Looking for off market investment properties in Chicago, Illinois? We rounded up 6 verified wholesale deals currently live on Offa, all priced under $500K. Each one comes with real photos, ARV estimates, and a direct line to the seller — once you sign up.
Photo by alex starnes on Unsplash
Last updated May 21, 2026. Inventory refreshes weekly.
6 Off Market Properties in Chicago, IL
These properties are sourced from verified wholesalers and updated weekly. Click any listing to see the full address, ARV breakdown, additional photos, and to contact the seller directly on Offa.
Why Invest in Chicago?
Chicago's combination of affordable entry prices and strong rental demand keeps it on every serious investor's shortlist. Off market is where the best deals live — current Offa inventory shows a median price near $299K with an average ARV spread of 69%. That's the kind of math that makes Chicago work for both flippers and buy-and-hold operators.
How to Buy Off Market in Chicago
Off market deals close fast — most go from offer to closing in 2-4 weeks. Here's the playbook:
- Browse Offa — see live deals in Chicago with photos, pricing, and ARV estimates.
- Run your numbers — apply the 70% rule, factor in rehab and holding costs, confirm comps.
- Contact the seller directly — every Offa listing has direct seller contact, no agents in the middle.
- Line up financing — Offa's lending partners offer up to 100% financing on qualified deals.
- Close in weeks, not months — wholesalers want speed. So do you.
Frequently Asked Questions
How do I find off market properties in Chicago, IL?
The fastest way is to use a marketplace built for off market deals. Offa aggregates listings from verified wholesalers across Chicago and the rest of Illinois, with real photos, pricing, and ARV estimates. Other approaches include joining local REI groups, building wholesaler relationships, and running direct mail campaigns to motivated sellers.
What's the average price of an off market property in Chicago?
On Offa, the median asking price for off market deals in Chicago is around $299K. Off market properties typically trade 69% below comparable retail listings, which is the equity spread investors target.
Are wholesale properties in Chicago a good investment?
Yes — when the numbers work. The Chicago market currently shows an average ARV spread of 69%, meaning the After Repair Value runs that much higher than the asking price on a typical deal. That's the equity cushion you have for renovation costs, holding expenses, and profit. Always run your own comps and rehab estimates before committing.
How fast do off market deals in Chicago sell?
Off market deals move quickly — most close in 2-4 weeks. Wholesalers want speed and certainty, and investors who can move fast win the best deals. Sign up free on Offa to get notified when new Chicago inventory hits.
The deals above are a snapshot — by next week, some will be under contract. Offa updates daily, and a free account unlocks the full address, ARV math, and direct seller contact for every listing.
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