Chilaquiles Verdes at Topolobampo ($14)
Looking for the most elegant and complex version of the dish? Look no further than Rick Bayless's high-end restaurant, Topolobampo. Instead of triangles, the tortillas are thinly sliced and fried until crispy. When mixed with the roasted tomatillo sauce, they take on the characteristics of al dente pasta. You better believe there is a fried egg on top, but the rest is unexpected. Wilted spinach gives the dish body, while some fried onions lend more crunch. The only real issue is that the dish is only available for lunch. Plan accordingly.
Chilaquiles En Salsa Verde Con Huevo at Huaraches Doña Chio ($5.75)
This is the second time I've placed a bet on Huaraches Doña Chio and won. As you'd guess from the name, the Edgewater joint is best known for its huaraches—great, plate-sized discs of masa topped with all manner of things. Since each is prepared from scratch using fresh masa, I guessed that the tacos were worth trying. They were. Now, I can also confirm that the chilaquiles are also worth your time. Instead of turning to mush, the tortillas maintain their structure when mixed with the tomatillo sauce. Some crema, a couple fried eggs, and some incredible refried beans round this meal out nicely.
Huaraches Doña Chio, 1547 West Elmdale Avenue, Chicago, IL 60660 (map); 773-878-8470
Braised Pork Chilaquiles at The Bristol ($12)
"A heaping mound of baked chips is saturated in a smoky chile sauce and layered with braised pork shoulder and a few slabs of braised pork belly. The chips are cooked just to the point of being fork-tender without becoming mushy, making it all too easy to shovel large amounts into your mouth at a time. An ample dosage of queso fresco, chopped raw onions, and cilantro freshen things up, and the whole thing is adorned with a sunny-side up egg, which when pierced, escalates the whole thing in the very best pasta carbonara-like way." Read more here >>
Chilaquiles at La Casa De Samuel ($5.25)
Considering how great the tortillas are at this Little Village spot (and they might be the best in the city), this was on the top of my list of places to try. Sure enough, the chilaquiles are built on a foundation of firm and crunchy tortillas chips, which manage to hold their integrity in the face of the sauce for quite a while. That would be enough to recommend, but the addition of the restaurant's truly stunning grilled cecina—a salty cured beef—makes this dish sort of essential.
Chilaquiles at Au Cheval ($17.95)
Leave it to Au Cheval to go up to the absolute edge of ridiculous. Even if you order the smaller size, the result is messy and completely out of control by design. Loaded with guacamole, sour cream, pickled red onions, sliced jalapeños, and some of the softest, creamiest scrambled eggs I've ever encountered, these are the closest to gut-busting nachos as any you'll find on this list. In fact, the sauce is served on the side, so you can adjust how much of it you'd like to add. While most chilaquiles are meant as a filling, if still respectable, breakfast, this gut-busting dish is ideal late night revelers in need of something to soak up some alcohol. That explains why most days of the week you can't order a plate of these until after midnight. Fortunately, you can also score a plate for weekend brunch.
Chilaquiles Con Huevo at Taqueria Moran ($6.50)
Looks like I owe Taqueria Moran an apology. When I visited the Logan Square taqueria for Chicago Tacos, I praised the adobado tacos, but kind of dismissed everything else on the menu. I was wrong. Turns out that you can find a remarkably solid plate of chilaquiles here, too. Instead of piling on the cheese and crema, this plate is straightforward and satisfying—the opposite of over the top.
Taqueria Moran, 2226 North California Avenue, Chicago, IL 60647 (map); 773-235-2663
Wood-Oven Chilaquiles at Xoco ($6)
"Soft-scrambled eggs and totally melted cheese blanket the top, with minced onion and cilantro; bits of them creep down into the corn chips, smothered in a fresh, spicy tomato-serrano sauce, so that the middle chips dissolve into soft layers of corn tortilla but the outer edges stay crisp. Heated in the wood-burning oven, it's as warming and stomach-satisfying as it gets: hearty enough to get you going, spicy enough to enliven the dish without wreaking more havoc on an unsettled stomach." Read more here >>
Chilaquiles at Nuevo Leon ($4.75)
Though it's on the breakfast menu, you can score the chilaquiles any time you want. Why would you? Though I'm a genuine fan of Nuevo Leon, a Pilsen stalwart that has been around since 1962, I would never accuse any dish there of being light. For the most part, this is filling, hearty food, and there is nothing wrong with that. But the chilaquiles are downright reasonable. The bright and spicy sauce livens up the plate, making the earthy, creamy beans taste even better than usual.