2317 N Rockwell St Unit 2317.5-A1 Chicago, IL 60647

Meet the Pioneer Rental Experts – The Team That Helps You Rent Smarter

Finding the right place to live in Chicago can be overwhelming—but it doesn’t have to be. At Pioneer Realty Group, our rental team brings years of experience, real market knowledge, and a commitment to transparency that helps you move forward with confidence.

We don’t post fake listings, and we don’t use bait-and-switch tactics. What you see is what you get—real photos, accurate details, and agents who are here to help, not pressure.

Here’s who you’ll be working with:

Sean Flynt, our co-founder, has over 12 years of experience in leasing and property management. He’s built our entire approach around one goal: putting renters first.

Helen Bailey, co-founder and managing broker, combines her background in real estate finance with a passion for neighborhood-level impact—ensuring your rental process is efficient, respectful, and smart.

Savannah Whittington, a former educator turned real estate professional, knows how to listen, guide, and deliver. She started in rentals and has helped hundreds of renters find their home.

Ryan Anguilm, our Leasing Director since 2018, leads our day-to-day rental team and mentors agents to make sure every client gets top-tier service.

Matt Byrne joined Pioneer in 2019 and brings lifelong Chicago knowledge to every showing—he knows the best spots, the best deals, and how to match people with neighborhoods that fit.

Jon Hamilton, part of our team since 2017, has a strong background in property management and makes sure everything from application to move-in is smooth and clear.

We’re not just agents—we’re a team of trusted advisors who live and work in the neighborhoods we serve. Our goal is simple: help you find the right apartment without the stress, the fluff, or the runaround.

Search “Pioneer Realty Group Chicago” to learn more about how we work and meet the full team.

And while you're there, look for our Perfect Rent Finder—a quick, easy way to tell us what you're looking for and start your apartment search with our team today.