Plain Chili at Ramova Grill ($3.85)
Chicago may not be the best chili town, but there is one bonafide chili parlor I'd stack up against any place in the country. Ramova Grill is a no-frills joint in Bridgeport, with a standard menu of diner classics. But the chili is taken seriously, even if doesn't taste like any chili you've had before. In fact, inspiration comes less from Texas and more from Cincinnati. There isn't much of a chile profile, but it's replaced by a spice blend, which is fragrant and haunting. (Rumors claim that cinnamon and allspice are involved.) The meat is ground and very tender, and there is little to no tomato present. It's one of the most unique bowls of chili I've encountered, and also one of the tastiest.
Cup of Plain Without Beans at Lindy's Chili ($2.89)
It's clear from the very first bite that Lindy's has a lot in common with Ramova Grill, except that there is a much stronger tomato presence. Personally, I think it also makes it harder to discern the individual spices, though I did appreciate that it had more heat. Still, I feel like I'm damning this with faint praise, even though it was one of the better bowls I encountered. I will say that this is probably closer to traditional chili than Ramova, so if you're looking for a introduction to Chicago chili, this is the perfect place to start.
Cup of Texas Steak Chili at Harmony Grill ($4.00)
Harmony Grill is basically just a diner for Schubas—one of Chicago's celebrated music venues. Which is another way of saying that this was one of the last places I expected to find a great bowl of chili. But the chili is cared for. Featuring hunks of a tender beef and a vibrant chili base, it's warming in the way great chili should be. The tortilla chips are welcome, if kind of superfluous. It's all about the chili here.
Regular 3-Way Cincinnati Chili at Chili Mac's ($5.95)
This Cincinnati-style chili parlor is often mentioned as one of the best in the city, but I wondered if it was just considered that because it was the only one serving up this distinctive style. I knew that the only way to know whether it really stood up to the real thing was to find a transplanted Cincinnatian and see what he thought (preferably one that worked at Skyline during high school). That's exactly what I did. While missing some of the secret spices, he did admit that Chili Mac's was good enough to satisfy all but the most intense cravings he had for his hometown's chili. That's more than good enough.
Brisket Chili at Chicago Q ($10.25)
This was the last dish I was expecting to fall for at Chicago Q—the Gold Coast barbecue joint. Even though there was a rack of the (very) expensive "competition ribs" on the table, the seasonal chili was the star. Featuring hunks of tender brisket and a warming chili base, this is a dish I wish they'd put on the menu permanently.
Cup of Chili (Without The Works) at Hawkeye's Bar & Grill ($2.50)
A total surprise. As something of the official UIC sports bar, I didn't expect the Hawkeye Grill to have a chili worth including here. But the cup I encountered featured tender ground beef, a decent spice blend, and not too much tomato. Though it lacks the complexity of Ramova or Lindy's, this was one solid and satisfying cup.
Cup of Black Bean and Beef Chili at The Brown Sack ($4.00)
Like everything at The Brown Sack, the chili here feels old school. There are no tricks here—just a satisfying bowl that will warm you up during the coldest stretch of Chicago's winters. Balance is part of the key. Though there are beans, there aren't too many of them. And while tomato is featured prominently in the liquid, there is enough heat to stand up to it.
Texas Chili at Porkchop ($4)
Though I wish the hunks of beef were a little more tender (these were a little too toothsome), Porkchop's Texas Chili made the cut thanks to its rich chili base. Rich and slightly spicy, almost anything would taste good in that bowl. Even the presence of beans couldn't get in the way of it.
Texas Roadhouse Chili at Heaven on Seven ($9.95)
I knew that Heaven on Seven had Creole and Cajun classics covered, but I was surprised to find a Roadhouse Texas chili on the menu. The beef is good, even if I wish it was a little juicier. But that's more than made up for by the thick chili base. Each spoonful brings on a warm glow of heat that lingers for minutes. Though I was concerned by the salsa and dollop of sour cream, both actually worked well in the bowl.