How to Wholesale Real Estate in Chicago, Illinois (Step-by-Step Guide)

Wholesaling is a simple, low-risk way to break into real estate. In this guide, you’ll learn exactly how to wholesale real estate in Chicago—from finding motivated sellers to matching deals with real cash buyers—using clear steps and straightforward paperwork.

We’ll keep it practical and actionable. You’ll soon learn how to wholesale houses in Chicago with a repeatable process: build a buyers list, run basic comps to set ARV/MAO, choose between an assignment of contract or a double close, and move confidently to the finish line with an attorney-led closing.

• Is Wholesaling Real Estate Legal in Chicago?
• Chicago Real Estate Market Overview
• How to Wholesale Real Estate in Chicago (Step-by-Step)
• Pros & Cons of Wholesaling Houses in Chicago
• Chicago Resources: Title/Attorney Teams, REI Groups & Tools
• Free Download: The Ultimate Quick-Start Guide
• FAQs: Wholesaling in Chicago
• Final Thoughts on Wholesaling Houses in Chicago

---

---

---

Is Wholesaling Real Estate Legal in Chicago?

In Chicago, wholesaling is permitted when you transfer or sell your position in a signed purchase agreement (your equitable stake), so long as you comply with the Illinois Real Estate License Act. On the ground, that means you advertise the agreement (not the real estate itself), keep everything in written, assignable paperwork, and route funds and documents through attorneys and title at closing.

Illinois recognizes that your right to buy a property under a contract is personal property. You can transfer (assign) that right for a fee, so long as you aren’t acting as a broker for others without a license. The Illinois Real Estate License Act draws the line: routine activity that appears to represent others for compensation requires a license, while selling one's own contract does not. Unlicensed wholesalers may complete one assignment per year; beyond that, obtain a broker’s license through IDFPR.

Illinois is also an attorney-closing state. Buyers and sellers each have counsel; attorneys draft or review contracts and riders, hold earnest money in escrow, coordinate title, prepare the closing statement, and disburse funds. For wholesalers, that means your assignment fee—or both legs of a double close—is documented and paid through attorney/title escrow on the settlement statement, keeping the process transparent and compliant.

How this impacts wholesaling in Chicago:

• Use attorney-drafted paperwork: have a lawyer review your purchase and sale agreement and the assignment of contract (or double-close documents).
• Keep roles clear: you’re selling your contract rights, not negotiating as someone’s agent. Let attorneys handle legal language and back-and-forth.
• Route money through escrow: earnest money deposits and your assignment fee should flow through attorney/title escrow and appear on the HUD/CD.
• Coordinate early: send the PSA and assignment to both attorneys as soon as they’re signed so title, payoffs, city transfer stamps, and scheduling don’t slow you down.
• Plan timing for double closes: your attorney will line up wire cut-offs, two HUDs/CDs, and any transactional funding so both A→B and B→C record smoothly.

If you’re learning how to wholesale real estate in Chicago, these are the three compliant structures you’ll use most often—each fits different privacy, capital, and disclosure needs. We’ll refer back to them as we price deals with ARV/MAO, build a buyers list, and coordinate funding.

Read Also: Is Wholesaling Real Estate Legal In Illinois? 

 

If you limit your activities to selling your own contract rights, use clear, written documents, and avoid representing others without a license, you can wholesale confidently in Chicago. For more volume, pursue an Illinois broker’s license and continue to route funds and documents through attorneys and title.

Educational only — consult an Illinois real estate attorney and review the Real Estate License Act for deal-specific guidance.

---

---

Chicago Real Estate Market Overview

Chicago rewards wholesalers with speed and repeatability. The metro’s size and job base keep demand steady, while its vintage housing stock—the bungalow belt, classic greystones, worker cottages, and two-to-four flats—consistently benefits from thoughtful updates. If you’re learning how to wholesale real estate in Chicago, look for affordable-to-mid-price pockets where light or moderate renovations, small layout fixes, and routine title cleanup can turn into quick, clean assignments.

