From a Family Dream to a Chicago Favorite: The Story of The Outpost Mexican Eatery

The Outpost Mexican Eatery began with something simple: a craving for really good tacos and a deep love for authentic Mexican food.

Founded by Anna Kamilis and her family, The Outpost was never meant to be just another restaurant—it started as a family investment rooted in South Side Chicago pride, where good food and strong community ties are part of everyday life. What began as a shared idea quickly turned into a passion project, and eventually, a full-scale restaurant built from the ground up.

A Concept Born Before a Crisis

In late 2019, Anna and her family began developing The Outpost concept alongside local chefs with Mexican roots, drawing inspiration from traditional family recipes and fresh, simple ingredients. The goal was to create something authentic, fast-casual, and memorable.

But just as plans were coming together, the pandemic hit—forcing the entire industry into uncertainty.

Pivoting Through the Pandemic

Like many small business owners, Anna was faced with a defining decision. She left her outside sales career and committed fully to The Outpost, shifting operations overnight to curbside pickup, delivery, and eventually a pioneering cold meal delivery model.

With the help of her family, she even handled deliveries personally—doing whatever it took to keep the business alive during one of the most challenging times for restaurants.

Growing Through Challenges

Despite the uncertainty, The Outpost didn't just survive—it grew.

The team opened a location in Downers Grove during the height of the pandemic, building strong community ties that continue to support the brand today. That connection with customers and surrounding neighborhoods became one of the driving forces behind the restaurant's expansion.

In 2024, The Outpost opened its flagship location at Two North Riverside Plaza, a milestone that marked how far the family-run concept had come.

Even through challenges like construction disruptions at their Harrison-area location, the business continued to thrive thanks to loyal customers, courthouse regulars, construction workers, and catering partnerships with major companies like Pepsi, Walgreens, and BMO.

A Female-Owned Business Built on Resilience

At the heart of The Outpost is a female entrepreneur leading with resilience, determination, and vision. Anna Kamilis has built her business in an industry known for its challenges—balancing rising costs, staffing pressures, and constant change—while staying grounded in quality and consistency.

Her leadership style is direct and hands-on, ensuring that every location maintains the same standards while empowering team members to bring their own creative touch.

What Makes The Outpost Different

The Outpost isn't a franchise or corporate-backed chain. It's a family-owned restaurant built on values that set it apart:

• Fresh, scratch-made food with house-made seasoning
• No preservatives, no lard, and gluten-free options
• Strong ties to local vendors and community organizations
• Loyal customers who have supported $2 Taco Tuesdays through industry changes
• A team culture built on long-term staff and shared ownership

More Than a Restaurant

Beyond food, The Outpost is deeply involved in the community—supporting local schools, women's shelters, and organizations like Dress for Success. The team also participates in fundraisers, educational programs, and speaking engagements, sharing their story with the next generation of entrepreneurs.

Looking Ahead

As the food industry continues to evolve, The Outpost is focused on growth in catering, delivery, and accessible dining—offering value without compromising quality. Whether serving a family of six or an individual meal, the mission remains the same: fresh food, fair pricing, and strong community connection.