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If you’re not into wine, Maude’s Liquor Bar serves great cocktails in an intimate setting.Guide to Dating in Chicago: Get Artsy Learning is sexy.Or pledge your allegiance to Pizzeria Uno, the inventors of the deep dish. Impress your date by reserving spots at one of Chicago’s two 3-star restaurants, Alinea or L2O.Other date-worthy spots: Dine on Italian tapas at Quartino Ristorante and Wine Bar, share farm-to-table plates on Prasino’s great patio, or keep it casual with sandwiches at the cozy and charming Bourgeois Pig Cafe.Visit the conservatory and lagoon at Garfield Park, enjoy a two-hour Cinderella-approved Chicago Horse & Carriage ride through Grant Park, or spend the day in Chicago’s 1,200-acre Lincoln Park. Or grab dessert at Anthony’s Homemade Italian Ice as you stroll through Chicago’s Lakeview neighborhood.The Lincoln Park Zoo will bring out the wide-eyed kids in every love-struck couple. Dine on unique local eats and explore the city — on bike!
Al Capone and Charlie Chaplin used to hang out at this character-filled ex-speakeasy — not together, mind you.Make your date guffaw and check out world-famous The Second City or i O Chicago Theater.Smaller comedy clubs and amateur improv troupes will make sure every night is a hilarious one.Add a little romance and athleticism to a wintery date by lacing up your ice skates on the ice outside Wrigley Field.If you like heights, “skate in the sky” at the John Hancock Observatory, where you’ll overlook the city on the world’s highest rink.