When real estate investors first started discovering the internet, back in the late 90s, a lot of old-timers—think classic Chicagoans, thick accents, and thicker mustaches—dismissed it. Me, I was no tech genius, but I knew that a smart real estate investor should use any resource that could benefit their business.

As it turned out, decades later, nearly all of your Chicago real estate investing can be done online. And as we’ve learned from a pandemic, sometimes virtual real estate investing is a necessity.

If you have the right tools and resources, you can make online investing work for you. You can find leads, complete the needed paperwork, and even find buyers online. These are all great tools, and the best way to make them work is to have them all in place when you need them. Being able to use all of these tools makes online real estate investing in Chicago work for you.

Chicago real estate investing online

Understanding Online Real Estate Investing in Chicago

There are some jobs that change fundamentally when they move online, and some jobs that barely change at all. Real estate investing is in the latter category. Even if your day-to-day seems different, the purpose and the principles remain the same. 

You’re still hustling for leads. You’re still trying to find houses that you can buy at a low price and turn around or rent out as quickly as possible. You’re still working to understand the market. And you still have to make connections with sellers and close the deal. 

The only difference is in how you’re doing it. You’re doing it from home or even from your phone. And that can add some complications. 

Being online can make it harder to make those connections. It can be more of a challenge to inspect the house. It can be more of a challenge to find buyers. 

But it needs to be done, maybe now more than ever. We know that Chicago real estate investing during COVID-19 has presented some great opportunities. Because of these opportunities, online real estate investing is here to stay.

So whether you’re starting real estate investing during the pandemic or adjusting your existing business to the new reality, you need to know the best ways to make this work. 

Ideas and Resources for Investing in Chicago Real Estate Online

I’ve come to the belief that online real estate investing is great, especially here in Chicago. Think about it: the city is way too big to cover physically. But by perfecting my online investing skills, I can be working in Rogers Park and Hegeswich on the same day. I can be buying in the up-and-coming Humboldt Park and selling in Calumet without leaving my desk. 

But I need to do it right. Here’s what I’ve learned. 

Connections Matter More Than Ever

I have a pretty diverse business—I do a lot of fix-and-flip, but will also wholesale in order to keep revenue coming in. Wholesaling demands a network of buyers so that you can turn something around quickly (making sure one follows the Illinois real estate wholesale laws). 

One way to do that online is see which Chicago real estate meetups are virtual. Most of the smart ones have figured out a way to transition, so you could look for the ones that are particularly active. These aren’t just good for buyers, of course. They are also great ways to see how other investors are adjusting, exchanging information, and finding contractors who can move fast without a ton of supervision. All of these connections matter.  

Invest in Helpful Tools and Resources

There are certain tools that you’ll need to successfully invest in Chicago real estate online: 

  • A reliable video platform: We’re probably all familiar with platforms like Zoom by now. You’ll need to have a solid connection and clear video to make connections, inspect houses, and to sell. This is non-negotiable. 
  • Electronic signing tools: You may not ever meet face-to-face with your seller or your buyer. You’ll need tools like LexCheck to conduct the contract negotiation process online. 
  • Training courses: There are a lot of gurus and teachers out there who can help you invest online. Of course, the best way to learn is to have a dedicated mentor who is working with you, not just lecturing through a pre-recorded video. 

Lead Generating Still Follows the Same Rules

Like mentioned before, the fundamentals of the business have not changed. The most important thing to know is that you can’t afford to waste time. And as anyone who has gone down a Wikipedia rabbit hole can tell you, being online can be dangerous if you can’t manage your time. 

So even though you are searching for leads online, you can’t change your methods. Craigslist Chicago real estate is still a dead end. Paying brokers can work, but they are working with the same limitations you are. Social media like Instagram can be fun but isn’t really a great way to find leads or sell your house.  

You still need to maximize your chances of getting great leads without spending a lot of time sifting through nonsense or not getting value for your spend. That’s hard when you don’t really have a way to mingle. But it can be done. 

In fact, all of this can be done. There’s a way to make it really work for you. 

The Best Way to Invest in Chicago Real Estate Online

When I first became an independently owned and operated HomeVestors® franchisee, people asked if that meant I was working for someone. But it was just the opposite. I was still fully independent, but had the support of a nationally-known franchise. It was like having my own clout at City Hall. 

This has been especially important in the era of online. With HomeVestors®, I have a whole network of other investors who are ready to sell and who understand the market. I have a ton of tools, like a hard money lender portal and an investment valuation tool that helps me keep my finances in order. There are even dedicated mentors and comprehensive training resources, good at any time (but especially for those starting out). 

The best part is probably the leads. People in Chicago know HomeVestors®. The “We Buy Ugly Houses®” ads are all over the city. So when people need to sell fast, they call HomeVestors®. The sellers call HomeVestors® and can be routed directly to me and I get a really good lead—someone who is ready to sell. Working with a known company is a huge first step in establishing trust, which is even more valuable during an era away from face-to-face. 

I admit I miss those old-timers who loved this city with a rough passion. But they were wrong about some things. About half of them were wrong about which baseball team to support (I’ll let you guess), and they were all wrong about the internet. You can do great things online in Chicago working with real estate investment opportunities. If you want to be on the right side of this, request information about becoming a franchisee today


Each franchise office is independently owned and operated. 


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