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Cheap flights from Chicago (CHI) to Naples, FL (APF)

CHI — APF
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Chicago to Naples

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Naples (APF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 31, 2025.

Popular in

November

Cheapest in

February

Average price

$230
Highest demand for flights based on searches. 27% potential increase in price ($124 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Best time to book a flight from Chicago to Naples

Have a flexible travel schedule? Discover the best time to fly to Naples from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Naples

What is the cheapest month to book a flight from Chicago to Naples, Florida?

Currently, September is the cheapest month in which you can book a flight from Chicago to Naples, Florida (average of $192). Flying from Chicago to Naples, Florida in July is currently the most expensive (average of $296). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to APF?

Find hourly flight availability from Chicago to Naples. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

One of the essential ways to save on airfare from Chicago to Naples, Florida is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 45% on airfare.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Naples. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Naples from Chicago?

    For a flight from Chicago to Naples, you will be flying into Naples. Naples (APF) is just 1.5 mi from the center of the city. Naples is the only Naples airport and it handles 0 inbound flights from Chicago per day. 1 airline has flights to Naples from Chicago on a regular basis.

  • Can I find deals for flights from Chicago to Naples that include hotel bookings?

    Yes. In addition to deals on Chicago to Naples flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Naples?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Naples.

  • Can I find deals for business class flights from Chicago to Naples?

    Yes. Cheapflights offers flight deals from Chicago to Naples by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Naples, Florida?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Naples, Florida (average of $192). Flying from Chicago to Naples, Florida in July is currently the most expensive (average of $296). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top airline flying from Chicago to Naples

Discover the top airline that operate flights from Chicago to Naples. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$370FlexibilityNo cancel feeOn-time65%

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