The first time I used Craiglist was when I told a friend I couldn’t find tickets to a concert at the Double Door. She suggested I check on “,” which is how we referred to websites back then. I had no idea what she was talking about, but looked it up, and realized just how much things were about to change.

If you don’t remember when Craigslist first came out, you probably don’t understand how much of a big deal it really was. Suddenly, you had a central listing to buy and sell anything, to give things away, find jobs, or even make a missed connection. Granted, the last one was always weird, but other than that, it seemed great.

Using Craigslist for Chicago real estate deals back then seemed quick and easy. And, to many, it may still seem that way— I’ll tell you how to do it—but, it might pose more challenges than you imagine. Let me explain.

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Two Ways to Use Chicago Craigslist for Real Estate Deals

There are two primary ways to use Chicago’s Craigslist for marketing to distressed homeowners. One tries to get homeowners to contact you through advertising and the other amounts to fishing for leads on advertisements by others. Either one has a chance of being effective for finding Chicago houses to buy, rehab, and sell—if you’re willing to spend the time and energy.

Using Craigslist for Inbound Marketing

In theory, placing ads on Chicago’s real estate section on Craigslist is a great way to get eyeballs. After all, for the last couple of years, Craigslist was the 14th-most trafficked site in the US, with over 86,000,000 visitors a month. While you won’t find information about traffic by city, it stands to reason that a decent chunk of that comes from the Windy City.

After all, we have a robust real estate market and people selling their house on Craigslist are looking for buyers. So, you never know, these folks might be sitting at their computer right now looking through Chicago Craigslist ads for a real estate investor who can buy their house quick. If you have a good ad that gets a lot of attention, it stands to some reason that you will be able to get distressed homeowner leads coming to you.

The thing is, though, you have to create a really good ad, target it right, and keep re-upping it to account for the churn. And, then you have to hope that someone flickering their eyeballs over your ad makes the split-second decision to stop. You are going to be competing against everyone who wants to buy a house “the easy way.” The seller is going to be flooded with ads and it could be pretty random who they are going to trust.

Searching for Leads on Craigslist

This other method is also pretty straightforward. You can go to the Chicago real estate page on Craigslist and search for any type of property right now. Just looking at it today, I see everything from single-family homes in Evanston to 6-unit buildings in Lincoln Park and old sprawling houses in Austin-Gresham.

These are ads placed by homeowners who want to sell. And, you want to buy. So, you just need to pick up the phone and make the call. It seems almost as simple as the website itself.

And, that’s the first problem. Because of its simplicity, the website is a bit of a mess—chaotic, sprawling, hard to sort. Even if your search is filtered for “houses for sale by owner” specifically in the city of Chicago, you’ll get homes in Michigan and multi-story offices. Not only is the actual city filter wonky, but you also can’t search by Chicago’s up-and-coming neighborhoods individually.

So, finding what you want is going to take time. You probably are going to have to sift through a lot to find what you are looking for. And, in this business, time is always money.

Whether reaching out to a listing or being contacted by a potential lead, the overarching problem is that there isn’t really any moderation on Craigslist. There’s no way to tell what kind of house it is by an ad—or if the house even actually exists. There is a penalty for lying, but that can be easily overcome by switching accounts.

Craigslist is still great for some things—but not for finding Chicago real estate investment opportunities. You simply shouldn’t take the risk with your time and money when you have a better option.

Make Getting Chicago Real Estate Deals Easier on Yourself—Without Craigslist

There are a lot of ways to get real estate investment leads in this city. Some are good, but some—like Chicago foreclosure auctions—are less so. I’ve tried them all, believe me. But, the best strategy turned out to be the easiest: become an independently owned and operated HomeVestors® franchisee.

You’ve seen the “We Buy Ugly Houses®” billboards all around. In fact, I think there is one off the Edens, near that office building for sale. And, distressed homeowners see them too. They trust the nationally recognized brand and feel secure making the call when they need to sell fast.

As a HomeVestors® franchisee, I’m not just someone reaching out to them through Craigslist, a random email address in a sea of spam. And, I don’t have to wade through a thousand posts. I don’t have to hope that I’m the first person to contact someone who happens to have the right deal. It’s a qualified lead, delivered right to me.

A lot has changed in Chicago. The market has changed. Neighborhoods have changed. The Double Door is gone. But, what hasn’t changed is that we’re a city that operates on trust. And, the best way to establish that is to have the backing of the HomeVestors® national brand.

If you want a better way than Craigslist to get Chicago real estate deals, request information about becoming a franchisee today. It’s a connection you don’t want to miss.


Each franchise office is independently owned and operated.


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