investing in chicago

Hi chicago investors! im new to the web site but have been an rei exclusively since 1998. my current area of focus is preforeclosures. just want to hear from other chicago investors old and new to swap stories, ideas, and who knows, there is a world of possibilities!


Similar situation.

Are you doing this downtown?


In my opinion there is no resonable way for average investors to make money downtown or the northside for that matter. those areas are thick with big time developers, old money investors and the like. I invest solely on the far southside where there are far more opportunities and less competition. the neighborhoods can be a little rough but the money is there.

I agree, it’s a tight market downtown. Mine have also been on the south side. How far south are you? Do you live down there too?

I primarily invest in lower income areas like englewood, and roseland.

South Shore for me, and I actually live in my building (12 unit). Three streets over it’s really overcrowded (blocks with many 24 + unit buildings), but my street is mostly houses and two flats. Because of the lower density on my street there’s always parking and believe it or not it’s actually very peaceful. It’s 6:04 PM, my window is open and there’s not a sound from the street coming in aside from the occasional car passing by.

I didn’t initially intend to live here when I bought the building in 1998, but I have been since 2001. I’ve watched 6 flats in the area that were selling for $295,000 back in 1998 rise to $595,000 today. I could kick myself for my getting off track(6 years courting, marrying and divorcing a woman I wish I’d never met). I have to get the old prices out of my head and just look at the area for the way it is now. There’s still a lot of good things happening over here, but I don’t see another rise in appreciation like the rise since 1998. The rents just wouldn’t support it. Condo conversions are another story.

I’ve seen a few buildings for sale in South Shore that are overpriced with the justification being “great for condo conversion”. I would only think about looking into something for conversion if it were on a major street such as Jeffery, Yates or South Shore Drive. When I bought my building in 98, the seller had done a gut rehab with the idea of selling the units as condos. Individual furnaces, individual hot water tanks, breakfast counters, the works. After he was done he realized the area wasn’t ready for condos so far (5 streets over) from a major street so he decided to sell it instead. I was in the right place at the right time. Not so much skill, just luck.

I’d love to hear a bit about your experiences in Chicago with tennants and investing in general. Maybe we ‘Windy City’ dwellers can get a regional RE forum started here to swap war stories.

Take care,


Hey Howard! My name is Aaron. My experience in Real Estate Investing started with properties I purchased in Englewood as rental units. I later sold those properties and purchased rental units in the Roseland/Pullman area where I grew up. I also purchased a few others on the west side and a condo in South Commons, (which I regretibly sold going through a breakup.) In 2000 I purchased a three flat in Chatham which is my current residence. I just returned from South Shore. I spend a great deal of time there. My sister owns a house on Paxton, a lot of my daughters activities are at the South Shore Cultural Center, and I spend time on the lakefront as well. In 2001 I ran across a property on the westside. It was selling for 75k in a rough area where properties were worth up to 250k. It was here where my idea of Real Estate changed. I decided to try my first “flip”. I found a buyer with whom I would split the money on the table at closing, I found a Mortgage broker who worked with a “friendly” title company, and lastly a financier who would, for a fee, loan a down payment to my buyer and bring it to closing. Amazingly, the deal worked! There was about 84k at the table to split, of which almost half was all mine!Unfortunately, after that success my depression about my breakup led me to do almost nothing for a year and a half. I squandered my earnings and properties I had not sold had gone to foreclosure. I had since 1998, made all my money through real estate and it was gone. Fast forward to 2003. Coming out of my funk, I still had my home and my mental health, I took a temporary teachers position to support myself and my daughter of whom I had sole custody, with a will to return to what I loved doing most: Investing. In early 2004 I left teaching for good and started brokering deals again. I later started working short sales which I am currently doing. It has been a great and successful year with more to come.

Hello cayenne
I invest in south west suburbs of chicago, I do fsbo and rehabs. I just closed a deal today that was a rehab and I am walking away with 50k for six months not bad. I aslo will be doing another deal as fsbo for 3-4 months of holding which is a flip, walked away at purchase with 20k and will sell and make another 45k, I love this work!!!.
I would like to start meeting with other investors who have the same drive and risk as me and experience, so we can start helping others who need guidance and willing to start some type of chicago club and new realtionships.
I look foward to your response.

thank you

My Chicago investing has gone a little differently. My initial project was south west of Chicago. Bought a foreclosure home, rehabbed it, and sold it. Nice profit for only a few months work. My 2nd project was in the Woodlawn area, I bought a 6-flat hoping to renovate and sell. Fortunately for me, the market was so crazy, that someone came in and offered me $60k more than I paid for it 2 weeks after I closed. I took it. I’m always looking for a new project and I like the idea of starting up a Chicago REIC.

I would agree for a reic in chicago lets see how many people will reply.
peace in the windy city


To all chicago investors that would consider a group meeting for discussions for possible future investments, please reply and lets have fun.
I do look foward to meeting people that are serious and I am not a realestate broker or agent or mortgage broker. I am a true investor looking to make the almighty dollar just like everyone on this club, we dont have to dress formal lets be casual and be our own true self.
(time is money and money is time) so lets spend some good times together and make money. :slight_smile:

Hi All,

Let me start off by saying that I’m new to REI and have yet to do a first deal. I am however building up a REI jobber business (a.k.a. bird dogging) as a way to get my feet wet. I am very motivated in regards to learning all there is about REI and was looking to start networking with investros in the NW Indiana/Chicagoland Region. I’d love to link up a regional investment club where all of the seperate REIA’s can congregate together. It has been an idea I’ve been brainstorming on for a while but haven’t taken any action on as of yet.

Are any of you interested in investing in NW Indiana? I live in NW Indiana but commute to my jobs by car… both being in the south subs of chicago. Some of the south sub areas I drive through are the south side of Chicago, Calumet Park, Blue Island, Calumet City, Lansing, Glenwood, Lynwood, Flossmore, Chicago Heights & Crete. I’m even familiar with burb’s as far south west as Franfort. I haven’t even mentioned the NW Indiana communities I’m familiar with.

So for any of you who are interested in networking with me, feel free to contact me. I’d love to get together with any/all of you who are interested.


Hi! I am a rei. This has solely been my business since 1998. I have been involved in many types of investor deals. I would love to talk with you about getting involved in investing. feel free to contact me anytime.

i’m interested in the REIC concept - let’s keep this list growing.

I have started a Yahoo group for us to discuss setting up an REI club in Chicago.

It’s called ChicagoREIGroup and you can sign up at:

I’m your first member ;D

Gurnee was the place to be the last 20 years!! Seems like the growth is dieing off a little, but I moved 9 years ago so not sure the current status :stuck_out_tongue:

Time: 6:30pm – 9:30pm.

Registration time begins at: 6:00pm
Cover Charge: $10.00 if you RSVP, and $12 at the door if you don’t RSVP. You must RSVP by phone or email by Sunday at 10pm to receive the discount rate. We will send you a Reservation ticket via email or fax - please remember to bring it with you to the meeting for confirmation.

Event Location: St. Michael’s Church
Address: 1711 N. Cleveland Ave
City/State/Zip: Chicago, IL 60614
Parking Info/Details: There is plenty of free parking! (in the church lot in front of the entrance)

Thank you. I look forward to seeing you there!


Phil ~

Phillip Herrejon
The Chicago R.E.I. Club - Founding Director

Redhead Development LLC - Manager
Little Red Rehabber - Owner

312.375.7132 and

This is a great club! Call phil or e-mail phil to get on the list! He can also be contacted via

great . . . what day?

Every second Tuesday from 6:30-9:30! See you there! (It should be July 12th) this month.