Kick off the evening with a locally brewed IPA while the house pianist tickles the ivories.
Within restaurant Dusek's next door, amble down into Punch House for one of its fruity, flowery bowl drinks. This is also one of the few places in town where you can have fondue for dinner while resident DJs warm up the beats. Then you'll head to neighboring music venue Thalia Hall, where indie heroes like M Ward and Rodriguez rock the house on the regular.
Sleep in before a late brunch at Hash; we recommend the Pork Bubble & Squeak (pork shoulder, sweet potatoes and Brussels sprouts in a mustard cream sauce) with bacon-fat hash. This is a meal that may need a bit of "walking off," but Wicker Park and Bucktown's preponderance of vintage vinyl makes it the perfect place for music lovers to get a bit of exercise.
Amid the funky boutiques and independent art galleries, you'll find a full menu of "licorice pizza." Reckless Records is known for a consistent mainstream selection at reasonable prices. Dusty Groove is known for obscure imports and basement treasures, with a deep inventory of jazz, hip hop, Afrobeat and Latin. Not sure what you're looking for? Hit up a friendly Shuga Records staffer for a tour of the stacks.
Tonight you're off to Lincoln Park, where the blues are just a little bit bluer. Start with a Dutch-Indonesian gourmet dinner at de Quay, a flavorful culture clash. Then take your pick of authentic blues bars and juke joints that are mainstays of the city's music landscape.
Visit Kingston Mines for blues on two stages, The Wild Hare & Singing Armadillo Frog Sanctuary for Caribbean beats, or B.L.U.E.S. for straight-ahead bluesmen with serious guitar chops. Continue your grand tour at modern, mid-sized venue Lincoln Hall.