I think this has been covered before, but I can't find it. Southport has its ups and downs, but it does have sidewalk dining in spades.
I live in precisely the area you describe. Argentine steakhouse Tango Sur and the owners' parents' adjoining South American bodega and meat market, Mercado are at Grace and Southport, across from the picturesque Blaine grammar school.
Cullen's is the Irish bar a few doors south and across from it is the New Orleans place Blue Bayou. Both at one time had very good kitchens. Both had fallen so far by the end of last year that I have more or less written them off except for the odd beer and burger on a nice day.
Banana Leaf is serviceable Thai, as is the idiotically named Once Upon a Thai, both on Southport north of Addison. But I don't go to either since TAC, Spoon, Sticky and others are so near.
Neybours is better than your average Wrigleyville bar, owing to the chef-owner's active role. Good bar food including a courageous lemongrass and fish sauce flavored rack of ribs and mini burgers.
D'Augustino's is the old timer on Southport. Do not get anything other than the super thin crust pie with sausage. It's a solid version of the Chicago tavern pizza that is discussed in Time Out this week.
People seem to like the Southport Grocery, with its fancy prepared foods and light dishes. Every single popular Northside neighborhood has one of these fancy grocery cafes; I have been in most if not all, and I have yet to have my lightbulb go off in any of them.
The bar food at Justins, Southport Lanes, and Schoolyard is all fair to good, as bar food goes. NB the fairly decent fish tacos at Schoolyard, which also appear at the very pleasant but Trixified Brownstone (same owners) nearby on Lincoln, north of Grace.
Coobah is the Latino-Filipino fusion bar-restaurant that passes for sophisticated dining on Southport, and it's not half bad. I have never been able to bring myself into the teeny-bopperish SoPo (Southport, get it?) on the other side of the street. Mystic Celt is the huge Irish Pub that used to be the French Bistrot Zinc. Eh. Then there's a Potbelly, an Einstein Bagel and an Ann Sather Cafe if you desire chain grub. Closer to Belmont you have one of those dumb mongolian bbq places.
It's turning into an ice cream street, for better or worse (mostly the latter). You have the South Beach-Eurotrashy Australian Homemade (actually from Belgium and pretty good but absurdly expensive and filled with air), you have the bare-bones place that sells Double Rainbow, you have a Cold Stone, which is taking over the universe with its gimmicky mall food, and soon, a huge retro DQ in the old Banana Leaf space next to Mercado. The DQ owners have quite the sense of humor. Before the sign was installed, they put up huge posters declaring that a Hooters was coming. What does it say that I'm looking forward to the DQ? Three words: peanut buster parfait.
Noteworthy and nearby (look for posts): Biasetti's (cheap steaks fine au gratin potatoes and creamed spinach, dine with CPD detectives and bookies); Resis, best German food and beer garden around; Diner/Dinner Grill; Byrons (hot dogs near TAC); El Llano and the Flying Chicken (Colombian places on Lincoln between Addison and Irving); Cafe 28 (fancier Cuban/Mexican place apparently named after Cafe Tacuba's address). Then you have the rich bounty of mostly mediocre but sometimes better that is Clark Street near Wrigley, Lincoln Square, Andersonville, and Uptown/Argyle all within short cab or L rides. The world is your oyster.