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What Should You Do If You Get Multiple Offers as a Seller in Chicago?

A Downtown Chicago real estate expert explains how to choose the strongest offer, not just the highest price.
Christine Hancock  |  January 29, 2026

What Should You Do If You Get Multiple Offers as a Seller?

Getting multiple offers is exciting—but how you handle them can significantly impact your final outcome. The goal isn’t just to pick the highest number; it’s to choose the strongest overall offer.

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Step 1: Slow the Process Down (Briefly)

Your first move should not be accepting anything immediately. Even in a competitive Downtown Chicago market, pausing allows your agent to:

  • Fully compare price and terms

  • Identify red flags (financing, contingencies, timelines)

  • Signal to buyers that competition is real

A short window creates leverage without risking momentum.

Step 2: Compare More Than Just Price

In multiple-offer situations, smart sellers weigh the entire offer package, including:

  • Financing type (cash vs. conventional vs. FHA/VA)

  • Down payment strength

  • Appraisal gap coverage

  • Inspection contingencies (or lack thereof)

  • Buyer flexibility on closing or possession

In condo-heavy Downtown Chicago markets, financing strength and appraisal risk often matter more than an extra few thousand dollars.

Step 3: Use “Highest & Best” Strategically

Requesting “highest and best” offers works best when:

  • You already have 2–3 strong offers

  • Buyers are emotionally invested

  • Your home is clearly in demand

This step often increases price and improves terms—but it should be used intentionally, not automatically.

Step 4: Consider a Counteroffer (or Multiple Counters)

You’re allowed to counter one offer—or even more than one—depending on strategy. Sellers often counter to:

  • Shorten inspection periods

  • Increase earnest money

  • Clarify appraisal protections

  • Adjust closing timelines

This is where experienced negotiation makes a measurable difference.

Step 5: Choose Certainty, Not Just Excitement

The “best” offer is usually the one most likely to close cleanly and on time. Sellers sometimes regret choosing:

  • The highest price with weak financing

  • An aggressive buyer who later renegotiates

  • An offer with vague or risky contingencies

Certainty is leverage—especially in Downtown Chicago condos where deals can fall apart late.

Step 6: Have a Backup Offer in Writing

If you receive multiple strong offers, always secure a backup offer. If the first deal fails, you often:

  • Avoid going back to market

  • Maintain negotiating power

  • Shorten total days on market

Backup offers are an underused advantage for sellers.

 

Why Seller Representation Matters Most in Multiple-Offer Situations

Multiple offers create opportunity—but also complexity. The right strategy can net you:

  • A higher effective sales price

  • Fewer post-inspection surprises

  • A smoother closing

How offers are handled often matters more than how many you receive.

 

Quick Seller Decision Matrix: How to Compare Multiple Offers

Offer Factor Offer A Offer B Offer C Why It Matters to You
Purchase Price $ $ $ Higher isn’t always better if risk increases
Financing Type Cash / Conv / FHA     Cash & conventional typically close smoother
Down Payment % % % Higher = stronger buyer commitment
Appraisal Gap Coverage Yes / No / $     Protects you if appraisal comes in low
Inspection Contingency Waived / Limited / Full     Fewer contingencies = less renegotiation
Earnest Money $ $ $ Indicates buyer seriousness
Closing Timeline Days Days Days Aligns with your next move
Possession Flexibility Yes / No     Helpful if you need post-closing occupancy
HOA Experience Strong / Moderate / Weak     Condo deals fall apart over HOA issues
Overall Risk Level Low / Med / High     The offer most likely to close often wins

How Sellers Should Use This Table

  • Fill it out side by side with your agent

  • Circle the offer with the best balance of price + certainty

  • Don’t overvalue small price differences if risk jumps significantly

  • Use it to guide counteroffers or “highest & best” requests

In Downtown Chicago, the strongest offer is usually the one that closes cleanly, appraises, and survives inspection—not just the one with the biggest headline number.

If you’re preparing to sell in Downtown Chicago or the West Loop, the way your offers are handled can change your final outcome.

Let’s talk about a strategy that protects your price and your timeline.

Pro Tip: Is the agent who suggest the highest list price, the best agent?

 

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