Success here is hyper-local. In a gridded city, values can shift within a few addresses based on the nearest “L” or Metra stop, school catchments, parking, and unit mix. The operators who win keep comps tight, ARV credible, and MAO disciplined. If you’re figuring out how to wholesale houses in Chicago, start with fee-simple 1–4 unit homes and straightforward two- to four-flats; branch into mixed-use or larger multis only after you’ve dialed in finish levels and rental assumptions for your target blocks.

What to watch in Chicago:

• Days on market & absorption: Faster resale near your ARV = stronger end-buyer demand.
• Inventory by side/neighborhood: Low months of supply favors quick assignments; rising supply demands tighter pricing.
• Cash activity in comps: “Cash” notes & no-financing terms signal real investor depth.
• Discount to ARV: Back into MAO from your buyer’s margin (flip vs. rental) and your target fee.
• Rental reality: BRRRR method buyers care about rent comps, unit mix, and realistic operating costs.
• Public-record flags: liens, violations, permit history, and tax delinquencies can indicate motivation—price the cure.
• Property type friction: two- to four-flats are beginner-friendly; larger or mixed-use assets add underwriting steps.

Fold these indicators into every underwriting pass, and your buyer packets become “yes/no in minutes.” To kick things off, here are Chicago submarkets where wholesalers consistently gain momentum:

 

 

 Read Also: How To Wholesale Real Estate In Illinois

How to Wholesale Real Estate in Chicago (Step-by-Step)

Ready to turn potential into profit? Here’s your hands-on roadmap for how to wholesale real estate in Chicago. We’ll walk you from that first seller conversation through to attorney-led closing—building a true cash buyers list, running tight comps, setting credible ARV and MAO, and choosing between an Illinois‑compliant assignment or double close. Treat the nine steps below as your weekly checklist. Click any step to jump straight to what you need:

1. Partner with a Wholesale Mentor
2. Learn Chicago Wholesaling Laws & Contracts
3. Analyze the Chicago Market (Comps, ARV, MAO)
4. Build a Cash Buyers List in Chicago
5. Find Motivated Sellers & Distressed Properties
6. Put Properties Under Contract
7. Assign Contracts to Cash Buyers
8. Close Deals & Collect Your Assignment Fee
9. Double Close When Necessary

Partner with a Wholesale Mentor

Chicago’s neighborhoods and ordinances can be overwhelming to newcomers. Working with someone who has already closed assignments and double closes under Illinois law will shortcut the trial-and-error stage. The right mentor can help you avoid missteps (like misunderstanding the Illinois Real Estate License Act, mispricing ARV, or using non‑assignable contracts) and ensure you focus on the tasks that actually lead to executed contracts and paid fees.

 

 

How to choose the right mentor (quick checklist):

• Recent local wins: confirm they’ve closed Chicago assignments or double closes in the last year.
• Documented process: they can clearly explain comps, ARV, MAO, offers, and disposition steps.
• Buyer network: they introduce you to buyers with proof of funds.
• Compliance-minded: they understand marketing the contract, escrow rules, and the one‑deal‑per‑year limit for unlicensed wholesalers.
• Availability: scheduled office hours, call reviews, and weekly targets—not just a course portal.
• Communication style: straightforward feedback and clear expectations.

Where to find a mentor in Chicago (proven channels):

• Neighborhood investor meetups & flip tours—bring a one-page deal kit sample to spark conversations.
• Referrals from investor-friendly attorneys, hard-money lenders, and brokers who see who’s closing.
• Online communities (local REI forums)—look for members sharing redacted HUDs/CDs and specific buy boxes.
• Cook County auction observation and rehabs open houses—introduce yourself to the people bidding or renovating.
• Targeted outreach—identify three closers in your target ZIPs, pay for a ride‑along or quick deal critique, and offer value in return (buyers, leads, comp analysis).

Tip: When you're learning how to wholesale houses in Chicago, set weekly metrics—new sellers contacted, offers sent, buyers added, contracts reviewed. Activity compounds faster than chasing perfection.

