This is actually a redirect from the Mexico international board for someone that wondered about Mexican food in Chicago (an out-of-towner from Toronto). Sorry if some of it is a repeat.
I have been living in Chicago for the past 9 months, in Pilsen the historically Mexican neighborhood (my perspectives are pretty authentic, if I do say so myself, since I lived in Mexico, grew up in San Antonio (not really real Mexican food, but know how to compare to tex-mex), work at a Mexican organization and continue to leisurely study central Mexican cooking). So, I can suggest some off-the-beaten track places in Chicago, and perhaps suggest a typical place or two.
The typically suggested places (some of which I've eaten at, some not- I'll specify in parenthesis if I have) are:
Topolopamgo and the Frontera Grill are both Rick Bayless' restaurants (he's a PBS broadcasted chef, and is usually right on the money with his cultural food insight). I have heard mixed reviews on his restaurants, but his shows are wonderful and the way he prepares the food is quite authentic, particularly for the Yucateca cuisine. (have not experienced, but someday)
White people (as in folks that don't live in Pilsen, the neighborhood I previously mentioned where I live) tend to flock to Nuevo Leon (a few blocks from the 18th St Pink Line station). I think it is ok. The mural outside of the bldg is worth seeing, but I don't recall the food blowing me away with authenticity. It seemed more Tex-Mex, which is ok, since Nuevo Leon is a Texas border state. Now, I'll go to a place even if it is touristy so my lack of enthusiasm has little to do with that. (have been)
Another regular mention would be Cafe Mundial . The menu changes. I went on a day where I had amazing food (altho I'd be hard pressed to tell you what I had- so sorry- but I think it had something to do with goat cheese and possibly seafood). Out of the typical places this is the place I'd go again and again. I also work in Pilsen, so often walking to work I pass the place and look at the menu. It often looks appealing and creative, but not always. This may be borderline crazy, but their french fries with green sauce were amazing and I would definitely order that. (have been)
A few off the beaten path places:
I believe it is call Mexico Grill or Mexico Cafe. It is on the northwest corner of Damen and 18th St. I just went there the other day and was quite impressed with their enchiladas potosinos (the style from San Luis Potosi, where the friendly owner is from). I highly recommend them! They sort of remind me of a cross between an enchilada, a Mexico City style quesadilla (fried in a tub of oil) and an empanada. I'm a big fan of texture and these had a good combo of crunchy and soft. Also, their salsas were WONDERFUL AND they make hand-made tortillas which are the best.
Another one I'd try for the pozole (service is not the best and you have to specifically say you want all the sides) is El Alamo at Hoyne and 18th. Pozole is only served on the weekends. This place is a major whole in the wall- keep in mind. But the pozole is quite good.
For decent seafood I would try La Condesa on Ashland just south of Cermak. I was silly and ordered mole poblano (hey, I was “homesick” for Puebla after having just gotten back), so I can’t speak for the seafood dishes, but the mole was excellent! I think this place may have the best handmade tortillas in Pilsen.
La Fogata. This is where the politicos and the folks from the Mexican consulate come to schmooze. I think it is decent (again handmade tortillas). My partner (who is Mexican, so perhaps he has a bit more credibility than me) thinks it is fairly authentic. I think it is so-so authentic. It is supposedly an Italian-Mexican fusion, but really that translates to a typical Mexican-in-the-U.S. menu with some pasta dishes. My co-worker supposedly has his own plate on the menu that they named after him. Whatever.
Finally, dessert (and it is WORTH leaving the place you’re at to come to this place). I agree with Rick Bayless- he says the best tres leches cake is at Kristoffer’s on Halsted at 18th, and man, is he right. I’ve had both the chocolate tres leches and the coconut- both had me moaning and groaning in delight… and I’m not a sweets person. They keep banker hours as far as I can tell, so come out for lunch.
The truth of the matter is that while Chicago has pretty good Mexican (better than Texas where I grew up), it really does the country-wide typical dishes. Not many regional specialties (although I just found out about a cemitas place), more disappointingly not any seasonal specialties (I had to make my own chiles en nogada, which took me 7 hours standing up), and really no comida corrida favorites- which I think typify Mexican cuisine due to their homemade and every changing menus, as well as being everywhere in central Mexico.