One of the biggest decisions Chicago homeowners face is whether to sell their current home first or buy their next home first. Both options have advantages and risks, and the right choice depends on your financial position, the type of home you are selling, the neighborhood you are targeting, and current market conditions.
In areas like Logan Square, Lincoln Park, Bucktown, Wicker Park, and Andersonville, timing and competition can vary by season, property type, and price point. This guide will help you understand your options and make the best decision for your situation.
The Key Question: Do You Want Certainty or Flexibility?
Every move involves two major steps
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Selling your current home
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Buying your next home
The question is which step should happen first. Your answer comes down to what matters more to you: financial certainty or housing flexibility.
Below are the advantages and disadvantages of both approaches.
Option 1: Sell First
Selling first is the most common strategy because it gives you clarity about your financial position before you buy your next home.
Benefits of Selling First
1. You know exactly how much you will net
Once your home sells, you will have a clear understanding of:
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Your net proceeds
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Your buying budget
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Your down payment
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Your financing requirements
This eliminates guesswork and helps you make stronger offers.
2. You reduce financial stress
You avoid carrying two mortgages at the same time, which reduces risk and simplifies your move.
3. You can negotiate from a position of strength
Buyers tend to move quickly in desirable Chicago neighborhoods. If your home is well priced, you may secure a fast offer and favorable terms, which creates momentum for your next purchase.
4. You avoid being rushed to sell
If you buy first, you may feel pressured to sell quickly to avoid overlapping housing expenses. Selling first keeps the timeline in your control.
Challenges of Selling First
1. You may need temporary housing
If you cannot find your next home immediately, you may need to:
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Stay with family
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Use a rental
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Secure a short term lease
This adds an extra step but is often worth the tradeoff.
2. Fast moving markets can increase pressure
In competitive neighborhoods like Lincoln Park or Wicker Park, homes can sell quickly, which gives you less time to shop after closing.
3. You may feel rushed during the buying phase
Some sellers prefer to have more time to explore neighborhoods and compare homes before committing to a purchase.
Option 2: Buy First
Buying first gives you peace of mind about where you are going before you sell your current home.
Benefits of Buying First
1. You can move without pressure
You can take your time searching for the right home and move out of your current home on your own schedule.
2. You can prepare your home for sale more easily
An empty or staged home often shows better, which can lead to:
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Higher offers
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Faster market response
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Fewer showing disruptions
3. You avoid the stress of temporary housing
Once you own your new home, you no longer have to worry about short term solutions.
Challenges of Buying First
1. You may need bridge financing or a larger down payment
To buy before selling, you need a financing plan that covers:
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The down payment for your next home
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Temporary overlap in mortgage payments
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Additional reserves as required by your lender
Bridge loans and home equity loans are common solutions but they require planning.
2. You take on more financial risk
You may carry two mortgages until your home sells, which can feel stressful if the market slows unexpectedly.
3. Strong seller markets can make contingent offers difficult
If homes in your target neighborhood sell quickly, sellers may not accept an offer that depends on your home selling first. Buying first solves this, but you must qualify financially.
Option 3: A Coordinated Approach (The Best of Both)
Many Chicago sellers use a blended strategy that minimizes risk while maximizing convenience. Your agent can help you coordinate:
A simultaneous closing
You sell your home in the morning and buy your next home in the afternoon.
A rent back agreement
You sell your home but stay for a short period after closing, giving you extra time to secure your next property.
A private pre market search
Your agent begins searching for your next home before your listing goes live, giving you a head start.
A flexible buyer timeline
Some buyers will agree to a longer closing date to accommodate your home search, especially if your home is in high demand.
This approach works particularly well in popular neighborhoods like Logan Square and Andersonville, where strong buyer activity gives sellers leverage.
How to Decide What Is Right for You
Ask yourself the following questions:
Do you need the proceeds from your current home to buy the next one?
If yes, selling first is typically the better choice.
Is your current home likely to sell quickly?
If yes, buying first may be possible with proper financial planning.
How competitive is your target neighborhood?
If you are aiming for Lincoln Park, Bucktown, or Wicker Park, homes may move fast, which can affect timing.
What is your personal tolerance for financial risk?
Buying first requires a higher risk tolerance. Selling first provides financial clarity.
How important is convenience versus control?
Your personal comfort level matters as much as market strategy.
Final Thoughts
There is no one size fits all answer to whether you should sell first or buy first in Chicago. The best choice depends on your financial situation, your neighborhood, your next home goals, and your comfort with timing and risk.
A strong agent will walk you through every option, help you evaluate local market conditions, and create a plan that protects your interests whether you sell first, buy first, or coordinate both.
Contact Camille
If you are thinking about selling your home and want expert, data driven guidance for the Chicago market, contact Camille anytime at 773.377.9200 or [email protected].
