Subway: Blue, Red to Washington(312) 368-1900 atwoodcafe.com41.883188 -87.627855 1 W Washington St (at State St) Loop, Chicago
Breakfast (Mon–Fri), brunch (Sat, Sun), lunch (Mon–Fri), dinnerAverage main course: $25
This downtown standby draws mobs of tourists and local ladies seeking nourishment after a particularly grueling shopping session at Macy’s. For them, these updated American classics are perfect—sophisticated and unintimidating. Case in point: a winter menu that offers thyme-and-mace–roasted duck breast with mashed sweet potatoes and a dried fig gastrique; oven-roasted acorn squash over date-and-pistachio–studded couscous; and a warm apple-walnut dumpling served with vanilla bean ice cream.