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"Not every romantic outing needs to be a “whole thing”—but when you are trying to make it a “whole thing,” check out Tre Dita in Lakeshore East. First off, this Italian restaurant from the chef behind hyped-up spots like LA’s Funke is in the St. Regis Hotel, so dining in a five-star hotel where a room costs $800 already makes a statement. But even if you don’t plan on booking a room, eating incredible housemade duck ragu pappardelle and drinking excellent Italian wine next to a gorgeous view of the river feels nothing short of luxurious. Reservations show up on OpenTable a week in advance at midnight, so you’ll need to stay up to book a dinner that’s later than 4pm but earlier than 9pm. The bar seating at Bar Tre Dita next door is also first come, first serve if you want to try an old-fashioned walk-in (the menu is more limited, but still has many Tre Dita favorite’s like pastas and their fluffy schiacciata)." - adrian kane, john ringor, veda kilaru, nick allen