Here are some comments on previous comments as well as a few new ones, roughly organized from north to south. It’s not meant to be at all exhaustive, there’s a lot more to “discover.”
Many of the Pilsen favorites are within a block of Ashland on 18th Street.
Yes, a detour on 18th will be well rewarded. Likewise Cermak but you’ll have to go a bit farther (west) from Ashland.
Kiki D's (Home of Carnitas)
4117 South Ashland Ave
Kiki D’s big sign is gone but I think it’s still the same popular place. It looks like a fast food restaurant (which I suppose it is) but don’t let that stop you.
Mama Nena’s (1623 W 43rd) is a Chicago-style shrimp house with a Mexican twist. Not bad at all. Somewhere I have a write-up I’ll try to dig out.
Supermercado La Internacional (around 46th, west side) has an always-crowded taqueria in the back I’ve long wanted to try.
Las Palmas
(was Restaurante Oaxaca)
4612 S Ashland Av
Haven’t visited since Restaurante Oaxaca closed but this place now goes by the name Las Palmitas. Not sure if it has new owners.
A detour on 47th is very worthwhile. Between Ashland and Damen is the dense, vibrant Back of the Yards business district. Have a taco al pastor at Atotonilco, a bowl of carne en su jugo at Los Altos, a taco de ojo at El Arco, a taco de pescado (or al pastor) at Don Cuco, the parillada at La Cecina. Pick up some rye bread at Baltic Bakery (Hermitage). There’s a lot more to explore.
Tropic Island Jerk Chicken Restaurant
419 E 79th St (and Ashland)
Unfortunately, Tropic Island is no more at this location. (The original is still there further East at 79th & Jeffery). This location is now a place called Slabs, which seems to be a rib shack with a few tables.
As others mentioned, Tropic Island is at 419 E 79th (near King, not Ashland) as well as 1922 E 79th. The Slab BBQ is at 537 E 79th. I’m pretty sure all three are currently open. The reason for the confusion is probably because Tropic Island used to be at 537 E 79th. It moved a block west to 419 around 2000. The Slab opened at 537 E 79th a year or two ago.
JR's has moved to S. Indiana / 36th St or so...
JR’s Caribbean Hut was originally at 7960 S Ashland, on the NW corner of 80th. It closed several years ago and reopened across the street at 7959 S Ashland, on the NE corner, where it still is. Another JR’s opened on S Indiana. I think, but am not sure, all three are/were related.
GWiv suggested:
Harold's Chicken 3B
8316 S Ashland
I hope I’m not putting words in his mouth but I don’t think Gary particularly recommended this Harold’s. It wasn’t terrible but wasn’t one of the better ones either (the chicken art is excellent though). Harold’s is well represented on S Ashland so the chicken-loving commuter will have plenty to choose from. Other HCSs are near 56th, 63rd, 68th, and 92nd.
Paul Mollica noted:
Mississippi: Mrs. Johnson's Soul Food., Ashland and 83d
A good place. More to try: Vaughan’s (67th), Morning Glory (77th; I like the looks of this new one), Morrison’s (81st), Granny’s (85th).
If your detour takes you to southbound Vincennes take a left at 115th st cross over the expressway and pull into "I-57 Ribs" Southern style and cooked on a grill. These ribs are the real deal.
I-57 Barbecue is not bad but I’d suggest tips (and maybe links) instead of ribs. It looks like I-57 is getting ready to open a new place at 6514 S Western in the old Rib Inn location.
This new commute isn’t sounding so bad, is it?