Need a Mentor? Start Here (Free PDF)

If you’ve been thinking, “I just need someone to show me the moves,” we’re here. Grab our free, step-by-step PDF that shows you how to wholesale in any state (including Illinois)—from legal basics to buyer lists, offers, and closing. It’s concise, actionable, and designed for your first deal. Download the free guide now:

Read Also: How To Invest In Real Estate In Illinois

Learn Chicago Wholesaling Laws & Contracts

Before pounding the phones, lock down the paperwork and rules that keep you legal. Under Illinois law, your task is to sell your contractual interest—not broker the property for someone else. That distinction lets assignments and double closes work in an attorney-led environment.

 

 

 

In practice, here’s how that plays out when you’re learning how to wholesale houses in Chicago: use an assignable PSA approved by an attorney, clearly state that you may assign, market your contract to verified buyers, and have counsel escrow the EMD and show your fee on the settlement statement. If the seller doesn’t allow assignment or your spread is large, choose a double close and let counsel handle two HUDs/CDs and wire logistics.

Educational only—consult an Illinois real estate attorney for deal‑specific guidance. Useful Chicago diligence sources: Cook County Recorder (deeds/liens), Assessor (taxes), the City’s permit/violation portals, and the Chicago Zoning Map.

Analyze the Chicago Market (Comps, ARV, MAO)

A cheap lead is worthless without a reliable price. If you’re mapping out how to wholesale real estate in Chicago, start by analyzing the Chicago market with a tight underwriting routine: pull block-level comps, set a realistic ARV, estimate repairs with a line-item scope, back into MAO from your buyer’s margin, and package a deal kit attorneys can close quickly. This approach works across the bungalow belts, greystone corridors, and all 77 community areas.

1. Define the subject: beds/baths, year built, above‑grade square footage, lot size, parking, legal use (check zoning and Certificate of Zoning Compliance), tenant status, and obvious capex items (roof, mechanicals, foundation, porch).
2. Pull comparables (last 3–6 months): same side/neighborhood, ≤0.5–1.0 miles, similar style/size (±15%), and similar condition. Separate renovated vs. dated inventory; for 2–4 flats compare to other small multis.
3. Filter & adjust: remove outliers (estate sales with unusual concessions). Adjust for square footage, bed/bath count, garage/parking, corner lots, and renovation level. Note “cash” or “as-is” comps—those are your buyer base.
4. Set ARV (After-Repair Value): take the median of your top three renovated comps or apply price‑per‑square‑foot from those comps to your subject fully updated.
5. Estimate repairs: start with a per‑foot range (light/moderate/heavy) then refine by line item (kitchen, baths, mechanicals, roof, windows, exterior, code items). Add a 10–15% contingency.
6. Know your buyer’s target: flippers often underwrite ≈ ARV × 70–75% − repairs − soft/hold; buy-and-hold buyers care about DSCR/rent comps. Ask your buyers for their specific “buy box.”
7. Compute MAO Formula (Maximum Allowable Offer): MAO = Buyer Target − Your Assignment Fee − Buyer closing/holding. This protects your spread and still leaves room for the end buyer.
8. Pressure-test: check days on market near your ARV, verify rent comps (if BRRRR exit), confirm liens/violations with Cook County and the City’s Permit Portal, and gauge extra costs like City water clearance and transfer stamps.

Chicago comping tips: Co-ops are rare, but condos can carry high assessments; most beginners stick to fee-simple 1–4 unit properties and small multis. Mastering these basics is central to how to wholesale houses in Chicago. Always verify legal unit count before assuming a garden apartment is legitimate, and remember that parking and proximity to an “L” stop can add (or subtract) value.

 

 

Illustrative numbers: ARV = $350,000 (from top three renovated comps). Repairs ≈ $45,000 (moderate). Buyer target (flip) ≈ $350,000 × 0.72 − $45,000 − $15,000 soft/hold = $191,000. Your fee goal = $10,000 → MAO ≈ $181,000. If the seller signs at $172,000, you’ve locked a spread while leaving profit for the buyer.

