It’s not a big deal. Really. I mean, unless you’re a fan of hot soup on cold days…and figuring out which chef in Lakeview has mastered the art of warming you up against the cold Chicago winter (or early fall, in this year’s case). If you are, though, this might be the most thrilling day of your life: it’s the Lakeview East 2019 Jack Daniel’s Chili Cook-Off

With chefs from 13 restaurants around Lakeview participating, this year’s cookoff has reached new levels of competition. At risk of making you drool all over your computer screen, I want you to just imagine with me for a moment the tangy, smoky flavor of Wrigley BBQ wrapped up in a bowl of chili. Now walk with me into the beautiful, trendy Big Star and think tacos meet chili. Don’t eat meat? Oh, honey. The Chicago Diner is gonna be there too, comin’ in strong with a chili that’ll knock even the staunchest of carnivores right off their feet. Okay, I’ve officially reached drool emoji levels.

Here’s the thing, too, about this chili cookoff. Because the citizens of Lakeview East are of a democratic nature, we’re letting the people decide who makes the best chili in the land (or at least the neighborhood, okay?). You buy a ticket and you get to sample all of the chili (from thirteen vendors, no less) to pick your favorite. Need to cleanse your palate? We thought you might. That’s why we asked our friends at Jack Daniel’s to put together some drink samples and cocktails for you to enjoy. You sold? Yeah, we thought so. Here’s what you need to do to prepare yourself for this blood…er….chilibath. 




      1. Prepare your tastebuds.

We take things pretty seriously here in Lakeview East. Prepare your palate by staking out the participating restaurants to get a gauge of what these chefs are capable of and what to expect. Here’s your list:

Houndstooth Saloon

The Chicago Diner

El Mariachi Tequila Bar

ROCKS Lakeview

Wrigley BBQ

Drew’s on Halsted

Hutch American Bistro

Deuce’s Major League Bar

Big Star

Kubo Chicago

D.S. Fajita Factory

Trader Todd’s

Rizzo’s Bar & Inn


      2. Re-watch that classic chili scene from The Office. 

If you know, you know. If you don’t, check out episode Casual Friday (S5,E26). 

      3. Determine who among your friends is worthy to help you make this decision.

Must have incredible endurance, the palate of a Michelin-starred chef, the spirit of a wild eagle, and a taste for good drinks. Choose accordingly. 

      4. Show up at Sidetrack on Saturday, November 16 from 1-5p.m. with your game face on.

Get your ticket here!


Written by Laura Scherb from Page & Plate

See Laura’s Blog and more great content from her here!