Chicago's Top 5 Real Estate Podcasts in 2026

I hope you have some takeaways from this blog. if you want our team to provide you tenant placement or property management. Click Here
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Feedspot refreshed its ranking of the best Chicago real estate podcasts on August 1, 2026, and it is a genuinely useful list. Eight shows made the cut. I want to walk through the top five, counting down from number five to number one.

Full disclosure before we start. Our show, Straight Up Chicago Investor, is on this list. So rather than rank these by my own opinion, which would be worthless to you, I am using Feedspot's order exactly as published. They score shows on relevance to the category, authority, audience engagement, ratings and reviews, listener counts, and publishing consistency.

What I like about this particular list is how little overlap there is. These five shows are not competing for the same 45 minutes of your commute. One is commercial law, one is corporate real estate, one is brokerage, one is community, and one is residential investing. If you work in Chicago real estate, there is something here for you no matter which side of the business you sit on.

Key Takeaways

• Feedspot's August 2026 ranking of Chicago real estate podcasts lists eight shows. These are the top five.
• The order is Real Estate Moguls at five, Laricy LIVE at four, CoreNet Chicago at three, Real Estate for Breakfast at two, and Straight Up Chicago Investor at one.
• The five shows cover very different niches: residential investing, commercial real estate law, corporate real estate, residential brokerage, and industry community.
• Episode lengths range from about 23 minutes to a full hour, so there is a format that fits whatever your day looks like.
• Rankings get refreshed periodically, so the order you see today may not be the order six months from now.

5. Real Estate Moguls

Produced by VibeSociety, Real Estate Moguls takes a different angle than most shows in this space. Instead of focusing narrowly on investors, it pulls in the whole ecosystem: brokers, lenders, attorneys, inspectors, developers. The premise is that real estate is a team sport and the industry works better when the people in it actually know each other.

Episodes run about 23 minutes, which makes it the quickest listen on this list.

Find it: tfocb.com | Apple Podcasts | Spotify

Listen if: you are building a network in Chicago real estate and want to understand what the other roles in a transaction are actually dealing with.

4. Laricy LIVE

Matt Laricy is one of the highest producing residential agents in the city, and Laricy LIVE is where he breaks down market trends, industry news, and the questions clients keep asking. It is a weekly show with a brokerage lens rather than an investor lens, which makes it a good counterweight if you spend most of your time on the investment side and want to know what is happening in the owner occupant market.

Episodes typically run around 32 minutes.

Find it: mattlaricy.com/media | Apple Podcasts | Spotify

Listen if: you want a current read on the residential market from someone doing serious transaction volume in it.

3. CoreNet Chicago

This one comes from the Chicago chapter of CoreNet Global and covers corporate real estate, which is a corner of the industry most investor focused podcasts never touch. Each installment features new guest speakers on whatever is moving in the corporate occupier world.

Episodes tend to run about an hour, and the publishing schedule is monthly rather than weekly.

Find it: soundcloud.com/corenet-chicago | Apple Podcasts

Listen if: your work touches office, corporate tenants, or the institutional side of the business, or you are just curious how the big end of the market thinks.

2. Real Estate for Breakfast

Phil Coover has been putting out Real Estate for Breakfast since January 2017, which makes it one of the longest running Chicago real estate shows out there. It sits at the intersection of commercial real estate and law, bringing on professionals and attorneys to work through the complicated stuff: deal structures, current developments, problems that do not have clean answers.

Episodes run about 41 minutes and it carries a 5 out of 5 rating on Apple.

Find it: realestatebreakfast.com | Apple Podcasts

Listen if: you are on the commercial side, or you are a residential investor who has started running into legal questions your gut cannot answer. Coover's show will make you smarter about the paperwork.

1. Straight Up Chicago Investor

This is ours, so take my description with the appropriate grain of salt and just go listen for yourself.

Tom Shallcross and I started Straight Up Chicago Investor in 2020 to do one thing: break down what it actually takes to own and operate rental property in this specific market. Neighborhood by neighborhood, ordinance by ordinance, deal by deal. Chicago is not a market you can learn from national content, because almost nothing about the RLTO, the Cook County RTLO, or the way this city handles a turnover translates from anywhere else.

We are at episode 470. Full episodes drop every Thursday and run about an hour with a guest who owns, builds, lends, litigates, or manages here. Every other Tuesday we put out a Straight Up Tuesday Tip, which is 15 minutes on a single idea. The show holds a 5 out of 5 rating across 278 Apple reviews, and episode 500 lands in December 2026.

Find it: straightupchicagoinvestor.com/podcast | Apple Podcasts | Spotify | YouTube

Listen if: you own rental property in Chicagoland, or you are trying to buy your first one and do not want to learn the hard lessons on your own dime.

The Short Version

If I had to give one piece of advice on how to use this list, it would be this: do not just subscribe to the show that matches what you already do. The most useful episode you hear this year is probably going to come from the corner of the business you understand least. Investors should be listening to the commercial and legal shows. Brokers should be listening to the investor shows. That is where the blind spots are.

FAQ

Who put this ranking together? Feedspot, a content discovery platform that maintains ranked podcast lists by topic and region. The Chicago real estate list was last updated August 1, 2026.

How does Feedspot decide the order? It is a blended score covering relevance to the category, authority, social following, engagement, ratings and reviews, listener counts, and how consistently the show publishes. No single metric decides it. 

Feedspot is an RSS Reader that lets you follow your favorite podcasts alongside blogs and news in one place.

Are there other Chicago real estate podcasts worth hearing? Yes. Feedspot's full list runs eight shows deep and includes the Chicago REALTORS Young Professionals podcast, Ten with Ben, and LUXE Life by Jennifer Williams. Worth a look if the top five do not scratch the itch.

Will this ranking change? Almost certainly. These lists get refreshed on a regular cycle, so treat this as a snapshot of where things stood in August 2026.

Listen or Watch

If you want to start with ours, listen on Apple Podcasts, Spotify, or wherever you get your podcasts. Every episode is also up on our YouTube channel if you would rather watch than listen.

The full archive, sorted by neighborhood, strategy, and topic, lives at straightupchicagoinvestor.com/podcast.

And if you know someone in this market who would make a great guest, reach out to us here. Some of our best episodes came from a listener making an introduction.

Free Rent analysis

Schedule a call