---

---

Build a Cash Buyers List in Chicago

Your buyers list turns signed contracts into assignment fees. To succeed at how to wholesale houses in Chicago, cultivate real cash buyers—people who can close without a mortgage contingency (personal cash, LLC funds, or hard money with no appraisal). A strong list shortens decision windows, reduces fallout, and lets you price offers with confidence because you know what local investors will pay in each neighborhood.

Use the quick table below as your field guide to Chicago cash‑buyer sources. It highlights signals that a buyer is real and the first question to ask to confirm proof of funds, buy box, and assignment‑friendly posture:

 

 

Vetting buyers (Chicago checklist):

• Proof of funds: Bank statement or credit line dated within 30 days, matching the purchasing entity.
• Entity & signer: LLC name, operating agreement, authorised signatory; W‑9 on file.
• Buy box: Side(s) of the city, max price, beds/baths, property type (1–4 unit, small multi, mixed-use), rehab appetite, exit (flip vs. rental).
• Closing speed: 10–21 days; confirm attorney/title preferences.
• Earnest money: Deposit ready to wire to attorney escrow; non‑refundable after inspection.
• Track record: Recent closing statements (redacted) or references from an attorney/lender/GC.
• Assignment-friendly? Confirm they buy assignments; otherwise earmark them for double‑close deals.

How to talk to cash buyers (quick hits):

• Lead with certainty: “Attorney escrow, clear timelines, and assignment fees shown on the HUD/CD.”
• Be specific: “2-flat in North Lawndale, 2,100 sf, moderate rehab; asking $230k; ARV $350k from three renovated comps.”
• Decision window: 24–48 hours with a small deposit; walk-through by appointment.
• Backups ready: Keep two or three buyers per neighbourhood; if the first declines, send it to the next.

Organise your list like a pro: Keep a CRM or spreadsheet with columns for name, entity, phone/email, buy box, POF date, attorney preference, deposit amount, and side/ZIP tags (Austin, Bronzeville, Garfield Park, Hermosa, Avondale, Englewood, South Shore). Tag each buyer by rehab level and exit strategy so you can quickly match deals.

---

*Want to learn the proven strategies for finding cash buyers? Check out our video below where Alex Martinez explains How To Find Cash Buyers For Wholesaling! [FREE]—the tips work in Chicago too.

---

Compliance reminder: market your contract (equitable interest), not the house; keep ads factual; route all funds through attorney escrow, and ensure your assignment fee appears on the settlement statement. Remember: unlicensed wholesalers may assign only one deal per 12 months in Illinois—get licensed if you plan to do more.

Find Motivated Sellers & Distressed Properties (Chicago)

Wholesale deals begin with motivation—owners who prize speed and certainty over top-dollar. If you’re learning how to wholesale real estate in Chicago, focus on the seller profiles that show up again and again: absentee landlords tired of turnovers, heirs managing estates, owners behind on taxes or mortgages, and homeowners facing code violations or deferred maintenance. Solve their timing and convenience problems and you can secure discounted contracts your buyers will compete for—creating steady off-market deal flow.

Where to source motivated sellers: Combine direct outreach with public records. Keep your messaging honest and remember you’re marketing your contract, not acting as a broker:

How to contact motivated sellers:

• First touch: Mail a postcard or simple letter and follow up with a respectful call. Keep it straightforward: “We can close with your attorney, as‑is, on your timeline.”
• Follow‑up cadence (weeks 1–4): Call → text/voicemail → second letter → call again. Rotate channels and never spam. Log each touch.
• Conversation goals: Understand condition, timeline, occupancy, motivation, and price expectations. Ask for photos or schedule a walk‑through.
• Value proposition: Certainty, speed, minimal showings, attorney‑held escrow, fees on the HUD/CD.
• Qualification: Confirm the decision‑maker (all owners/heirs), attorney info, and any liens/violations that must be addressed.

How to tell if a seller is truly motivated:

• They prioritise timing and convenience over top price.
• They grant access for an inspection quickly and agree to realistic dates.
• They volunteer problems: code violations, tenant issues, tax arrears.
• They ask about closing logistics (attorney, escrow, payoffs) rather than marketing the house.

