Frontera Fresco - Chipotle Chicken Tamale ($3.95)
A late addition to the list, I honestly wasn't expecting a whole lot from Rick Bayless's quick-service outlet in Macy's. I assumed more care and attention was paid to the huaraches and tacos than anything as time consuming as tamales. I was wrong. The tamales at Fronera Fresco might actually be the highlight of the whole menu. Fragrant and light, they are beautifully presented and garnished with some remarkable salsa.
Bombon Bakery - Pork Tamale ($2.50)
Can a bakery make a great tamale? That was my bet, and Bombon Bakery delivered in a way I could hardly imagine. The tamales coming out of this West Loop joint manage a near perfect filling-to-masa ratio, making these some of the most satisfying examples in the whole city.
Tamales Lo Mejor de Guerrero - Green and Red Tamales ($1.50)
The smell of corn hit me the moment I walked in Tamales Lo Mejor de Guerrero—a small storefront in Rogers Park, and home to some of the best tamales in the city. I knew I was in for a good treat when I had to wait in a line that nearly stretched out the door, but I wasn't prepared for just how good these would be. That's especially true of the big, fat corn husk-wrapped ones, which featured a perfectly tender pork filling.
Tamales Lo Mejor De Guerrero, 7024 North Clark Street, Chicago, IL 60626 (map); 773-338-6450
Las Manas - Braised Beef Tamale ($6)
Honestly, I kind of wanted to hate on this one. Where most options I found were about a dollar, each tamale here goes for $6. But the organic creations from this Green City Market stall exhibit a lightness that no other place can match. I do miss the lard—butter and sunflower oil are used instead—but there is no doubt that these are some great tamales.
Las Manas, various locations; lasmanastamales.com
Maiz - Tamal de Elote with Spinach and Rajas ($5.75)
I'm still mourning the closing of Tamali in Bucktown, which, as the name suggested, specialized in tamales. But luckily the owner's original restaurant, Maiz, is still alive and kicking. On the recommendation from the waiter, I tried the fresh corn tamale topped with spinach and rajas—an inspired creation that was slightly sweet and spicy.
Tamal Oaxaca - Oaxacan Tamales
I had a surprisingly hard time locating a great banana leaf wrapped tamale. Most were either too meager or too dense. But the versions coming out of Tamal Oaxaca at the Maxwell Street Market were right on. A nearly fluffy masa gave way to juicy hunks of meat. They are only available on Sundays, but are definitely worth the trek.
Tamal Oaxaca, Maxwell Street Market, 500 West Roosevelt Road, Chicago, IL 60607 (map); open on Sundays
Tamales Garibay - Red Tamale ($1.75)
Relatively new on the scene, this spare little shop in Irving Park kicks out hefty tamales that are satisfying and wonderfully rich. The green ones are good, but the red ones seem to balance fat and heat the best.
The Tamalespaceship - (Two for $7)
These food truck owners take their tamales almost as seriously as they do their costumes. While just about everything I've tried has been good, I'm especially a fan of the ones with their complex mole they poured on top.
La Casa Del Pueblo Taqueria - Tamales ($1)
Like the grocery store of the same name located next door, everything about La Casa Del Pueblo is a step above the average taqueria. The steam tables are loaded with wonderful looking fillings, and the tamales are well made and filling, but still not too greasy.
El Milagro Tortilleria - Tamales ($1)
Though it's owned by the same people behind some of the best corn tortillas in the city, tacos are not the focus of this joint. Instead, spring for the affordable tamales, which are very similar to the kind found at La Casa Del Puebla, if a touch fattier.
Estrella Negra - Spinach and Artichoke Tamales (three for $8.00)
Like everything at Estrella Negra, you need a sense of humor to totally get the spinach and artichoke tamales. Instead of foisting another spinach artichoke dip on customers, Estrella Negra stuffs both inside a tamale. But instead of gloopy and heavy, the result is balanced and relatively restrained.
Frontera Grill - Tamal de Hongos y Queso ($9.00)
Of course, Frontera takes the time to do things right. The most artfully presented (my sincere apologies for the bad picture), this banana wrapped tamale comes with mushrooms and cheese. But at the center is an absurdly tender tamale (my fork didn't so much as slide through as free fall). All the toppings only added to the thrill, with a rich guajillo salsa offset by sweet little pea shoots.
Manolo's Tamales - Red or Green Tamales ($.85 a piece)
Much like Tamales Lo Mejor de Guerrero, Manolo's Tamales is a small storefront with a steady line of customers getting tamales to go. Though I'm using capable of dealing with the spiciest of meals, the spicy tamales here have a genuine kick. Be careful.
Real Tenochtitlan - Uchepos Gratinados ($8)
I know, I know. This poor tamale looks absolutely drenched in cheese, sauce, and crema. But what if I told you that the dish was actually kind of light? That's all due to the fresh corn tamale underneath, which provides some much needed sweetness to balance all of the other ingredients.
Supreme Tamales - Prices Vary
Wrapped up in plastic, these have less to do with traditional Mexican tamales than they do with Chicago's own industrial past; made by machines, which combine a heavily seasoned ground meat mixture and cornmeal into a perfect cylinder, these can be found at any good hot dog stand, where they are used most famously as the filling for a Mother-in-Law. Though I try to keep my intake to a just a few a year, I have a strange infatuation with them and couldn't fathom leaving them off the list.
Supreme Tamales, available at various stands and grocery stores; supremetamale.com
Tamale Guy - Pork Tamales (Six for $5.00)
I had the word out for him. As anyone who has been to a bar around Bucktown and Logan Square knows, occasionally a man will drop by with a cooler full of freshly made tamales. He's hard to follow precisely, so I was worried that I wouldn't be able to track him down in time. I wasn't even looking out for him as I sat at The Whistler last weekend. Then I heard the call for tamales and immediately became excited. Sure, these aren't the best in town, but they do hit the spot, especially after a few drinks, and the surprise is half of the fun.
The Tamale Guy, various locations; @tamaletracker