Like a Negroni with a cocktail umbrella, Ummo in River North is both serious and playful. On any given night this Italian restaurant is full of blazer-clad business types sipping espresso, and twenty-somethings in Gucci polo shirts pregaming with pasta. It’s a loud, busy, and fresh alternative to old-school red sauce spots that have been using the same white (perhaps now off-white) tablecloths for decades. Glasses clink, funk music blasts, and conversations about Montessori tuition and CDMX work-from-home trips are overheard. Servers zip from table to table. The menu is a mostly successful mix of classic and creative Italian dishes. Pastas are generally good—like cacio e pepe, or lobster ravioli swimming in creamy butter ragu. Steak drizzled with herbaceous bagnetto verde and roasted chicken with polenta are cooked to juicy perfection. And the pomodoro e basilico is a stunning dessert cosplaying as a tomato. The “pomodoro” is filled with yogurt mousse, tomato and raspberry compote, and comes with a scoop of basil sorbet. It’s sweet, it’s savory, it’s delicious, it’s not a tomato. Ummo is fun—but has some issues. Tortellini al pesto comes out undercooked. The impressive wagyu tartare (served on a giant bone that looks like it’s on loan from the Field Museum) is bland. Plus, when it’s busy, you’ll wish your order came with a tracking number. None of this totally ruins dinner, but the eye-catching dessert loses its luster when it’s 20 minutes late. Despite its flaws, Ummo is still a safe bet if your friends put you in charge of a big night out. Especially after 10pm on the weekends. That’s when the late-night DJ set starts on the second floor, which goes until 2:30am on Saturdays. So if you're going bar-hopping after dinner and don't feel like playing “Where's The Shortest Line?” you can just stay here.