937 N Damen Ave (773-489-0302)
Tenants in this space have changed over the years, but the life-size horse statue and eerie saddle sculptures (created by the building’s owner) have made this one of the more eccentric courtyards in the city. Now it has irreverent food to match, from precious brunch amuse-bouches to inventive breakfast (cured-trout quiche), lunch (braised-lamb crêpes) and dinner (a rotating four-course menu for $25) via chef Jeff Mauro. Bonus: While the former Sweet Cakes space in the back of the courtyard is empty, Jam has additional outdoor space.
FOOD9Quirky and exciting—morning, noon and night
DRINKS8It’s BYOB, and Lush is just a few blocks away.
CROWD7Expect a weekend wait.
VIEW8High walls block pretty much everything.
SPACE9Trees provide much-needed shade.