Organise follow‑ups like a pro: Use a CRM with fields for owner name, phone/email, address, PIN, occupancy (vacant/tenant/owner), condition notes, liens/violations, timeline, price feel, and next action date. Tag by source (probate, tax lien, code violation, driving for dollars, MLS “as-is”). If you’re mapping out how to wholesale houses in Chicago, remember that most deals land after the fifth to seventh touch—stay consistent.

Compliance reminders: Respect Do‑Not‑Call rules and opt-outs; get consent for texts; keep marketing honest; do not misrepresent your role. Route earnest money and your assignment fee through attorney/title and show them on the HUD/CD. If parties object to assignments or your spread is large, switch to a double close.

Dial in these sourcing and follow‑up skills and you’ll build a consistent pipeline of discounted contracts ready for your buyers. Combine this with disciplined comps, ARV, and MAO and you’ll package Chicago wholesale deals buyers can underwrite in minutes.

---

---

Put Properties Under Contract

This is the moment when interest becomes a binding agreement. If you’re mapping out how to wholesale real estate in Chicago, your aim is to price the deal correctly, present a simple offer, and sign an assignable purchase contract that attorneys can close smoothly. In Illinois’ attorney-driven process, that means tight numbers (ARV, repairs, MAO), clear terms, and funds routed through attorney escrow with your assignment fee shown on the HUD/CD.

Price it before you write it (ARV → Buyer Target → MAO)

1. ARV (After-Repair Value): Base it on the median of your top three renovated comps (or price‑per‑square‑foot times above‑grade area) in the same neighborhood.
2. Repairs: Estimate by scope (light/moderate/heavy), then refine line items (kitchen, baths, mechanicals, roof, windows, exterior, violations). Include a 10–15% contingency.
3. Buyer Target: Many flippers underwrite ≈ ARV × 70–75% − repairs − soft/hold costs; BRRRR buyers use rent/DSCR calculations. Know each buyer’s buy box.
4. MAO (Maximum Allowable Offer): MAO = Buyer Target − Your Assignment Fee. If the seller won’t accept MAO, adjust terms or consider a double close/novation.

 

Chicago offer & contract flow (step-by-step)

1. Identify all decision-makers & access: Confirm who can sign, any heirs, tenant status, and a short inspection window.
2. Present benefits first: Attorney-managed sale, as‑is condition, minimal showings, flexible closing.
3. State a clear price & timeline: Short closing (10–30 days), realistic inspection period, and EMD delivery date.
4. Send a clean, assignable PSA: Include assignment language or a rider; attach required disclosures (e.g., lead-based paint, radon, city transfer stamp obligations); allow reasonable access.
5. Open attorney/title escrow & wire EMD: Buyer and seller counsel coordinate; funds and documents flow through escrow.
6. Choose your path: Use a simple assignment when everyone is comfortable with your fee; choose a double close when privacy or assignment bans require it.

 

 

Negotiation playbook (friendly & firm)

• Lead with certainty: “Attorney escrow, as‑is purchase, your timeline.”
• Trade, don’t take: If price is firm, ask for more access or time; if time is tight, sweeten price slightly.
• Anchor a range: Start a bit below your MAO to leave room to agree quickly.
• Be transparent: Explain that you may assign or double close; clarity builds trust.
• Write while you talk: Send the PSA the same day a verbal “yes” happens.

Quick example: ARV = $350,000; Repairs = $45,000; Soft/Hold = $15,000. Buyer target at 72% ≈ $350,000 × 0.72 − $45,000 − $15,000 = $189,000. Your fee goal = $10,000 → MAO ≈ $179,000. If the seller signs at $170,000, you’ve created room for closing costs and still exceeded your fee target.

Document prep & hand‑offs: Have a one‑page deal kit ready: property facts, photos, three ARV comps, rehab scope, access notes, disclosure list, and known title/violation items (pull recorder and permit screenshots). This speeds attorney review and lets buyers underwrite quickly.

