By OnMilwaukee Staff Writers   Published Oct 12, 2011 at 9:04 AM Photography: Andy Tarnoff

For the fifth straight year, October is Dining Month on, presented by Concordia University. All month, we're stuffed with restaurant reviews, delectable features, chef profiles and unique articles on everything food, as well as the winners of our "Best of Dining 2011."

There's a lot chili in this town, but two Milwaukee places are iconic in this category. In the middle of Dining Month at, we put them to the test.

The results weren't even close, with Real Chili's thick and spicy chili garnering every vote except one, making it the clear winner. But some of the judges weren't all that impressed with either.

Tim Cuprisin
Media columnist
Pick: Real Chili 
Really, this wasn't much of a competition – and that's not really a slam against Webb's chili. It's clearly comfort food. But it's not the kind of chili that creates enthusiasm in college students who still seek it out 20 years later. The Real Chili chili has distinct flavors that aren't like Cincinnati chili – or any other town's. It's a true Milwaukee variety, with a distinctive broth richly flavored by chili powder, offering enough spice, but not an overpowering bite. It's not the beans and noodles that are the main draws, It's the "real" chili. This is one place that lives up to its name.

Damien Jaques
Senior contributing editor
Pick: Real Chili
I would not order either of these chili offerings. Both seem designed to be unoffensive and appeal to the lowest common denominator of customers. Good chili has a palette of complementary flavors that can include sweet and savory.

Webb's chili is watery and nearly devoid of any flavor. Real Chili is better but disappointingly minor league. Come on, guys, make my mouth explode!

Renee Lorenz
Pick: Real Chili
I was initially turned off by the consistency of Webb's chili, which was more like soup than chili. Besides that, both consisted of pretty much the same ingredients, with the only exception being the ground beef, which was chunkier in the Webb's chili and more mixed into the Real Chili offering. In taste, Real Chili won by a landslide. It was obvious that Real Chili contained actual spices, while Webb's really only tasted like the main ingredients. I wouldn't choose to go hungry if my only option were Webb's chili, but here Real Chili wins out.

Molly Snyder
Associate editor
Pick: Real Chili
I cannot deny that I have been a Real Chili fan for years, but I did go into this challenge with an open mind. I couldn’t remember if I’d ever tried a bowl of Webb’s chili, and I thought maybe, just maybe, it would rival Real Chili. But it didn’t. I found the Webb’s chili flavorless in comparison to the rich, spicy sauce in Real Chili. And in the end, I realized, it’s all about the spices and sauce because both chili have beans and meat. Although Webb’s was filling, it just wasn’t as tasty.

Bobby Tanzilo
Managing editor
Pick: Real Chili

Although the ingredients are much the same – spaghetti, ground beef and red beans – Webb's chili is brothy and almost soupish, and Real Chili's is much drier. The other difference? Webb's comes with Premium Crackers and Real Chili dishes up oyster crackers.

But the key is in the flavor and the lack of seasoning renders the Webb's chili rather pedestrian. The Real Chili is more seasoned – which is why I picked it – but having been a regular at WMSE's annual chili event I know Milwaukee really makes some stellar chili and neither of these is among them.

Andy Tarnoff
Pick: Real Chili

It's been a while since a Milwaukee Challenge was this cut and dried for me. Nothing against George Webb's chili. It’s fine. A little sweet, tomato-ey and watery, perhaps, but decent enough. But man oh man, Real Chili's offering is the best. Even though I typically doctor it up with cheese, onions and sour cream, it’s outstanding on its own. The mild version gets slightly spicy as you eat more. It’s so salty, meaty and flavorful, with just a hint of cinnamon, I want more just writing about it. Real Chili isn't just better than Webb's chili. It’s the best chili I've ever tasted. And it’s not just for breakfast anymore – or so says the bumper sticker.

Andrew Wagner
Senior Staff Writer
Pick: George Webb
Disclaimer: Yes, I appeared in a George Webb commercial. Fact: that had no bearing on my decision. With that out of the way ... This was no contest in my book. I've plenty of options plenty of times. In fact, I ate both offerings independently over the weekend preceding our challenge. I have nothing against Real Chili; it's good, it's filling, it's hearty but it's just a bit too dry for my taste. People try to tell me that it's similar to or better than my beloved Skyline Chili in Cincinnati, but it's not even close. Still, I still enjoy it and I'll frequently stop by for a bowl, but Webb's version is more my style. I like the soup-like consistency. I like the flavor. I like the sharpness, the tinge of pepper instead of the sweetness of cinnamon. Webb's chili has been my go-to since I was first old enough to go eat somewhere by myself. That won't be changing anytime soon.