The Run Down

Ask any group of Chicagoans about their favorite taqueria and you'll get different answer from each. For this guide, you're going to eat at a place that just might make the cut on your list of favorites. You'll then walk a few blocks to a laid-back brewery along the Chicago river with a history of experimental beers. The night ends across the street where the next generation of funny people are hanging out and performing improv.

1. Tacos @ El Tragon

2. Beer @ Off Color Brewing

3. Improv @ iO Theater

1. El Tragon

On the fringes of Goose Island’s industrial zone, we’re at the corner of Halsted and Division, which might seem like an odd spot to start a guide. Gas stations occupy two corners of the intersection, and a giant empty grass lot occupies another.

The area is easy to gloss over, but stick around for a bit, and you’ll start to notice a line of truckers, cabbies, and city buses parked alongside that empty grass lot.

This crowd is onto something, and if you follow them across the street, you’ll come to El Tragon, a taqueria hidden in a gas station parking lot.

Once inside, you’ll find owner and operator Gerardo Madrigal behind the counter. With just a few employees, he’s here from morning until night, serving a simple menu focused on fresh ingredients.

On the wall across from the counter is a quote from his daughter that reads, “I have taco energy.”  That’s what you’ll be feeling soon. It’s that happy feeling you get when you have an excellent meal, and it’s going to sustain us for the rest of the night.

While I could go on about how incredible the food is, the foodie crowd was already quick to cover it here and here soon after El Tragon opened in 2021. Not much more needs to be said other than all their words ring true.

Quality food like this doesn’t happen by chance. The reality is that this was 30 years in the making.

It started in 1989 when a 17-year-old Madrigal left his hometown in the highlands of Jalisco, a state located in the western region of Mexico.

He arrived in Chicago young, ambitious, and eager to work. Like the thousands who came before and the thousands that would come after, that meant toiling away in the back of restaurants taking on any job that needed to be done.

For over three decades, he took on every hospitality role you could imagine. But in the quiet moments, he held onto a dream of one day opening a place of his own.

After the arrival of his daughter, he would stay up with her, sharing his aspirations and mapping out plans to build something not just for himself but also for her.

Years would pass after he first conceived of the idea for El Tragon. He was waiting for the perfect time to open his restaurant, but that perfect moment never came. Life doesn’t make it so easy.

It wasn’t until a difficult separation and being unable to see his daughter as part of that process, did he finally lay all his chips on the table and sign a lease for an empty storefront inside a gas station.

His daughter, who was only a child when he first shared his plans with her, would almost be in high school before El Tragon opened its doors.

But here we are today, sitting in the El Tragon dining room. His daughter, who he has since been able to reconnect with, is in the corner of the restaurant and part of his life again.

I think this is what people mean when they talk about chasing dreams. This is no overnight success, no lucky break. This is a culmination of Madrigal’s decades of hard work and experience, and you can sense it in every part of the dining experience.

2. Off Color Brewing (Mousetrap)

Along the Chicago River, just a few blocks north of El Tragon, you’ll notice a completely different scene. New luxury condo high-rises tower over the area, and there’s a constant presence of cranes as new mega-developments and construction projects redevelop the North Branch of the Chicago River.

Amidst all that is Off Color Brewing, our next stop.

The place is BYOF, so feel free to bring food from El Tragon and pull up a seat in their 150-capacity tap room. Initially opened in 2017, this space was designed for Off Color’s small batch experiments. So you’ll find beers created with all different types of fermentation techniques, vessels, and ingredients.

For those who enjoy the science and process of brewing beer, their blog takes you deep behind the scenes.

One thing you’ll notice about their beers is that they’re often named and created with a specific situation in mind. You’ve got Beer for Lightweights, Beer for Dealing With Your Family, Beer for Burgers, and lots more.

But if you’re bringing in food from El Tragon, Beer for Tacos is the obvious choice.

As described on their website, it’s a “blend from two different beers and then refermented with lime. The base beer is fermented with a Belgian yeast strain and spiced with coriander, while the second beer is fermented solely with Lactobacillus. Lactobacillus adds a refreshing tartness to the beer. While the Lime juice adds a bright acidity in its own right.”

In my own layman’s description, it’s an excellent wheat beer version of a lime margarita.

3. iO Theater

After loading up on tacos and beer, head across the street and cap off the night at iO Theater, which, along with Second City, is one of the two titans of the Chicago improv scene.

For years, iO operated out of a small space in Wrigleyville, where alums like Tina Fey, Amy Poehler, and Jason Sudeikis built their comedy creds. They moved to this giant theater complex in 2014, and it was meant to be a shiny jewel signaling iO’s bigger ambitions to the entire world.

But after unexpected construction costs and a pandemic, the original owners closed the theater after nearly 40 years in business. It looked like the end for iO, but just a few months later, the theater was sold to a pair of Chicago real estate executives who wanted to revive it for a second act.

iO reopened in late 2022 with a completely renovated space and a new creative team.

The theater is not just a theater anymore. The main level is an expansive bar where you can hang out whether or not you’re watching a show. Wood paneled walls and a retro color scheme make it feel like you’re on the set of a 70’s sitcom.

An extra bar on the second level caters to the smaller theaters upstairs.

When you’re ready to catch a show, you’ll find them in one of four different theaters. You’ve got a mix of open mics, stand-up comics, sketch shows, and various forms of improv, all with some wacky twist. Want to see improv in the form of Shakespeare? You’re in luck; they’ve got a show for you.


The night doesn’t have to end after your first show. Wander around, grab another drink at the bar, and check out the action happening the rest of the night. Maybe you’ll find an open mic and tell a couple of jokes, or perhaps the bar will fire up the karaoke machine as things close up.