Compliance: Market your contract, not the property; keep ads factual; route all funds through attorneys/title; show your fee on the HUD/CD. When assignability is banned or the spread is sensitive, switch to a double close.

---

*For in-depth training on real estate investing, Real Estate Skills offers extensive courses to get you ready to make your first investment! Attend our FREE Webinar Training and gain insider knowledge, expert strategies, and essential skills to make the most of every real estate opportunity that comes your way!

---

Assign Contracts to Cash Buyers

You’ve secured an assignable purchase agreement—now you need the right investor at the right price. If you’re exploring how to wholesale houses in Chicago, your job is to make underwriting effortless: package a tight deal kit, set a decision window, verify proof of funds, and execute a clear, attorney-approved Assignment of Contract. Keep your messaging truthful—you’re selling your contract rights, not acting as a broker.

Package a “deal kit” buyers can underwrite fast

• Snapshot: Address, beds/baths, above‑grade square footage, lot size, zoning/Certificate of Zoning Compliance, tenant status.
• Photos & condition: Current interior/exterior photos; brief summary of what’s functional vs. what needs work.
• ARV comps: Top three renovated sales with distances and close dates; include price-per‑sf notes.
• Repair estimate: Light/moderate/heavy scope with line items and contingency.
• Numbers: Your assignment price, inspection/access instructions, and a decision deadline (24–72 hours).
• Docs status: Signed PSA (assignable), attorney contact info, and any known liens or code violations summarised.

 

 

What your Assignment of Contract should include

• Parties & property: Your entity (Assignor), buyer entity (Assignee), seller info, and the full address.
• PSA reference: Date of the original PSA and confirmation it’s assignable or that consent has been granted.
• Assignment consideration: Your assignment fee and the total price the assignee agrees to perform under the PSA.
• Deposits & timelines: Buyer deposit amount, decision/inspection window, and key dates tied to the PSA.
• Access & approvals: How/when the buyer can inspect; note any HOA or municipal approvals if applicable.
• Disclosures: As‑is condition, summary of known code violations, and a statement that the assignee accepts the PSA obligations.
• Attorney/title details: Name the escrow holder and note who holds originals (no need to discuss the next closing).

Outreach that gets fast responses

When assignment makes sense (and when it doesn’t)

• Use assignment when: The seller is comfortable with your fee, the PSA allows assignment, and your buyer’s buy box matches perfectly.
• Switch to a double close when: The PSA forbids assignment, your spread is sensitive, or an institutional buyer requires you to be in the chain of title.

Common pitfalls to avoid

• Blasting your entire list—always match deals to buyer criteria first.
• Burying the lead—put the assignment price, ARV comps, and decision deadline at the top of your email.
• Skipping POF or entity checks—verify before scheduling access.
• Using vague paperwork—have your attorney draft clear assignment language tied to the PSA.

Pro tip: If you’re focused on how to wholesale houses in Chicago, track every assignment in a simple spreadsheet (buyer, entity, POF date, neighbourhood/ZIP tags, decision window, deposit received, attorney contact). Keep two backup buyers per neighbourhood; if one says no, the next is ready.

---

---

Reminder: You’re selling your equitable interest in the contract. Keep communications honest, respect privacy, and coordinate through counsel. Save the closing details for the next stage.

Close Deals & Collect Your Assignment Fee

You’ve assigned the contract—now it’s the finish line. If you’re learning how to wholesale houses in Chicago, this stage is all execution: in Illinois’ attorney-led system, your assignment consideration appears as a line item on the settlement statement (ALTA/HUD/CD), and every dollar moves through attorney escrow. Keep both attorneys and title in sync, answer curative requests fast, and verify wire instructions so the deal records cleanly and your fee lands without surprises.

Chicago closing timeline (attorney-led)

 

 

How your assignment fee is collected in Chicago: It’s shown as a line item on the HUD/CD, paid from buyer funds at closing, and disbursed through attorney/title escrow. Provide a W‑9 or W‑8BEN so your attorney can report it correctly.

