Cuban Sandwich in Chicago?
Just one note to add with respect to La Unica: it can be a little hard to find if you don't have the exact address (and perhaps still a little hard even if you do). It is really a grocery store with a smallish cafeteria-like restaurant in the back corner. So when you think that you've incorrectly walked into a grocery store, don't fret -- you're in the right place.
El Prado on Lake Street just west of 1st Avenue in Maywood serves the very best Cuban Food around. It looks and feels like a prohibition era speakeasy. Although a bit dingy, this place has character. Lot's of oldtimer Cubans sipping cafe con leche here. I've been dining here as long as I can remember...maybe 35+ years. My parents used to hire Cuban Bands back in the day and throw huge parties in the basement and serve Cuban Food from El Prado. El Prado brings back fond memories.
Cafe 28 at 1800 W. Irving Park Road serves very good contemporary and traditional Cuban and Mexican food.
The employees from the now defunct Ambassador Cafe opened a new Cuban restaurant on Division (or is it Chicago Avenue?). Anyone know the name and address. Should be pretty authentic.
Having lived in NYC for 8 years - I share your pain (chow-longings.) We love Cubana sandwiches so much we've actually learned how to make them (good authentic ones!) - but it's a lot of work and time consuming. So here are some spots you might want to try (with a few notes/comments from us.)
There are a number of humble places on North Milwaukee Ave . (say 1200 to 2800 north) most are cash only:
Cafe Con Leche (2714 N. Milwaukee)
is kind of Cuban/Mexican - with pretty decent Cuban sandwiches and strong coffee.
Cafeteria Marianao (2246 N. Milwaukee)
Opens at 7am. Tasty Cubano sandwich is (was?) only $2.50! There can be long lines at peak hours.
Further north you might consider:
Sabor a Cuba (1833 W. Wilson Ave.)
The service here is utterly wretched so you might consider doing carry-out... but the Cuban sandwich ($4.95)is quite good. It's BYOB if you eat in - and expect rude AND slow service.
La Unica (1515 W. Devon)
Is probably our current favorite - even if some people complain that the bread is not authentic (actually it is authentically Cuban - just not traditionally used in this sandwich. Still it's very good and some people claim it's the best in the city. (Note: very rarely, but occasionally the kitchen does have an off day.)
Tropi Cuba (3000 W. Lyndale)
Makes very good pressed sandwiches, including the Cuban. It is actually a grocery store with a "cafeteria - style" eatery. AT the check out counter they have a variety of yummy fried appetizer type goodies for a buck.
If you are looking for a trendier spot with a lively atmosphere and over-priced but good drinks, check out:
Coobahs (3423 N. Southport)
Very popular, upbeat and LOUD music. Good Cuban sandwiches cost $8.50 the last time we were there.
Cafe La Guardia (2111 W. Armitage)
Is a lively spot and often very crowded. People seem to either love the place or hate it. Cubana and Jibarito sandwiches are both pretty good.
Hope this helps... I know "chow" beauty is often in the eye of the beholder. So welcome to Chicago and good luck!