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

CHI — APF
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Find 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Popular in

March

Cheapest in

September

Average price

$330
Provider with most accurate pricing for Chicago (CHI)-Naples flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Naples flights.
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Compare providers for flights from Chicago to Naples

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Naples in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Naples, Florida flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Naples, Florida flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Naples, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Naples, Florida flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Naples, Florida flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, March is the cheapest month in which you can book a flight from Chicago to Naples, Florida (average of $44). Flying from Chicago to Naples, Florida in June is currently the most expensive (average of $101). 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 December 4, 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 afternoon could potentially save you up to 35% on airfare.

Reviews of airlines servicing Naples

Get insights into the airlines that provide service to Naples. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Naples. Reviews last updated December 4, 2025.
Peruse reviews from past customers who have flown with United Airlines and Spirit Airlines from Chicago to Naples to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,066 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,066 reviews
United Airlines
7.4
Good
9,066 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Spirit Airlines
6.3
Okay
8,157 reviews
United Airlines
7.4
Good
9,066 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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.

  • What is the cheapest airline to fly from Chicago to Naples, Florida round-trip?

    Flying on Spirit Airlines is currently your cheapest option to Naples, Florida, with prices starting at $133.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Naples, Florida (average of $44). Flying from Chicago to Naples, Florida in June is currently the most expensive (average of $101). 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$324FlexibilityNo cancel feeOn-time65%

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