Chicago closing quirks to handle early

• Water & transfer stamps: Chicago requires a final water bill certification and city/county transfer stamps—start this process early.
• Tenancy & possession: Verify whether the property will be delivered vacant or occupied; rent‑controlled or subsidised units add complexity.
• Violations & permits: Cook County/City code issues can stall your closing. Provide known violations and open permits to counsel immediately.

Wire & fraud‑safety checklist

• Always confirm wiring instructions by phone directly with the attorney’s office.
• Send a voided check or bank letter by secure means; avoid public links.
• Request same‑day confirmation once your fee has been disbursed (reference number + amount).

Common snags (and how to avoid them)

• Deposit delays: Calendar your buyer’s EMD due date; if it’s late, alert your backup buyer list.
• Hidden liens/violations: Ask for a curative checklist from your attorney on day one; share contact info for payoff and code offices.
• Entity mismatches: Make sure your assignment, PSA, and HUD/CD have the exact same names and EINs.
• Missing tax clearances: Order water/transfer stamps early and verify city tax compliance.

 

Double Close When Necessary

Assignments are the simplest path for beginners, but some deals require a different approach. In Illinois, a double close (also called a back-to-back or simultaneous closing) involves buying the property from the seller (A→B) and immediately reselling it to your investor (B→C). This protects your spread from scrutiny, meets PSA requirements that forbid assignments, and keeps institutional buyers compliant with their guidelines.

 

When to use a double close in Chicago

• Spread privacy: When your margin is large or sensitive and you want to keep it off the buyer’s radar.
• No-assignment PSAs: When the purchase agreement forbids assignment and the seller’s counsel won’t consent.
• Institutional buyers: When REOs, hedge funds or auction houses require you to appear in the chain of title.
• Marketing flexibility: When you plan to wholetail (light cleanup) before resale or you want to list on the MLS.

 

 

Pros and trade‑offs of double closing

 

 

How to decide—assignment vs. double close

• Choose assignment when the PSA allows it, the seller and buyer accept your fee, and your spread is modest.
• Opt for a double close when the PSA forbids assignment, your fee is large, privacy matters, or institutional buyer rules require you in the chain of title.

Pros & Cons of Wholesaling Houses in Chicago

Every market has trade-offs. Below is a city-specific snapshot of why Chicago works for wholesalers—and what friction points to plan for as you scale.

 

 

Chicago rewards investors who do their homework, respect the legal framework, and build real relationships. Be clear about transfer taxes, rent‑control issues, and neighborhood trends, and you’ll stay a step ahead of the competition.

Chicago Resources: Title/Attorney Teams, REI Groups & Tools

Set yourself up for success by building a toolkit that fits Chicago’s market and regulatory environment. Use these resources to verify ownership, pull code violations, understand zoning, vet attorneys, and connect with buyers.

• Title & Attorney Teams (find and vet)
  • Illinois State Bar Association Directory — verify attorney status and find real estate specialists.
  • Cook County Bar Association — connect with local counsel experienced in assignments and double closes.
  • IL Department of Financial & Professional Regulation — check license status for attorneys and title agents.
• Ownership, Liens & Recording
  • Cook County Recorder of Deeds — deeds, mortgages, liens, and recorded documents.
  • Cook County Treasurer — tax bills and payment history.
  • Cook County Assessor — PIN lookups, property descriptions, and assessed values.
• Violations, Permits & Zoning
  • City of Chicago Department of Buildings — permits, Certificates of Occupancy, code violations.
  • Chicago Zoning Ordinance & Map — confirm legal uses and zoning overlays.
  • 311 Service Requests (Data Portal) — track complaints and violations on target properties.
• Courts & Distress Signals
  • Cook County Clerk of the Circuit Court — foreclosure & tax sale cases.
  • Cook County Probate Court — estate filings (useful for probate leads).
• Market Data, Comps & Rentals
  • MRED (via agent) — closed sales, actives, pendings.
  • Chicago Association of REALTORS® Market Stats — trends by community area.
  • Rentometer & Zillow Rent Index — rental comps for BRRRR underwriting.
• Networking & Buyers
  • Chicago REIA, Midwest REI Club, and local meetup groups — flip tours, masterminds, networking.
  • Facebook Groups (Chicago Real Estate Investors, West Suburban REI, North Side Flippers) — online buy box sharing.
  • BNI & local chambers — connect with attorneys, title agents, and contractors.
• Compliance & Consumer Protection
  • Illinois Real Estate License Act (225 ILCS 454) — defines broker activity and one-deal limit for unlicensed wholesalers.
  • IDFPR — oversees licensing, advertising rules, and consumer complaints.

