unwind Above It All at L H Rooftop
- • Find Peace on the Plate at Eden Chicago
- • Step Into Classic Italian Elegance at Formento’s
- • If Gluten-Free Goodness Is What You’re After, Start Your Day at Wheat’s End Cafe