Chris Aiello Law

๐Ÿ“ Villa Park, IL ยท Serving DuPage & Cook County

Real Estate Law · DuPage County, Illinois

Defer Capital Gains. Reinvest the Full Proceeds.

Residential and commercial closings handled with care from contract to keys, so the details are covered before you sign.

0Years of counsel
0Practice areas
1990Established

A properly structured 1031 exchange lets you sell investment property and reinvest the full proceeds into new property, deferring the capital-gains tax instead of handing a chunk to the IRS. Done wrong, the whole deferral collapses and the tax comes due. We structure and document 1031 exchanges for investors across DuPage and Cook County so the deferral holds up.

We have handled like-kind exchanges for Illinois investors for more than thirty years, as part of a full real estate practice. We coordinate with your qualified intermediary, your accountant, and the closings on both sides, so the exchange is documented correctly from the first contract to the final deed.

What We Cover

Topics in This Practice

We address the full range of issues in this area.

1031 exchange requirements (like-kind, t

The core rules that make a deferral stick: like-kind property, proper titling, and the reinvestment thresholds the IRS expects you to meet.

Qualified intermediary selection and coo

Coordinating the qualified intermediary who must hold the proceeds, because touching the money yourself blows the exchange.

45-day identification and 180-day exchan

The two hard deadlines that govern every exchange, 45 days to identify and 180 to close, and the documentation that proves you met them.

Delayed, simultaneous, and reverse excha

Structuring forward, simultaneous, and reverse exchanges depending on whether you are selling or buying first.

Boot calculation and partial deferral

Figuring out when cash or debt relief creates taxable boot, and how to structure the deal to minimize or plan for it.

Multi-property and portfolio exchanges

Exchanges that involve multiple relinquished or replacement properties, where the identification rules get more complex.
What to Expect

How a 1031 Exchange Comes Together

A 1031 exchange is a sequence of strict steps, and the order matters as much as the math. Before you sell, we make sure the relinquished property qualifies, the contract carries the right exchange language, and a qualified intermediary is in place to hold the proceeds, because if the cash touches your hands, the deferral is gone. Setting this up early is the difference between a clean exchange and a taxable sale.

Once the sale closes, the clock starts: 45 days to identify replacement property and 180 days to close on it. We track those deadlines, paper the identification correctly, and coordinate the replacement closing so nothing slips. We also flag boot, cash or debt relief that can create a partial tax, before it surprises you, and we work alongside your accountant so the legal and tax sides line up.

Why Hire Us

What Sets Our Work Apart

Local court experience

30+ years in DuPage and Cook County courts and recorder offices.

Direct attorney access

Chris or John handles your file personally.

Integrated with broader practice

Real estate, litigation, and estate planning under one roof.

Honest case assessment

We’ll tell you realistic outcomes, including when settlement is better than litigation.

Transparent pricing

Flat fees where possible, clear hourly rates where flat doesn’t fit.

Responsive communication

Your calls returned, your questions answered.

Service Area

Serving DuPage & Cook County

From our Villa Park office, we represent clients across DuPage County and the western suburbs of Chicago.

Villa ParkElmhurstLombardWheatonOak BrookDowners GroveAddisonOak ParkGlen EllynBloomingdaleHinsdaleWestmontDuPage CountyCook County
1031 Exchanges FAQ

Common Questions

Exchanges of real property held for investment or productive use in a trade or business. Personal residences don’t qualify. The replacement property must be ‘like-kind’ to the relinquished property, but ‘like-kind’ for real estate is very broad (apartment for farmland, retail for office, etc.).

You must identify potential replacement property within 45 days of selling the original property, and close on the replacement within 180 days. These deadlines are strict, IRS won’t extend them.

Yes, for a delayed exchange, you cannot touch the proceeds from the original sale. They must be held by a qualified intermediary (QI). We coordinate with QIs but don’t act as QI ourselves (legal conflict).

Yes, you can identify up to three replacement properties without limitation, or more under the ‘200% rule’ or ‘95% rule.’ This flexibility is one of the most powerful aspects of 1031 planning.

When you acquire the replacement property before selling the original. More complex and expensive, but useful when timing forces you to buy first. Requires careful structuring through an Exchange Accommodation Titleholder.

The exchange generally fails and the gain becomes taxable, with very few exceptions. These deadlines are firm and run from the sale closing, including weekends and holidays. That is exactly why we calendar them, paper the identification carefully, and stay on top of the replacement closing.

Usually no. The exchange has to be set up before you close on the sale, with a qualified intermediary in place to receive the funds. Once you have taken the proceeds, the opportunity is generally lost, so the time to call us is before the sale, not after.

Question About 1031 Exchanges?

A free consultation tells you whether you have a viable matter and what the realistic process looks like.