Bookmark these resources and leverage them on every file. Access to accurate public data and a knowledgeable attorney/title team will save you countless hours and headaches, while the investor groups keep your buyer pipeline fresh.

Free Download: The Ultimate Guide to Getting Started in Real Estate

Ready to take action? Download our free, beginner-friendly quick-start guide, designed to help you begin your real estate journey. Whether you want to flip, wholesale, or build a rental portfolio, this step-by-step PDF will get you moving—no big budgets or experience required.

• Why real estate works for beginners: A practical path to wealth without needing huge capital or a license to start.
• Find deals without ad spend: Why the MLS is often the most reliable source for deals (and how to filter smarter).
• Rentals for long-term wealth: Turn today’s active income into passive cash flow and future appreciation.
• Wholesaling basics: Understand ARV, data-driven offers, and when to choose assignment vs. double close.

FAQs: Wholesaling in Chicago

We’ve gathered concise answers to the most common questions about how to wholesale real estate in Chicago. Each answer is short and direct to help you move from research to action.

Is wholesaling real estate legal in Chicago?

Yes—if you sell your contract rights (not the property) and follow Illinois licensing rules. Unlicensed wholesalers may assign only one contract per 12 months; otherwise, you need a broker’s license.

Do I need a license to wholesale houses in Chicago?

No license is required to assign your own contract once per year. If you intend to do more than one assignment within 12 months, you must obtain an Illinois broker’s license.

How long does a wholesale deal take in Chicago?

Most attorney-led closings take 10–30 days, though code violations, tenant issues, transfer stamps, or water certifications can add time.

Can I wholesale MLS properties in Chicago?

Yes—if your purchase contract is assignable and your role is disclosed. If the seller or institution forbids assignment or your fee is large, choose a double close.

How do I start wholesaling with little money in Chicago?

Build a cash buyers list, learn comps/ARV/MAO, source on- and off-market leads, and use modest earnest money deposits; get licensed if you plan multiple deals.

Can I wholesale tenant-occupied properties in Chicago?

Yes, but buyers will underwrite based on leases and Chicago’s tenant ordinances. Disclose occupancy status and rental terms early.

What is an assignment of contract?

It transfers your rights in a signed purchase agreement to another buyer for a fee. Attorneys prepare the document, and escrow disburses your fee on the HUD/CD.

When should I double close instead of assign?

Use a double close for larger spreads, “no assignment” clauses, or when institutional buyers require you to appear in the chain of title.

Does the seller see my assignment fee in Chicago?

On assignments, your fee is a line item on the settlement statement. In a double close, your spread is private because the fee is embedded in the B→C leg.

Final Thoughts on Wholesaling Houses in Chicago

Chicago rewards investors who combine local knowledge with disciplined execution. If you’re serious about learning how to wholesale real estate in Chicago, follow this playbook: choose a handful of neighborhoods, pull tight comps, consult an Illinois attorney, and meet real cash buyers. Lock a clean contract, choose between assignment or double close, and move quickly. Start small, learn each block, and scale thoughtfully—this is how to wholesale houses in Chicago confidently, legally, and profitably.

---

---

*Disclosure: Real Estate Skills is not a law firm, and the information contained here does not constitute legal advice. You should consult with an attorney before making any legal conclusions. The information presented here is educational in nature. All investments involve risks, and the past performance of an investment, industry, sector, and/or market does not guarantee future returns or results. Investors are responsible for any investment decision they make. Such decisions should be based on an evaluation of their financial situation, investment objectives, risk tolerance, and liquidity needs.