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Divorced More Than Once? Here’s How to Handle Maintenance in Illinois

By Nottage and Ward on July 14, 2025

If you’ve been through more than one divorce, understanding your rights and responsibilities under Illinois maintenance law is critical for your financial well-being.

Whether you’re paying or receiving support, knowing how remarriage, cohabitation, and modifications work can help you avoid unnecessary legal exposure and financial stress.

At Nottage and Ward, LLP, we regularly guide professionals, business owners, and high-net-worth individuals through complex divorce and support matters. If you’re managing spousal support from multiple divorces in Illinois, here’s what you need to know—and how to protect your financial future.

Understanding Spousal Support After More Than One Divorce in Illinois

In Illinois, spousal support—known legally as maintenance—is not automatic. The court evaluates various factors to determine if support is appropriate, how much should be paid, and for how long. But what happens if you’ve been married and divorced more than once?

Could You Have to Pay Maintenance to More Than One Ex?

Yes. Illinois courts can require a person to pay maintenance to more than one former spouse, provided each marriage resulted in a valid support order. Each case is considered based on its own facts, but courts will also review your ability to pay when multiple obligations are involved.

For example, if you’re already paying support from a first divorce and are now divorcing again, the judge may consider your existing obligation when deciding a new award, but they’re not prohibited from ordering additional support.

How Illinois Courts Evaluate Support in Multiple Divorce Situations

When deciding on spousal support, courts follow guidelines outlined in the Illinois Marriage and Dissolution of Marriage Act (IMDMA). Judges examine factors such as:

• Each spouse’s income and property
• The duration of each marriage
• The standard of living during each marriage
• Future earning potential and age
• The impact of prior support orders on current financial capacity

Under Illinois maintenance law, the court does have the discretion to deviate from standard formulas if a party is already meeting substantial obligations elsewhere, such as supporting a former spouse or children from a prior marriage.

This can result in reduced payments, temporary support, or structured agreements, particularly in high-net-worth divorce cases where more creative solutions are possible.

The Impact of Remarriage and Cohabitation on Maintenance

Remarriage has a direct and often immediate effect on spousal support. Under Illinois law:

• If the recipient of maintenance remarries, support from a previous spouse typically ends automatically on the date of the new marriage.
• If the payor remarries, there is no automatic change in obligations, but the new financial responsibilities may justify a motion to modify an existing support order.

What about cohabitation? This issue is more nuanced.

Spousal Support and Cohabitation

Illinois courts may terminate or reduce support if the recipient begins living with a new partner in a marriage-like relationship. However, this requires more than just sharing an address.

Courts look for signs of a committed relationship:

• Shared finances or joint purchases
• A long-term, stable arrangement
• Living together consistently
• Social presentation as a couple

If you suspect your former spouse is cohabiting, or if your financial situation has changed due to cohabitation with a new partner, an attorney can help determine whether a motion to terminate or reduce support is appropriate.

Modifying Maintenance Payments After a Second (or Third) Divorce

Spousal support is not necessarily set in stone. You can file a petition to modify alimony after subsequent divorce if there is a substantial change in circumstances. This may include:

• Job loss or significant reduction in income
• A new obligation to support another former spouse
• Retirement
• Serious illness or disability
• Remarriage or cohabitation of the recipient

High-income earners, in particular, may have options to structure lump-sum settlements, fixed-duration maintenance, or reviewable support orders that provide more control and predictability over time. When structured correctly, these solutions can avoid long-term legal entanglements and reduce financial risk.

Special Considerations for High-Net-Worth Divorce in Illinois

Affluent individuals going through multiple divorces face unique challenges and opportunities.

Negotiating Creative Settlements

In high-net-worth cases, courts may allow deviations from statutory guidelines if both parties agree. This can include:

• Buyouts of future support
• Structured payments over time
• Property transfers in lieu of maintenance
• Non-modifiable support agreements

Such options can protect wealth, reduce litigation, and provide a clean break when handled with proper legal guidance.

Prenuptial Agreements

If you’ve been divorced more than once and are considering marriage again, a well-drafted prenuptial agreement can prevent future maintenance claims. Illinois courts generally uphold prenuptial agreements, especially when negotiated transparently and with legal counsel for both parties.

Income from Trusts, Business Interests, or Investments

For professionals and business owners, support calculations may include income from partnerships, trusts, or investments. Multiple divorces can trigger deeper forensic evaluations of your financials. We work with experts to ensure an accurate representation of income and fair outcomes in these complex settings.

Tips for Protecting Your Financial Future

1. Keep Thorough Records: Track all payments, agreements, and communications related to support. This helps if disputes or modification requests arise later.
2. Avoid Informal Agreements: Verbal or off-the-books arrangements can lead to legal trouble. Always document changes to support a court-approved order.
3. Reevaluate After Life Changes: If your income drops or your ex remarries, don’t wait to seek a modification. Delays can cost you money you didn’t have to pay.
4. Work With a Lawyer Who Understands Complex Support Cases: With multiple divorces and higher incomes, your case may not fit the standard mold. Tailored advice can prevent costly mistakes and protect your assets.

Speak With a High-Net-Worth Divorce Attorney in Chicago

At Nottage and Ward, LLP, we focus exclusively on family law and have built our reputation for helping high-earning clients navigate complex support situations with confidence. We are listed by Martindale-Hubbell in its Bar Register of Pre-eminent Lawyers.

Whether you’re paying or receiving maintenance, managing obligations from more than one divorce, or facing a major change in your financial picture, we’re here to advocate for your best outcome.

We provide strong, strategic support rooted in decades of knowledge and an understanding of the challenges facing professionals, business owners, and other high-net-worth individuals. Give our Chicago divorce lawyers a call at (312) 332-2915 to learn more today.