Let me start by offering up Cafe Marianao.
Marianao is named after a beach town near Havana. Our Marianao is a quintesentially Cuban establishmnet, though I'd wager that the majority of customers are actually Puerto Rican, Central and South American. Marianao is hyper-urban but not particularly Chicagoan (even Latino-Chicagoan) in a way that is hard to pin down. The whole experience, from the physical plant to the customers to the staff seem to have been lifted from a corner in the DR, or Panama, or Calle Ocho and dropped onto Milwaukee Avenue. Marianao is Pan-Caribbean Afro-Latino, I guess. I think that's a census category.
The coffee, both the cafe Cubano and the cafe con leche, is right. It fits squarely within the paradigm. It is as it should be. If you don't like it, well, don't blame Marianao and don't expect to like the coffee in Miami or Tampa or Havana. It is not espresso in the Italian tradition, it is cafe Cubano in the Cuban tradition, as much about sugar and technique as it is about coffee beans. The importance of the coffee at Marianao is reflected by the fact that Marianao offers, exclusively, Cuban toast -- pan tostado con mantequilla. Only at Marianao can one have the traditional toast, pressed on the plancha, dipped into cafe con leche. It is the best breakfast in Chicago.
The sandwiches are very good too, particularly the sandwiches that are not the sanguiche mixto, the "Cubano" as they say. I'm something of a purist and think that a really good Cuban sandwich place should not use processed cheese and should roast its own pork daily. For Cubans here, I prefer La Unica. But the Cuban steak sandwich and the "pan con tortilla" or omlette sandwich are very good examples of each. And the vibe, though sometimes intimidating, is great.
Marianao remains somewhat mysterious. While often packed, few long-time, Chicago-area Cubans know about it in my experience. The clientelle are more recent immigrants, largely single men who, like recently arrived Greeks, Barese and Balkans, have a cafe culture void that must be filled -- in this case, by Marianao.
Chicago is thin on Cuban, but it does have two establishments that I sincerely believe would make it in Miami, La Unica and my GNR nominee Marianao.
Cafe Marianao
2246 N. Milwaukee Ave.
Chicago, IL 60647
773-278-4533
La Unica
1515 W. Devon Ave.
Chicago, IL
773-274-7788