06.11.2025 PropStream
Disclaimer: PropStream does not offer investing advice or make profit promises. This article is for educational purposes only. We recommend consulting financial professionals and/or doing your due diligence before investing in Midwest real estate.
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Key Takeaways:
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One of the best indicators of a strong real estate market is a business-friendly climate.
When cities attract companies through pro-growth policies and incentives, they don’t just gain employers—they gain jobs, people, and long-term economic stability. This fuels steady housing demand and tends to push property values and rents upward.
Below, we’ve ranked the five most business-friendly cities in the Midwest, along with why they offer strong real estate investment opportunities.
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1. Chicago, Illinois
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Chicago is both the Midwest’s most populous city and its most business-friendly market.
In 2024, it had the most startups and Fortune 500 companies. It also had the highest growth in the number of startups over the last five years, the highest level of exits, and the highest number and size of $50M+ exits and raises.
Furthermore, Chicago has access to many human and capital resources. It has 29 universities, including the University of Chicago and the Illinois Institute of Technology. Additionally, the city ranks first for the number of venture capital (VC) investors, total amount invested by VCs, number of angel groups and angel investors, and number of accelerators and incubators.
Finally, Chicago is well-connected. Among Midwest cities, it has the nearest airport, the most nonstop flights, and the most interstate highways and population within a 125-mile radius.
As a real estate investor, these attributes are a recipe for housing market stability and growth. For example, they help explain why Chicago home prices have been on a steep climb over the last few years and why rents have increased 41% in less than a decade.
2. Minneapolis, Minnesota
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Minneapolis is another major business-friendly market. Among Midwestern cities, it ranks second across each of the following: most startups, most Fortune 500 companies, most VC investors, most invested by VCs, most angel investors, and most accelerators and incubators.
In other words, like Chicago, Minneapolis is a hotspot for growing businesses. This attracts employers and workers who then increase demand for housing. So far, demand has outpaced supply. In May 2025, there were only 2.4 months of inventory, while the median home sales price hit $400,000, up 2.8% from last year.
3. Indianapolis, Indiana
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Indianapolis is the capital and most populous city of Indiana. It’s notable for offering businesses the most government support among Midwestern cities. Additionally, it’s relatively tax-friendly. For example, Indiana is one of only twelve states with a corporate income tax rate below 5%.
Naturally, these perks have boosted the local housing market. In fact, it was named one of the hottest housing markets for 2025, with housing prices predicted to rise by 3.4% during the year.
At the same time, housing is relatively affordable, with nearly 42% of the area’s housing stock priced below $236,000. This is impressive, given how fast the area is growing: From April 2020 to July 2024, it gained 85,000 residents, a majority of whom came via international migration.
4. Pittsburgh, Pennsylvania
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Pittsburgh is the smallest city on this list with a population of just over 300,000. However, it ranks third for the most startups and most VCs and second for best university ecosystem, which includes Carnegie Mellon University, known for its computer science and robotics programs.
At the same time, Pittsburgh is highly affordable. In 2025, Pittsburgh was named the most affordable U.S. housing market, with a median list price of $229,000, less than half the national median of $490,000. So if you want to tap into a growing market with a low barrier to entry, Pittsburgh may be a great place to start.
5. Columbus, Ohio
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Last on our list for business-friendly Midwest cities is Columbus, Ohio. It ranked third across most $50M+ business exits and raises, most invested by VCs, and most angel investors. This and the area’s rapid population growth make it a popular real estate market among investors.
In April 2025, the median home sale price was $320,000, up 0.8% from last year. Meanwhile, the median days on market was 32, which means sales are moving quickly. However, inventory is limited. In March 2025, there were 1.8 months of supply, up 38.5% from last year.
Use PropStream to Find Off-Market Leads in the Midwest
Now that you know where some of the top real estate opportunities are in the Midwest, the next step is to hone in on specific neighborhoods and properties. If you’re relying on just the MLS or public records, this can be overwhelming. Instead, PropStream it!
Our platform has over 160 million off-market property records that you can filter across 165+ categories, including pre-foreclosures, vacant properties, tired landlords, and more. From there, you can create, save, and automatically update lead lists to maintain a steady stream of investment opportunities tailored to your strategy.
