We also highly recommend indulging in the Bertha Brownie-the dessert was literally invented here in the 19 th century, and the kitchen still uses the very same recipe.ģ1, 17 E. The food is every bit as savory as it is at the sit-down restaurant (you can happily nosh on everything from a burger to pork ribs) and come holiday time, you won’t see a better indoor tree display. While the restaurant is perfectly lovely, it’s the Lockwood Bar, which offers a bird’s-eye view of those stunning ceiling murals from Art Deco painter Louis Pierre Regal and 24-karat gold candelabras by Tiffany & Co., that will really take your outing’s romance factor up a notch.
Even more romantic? Sharing a meal and a cocktail at the eatery that overlooks it. The Palmer House Hotel may be more than 150 years old, having originally gone up just 13 days before the Great Chicago Fire, but its French-inspired lobby remains one of the most romantic spots in the city to this day.
Specialties: Pork ribs, Lockwood burger, Bertha brownie. Beyond the rotating grub, couples can also head over to the tasting room for a pre- or post-dinner Napa-style wine experience or take a tour of the restaurant’s pièce de résistance: a 50-foot tall glass wine enclosure with a spiral staircase that holds roughly 1,600 bottles of wine from around the world: truly a sight to behold.ģ1, 58 E. There’s also the Esquire menu, however, for those who tend to latch onto tried-and-true favorites, like the classic tuna tartare, braised shortrib or crispy Yukon potatoes (*raises hand*). Thanks to the restaurant’s Visiting Chef Series, which brings culinary masters from around the world to its kitchen for extended runs (currently, Top Chef star Brooke Williamson is up to bat), the chances of getting bored with the menu are slim, even if you’ve dined here before. If it’s a culinary experience you and your hunny are after, the recently re-opened Esquire by Cooper’s Hawk will be a home run. You also just might spot a star or two-the cast of Vanderpump Rules was filming during my last visit.ģ1, 912 N. Once you’ve finished your meal, you can turn up the heat even further with a visit to the restaurant’s basement sultry Rose Lounge, where you can sip on cocktail specialties like The Centerfold-400 Conejos mezcal, aperol, Genepy del Alpes, citrus, pineapple and a smidge of haberno-to your heart’s content at the ultra-exclusive, secluded corner tables. Set in the city’s Gold Coast, the interior more than lives up to the neighborhood’s ritzy reputation with its stunning chandelier (this TikTok video of it is basically ASMR fodder), and the menu Italian menu is straight-up droolworthy (we’ll take our fill of chestnut-stuffed cannelloni or salmon vesuvio any night of the week). When you really want to wow your date, head to Adalina: A single glance at the dining room is enough to induce a swoon. Specialties: Charred octopus, veal chop parmigiana, campanelle. (Trust me, after trying just about everything on the menu, I can confidently say you’ll be hard-pressed to have a bad meal here.) The drinks are nothing to sniff at should you need an icebreaker (think Limoncello martinis), and while it does get busy at times, there are very few spots in the restaurant where you’ll feel like another table is sitting on top of you-something that can’t be said for most.ħ7, 5343 N. The rustic Italian fare is also consistently delicious. 
With its warm and inviting candlelit glow, it's plenty cozy, and the sturdy wooden booths are big enough for two to sidle up in side-by-side.
As one of the first places my boyfriend took me to, this place left such an impression that it became our official "spot": We've been celebrating special occasions here for more than 13 years now (with plenty of Valentine's Days included). When it comes to romantic restaurants in Chicago, there's none more underrated than Calo Ristorante.
Specialties: Baked clams, fried calamari, gnocchi gorgonzola.
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