![]() 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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