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$219+ Cheap flights from Chicago (CHI) to Naples (NAP)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Find cheap flights from Chicago to Naples with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Naples are usually found in February or January, booked 52 days in advance, depart on a Monday or Tuesday and return on a Saturday

Find flight deals from Chicago to Naples

Cheapest flights from Chicago to Naples
Explore the most affordable flight options available from Chicago to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 12, 2025.

This lol.travel deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Mon 12/153:00 pmNAP - ORD
1 stop32h 20mMultiple Airlines
Deal found 11/12$520
This American Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/13:03 pmORD - NAP
2 stops16h 07mAmerican Airlines
Mon 12/151:55 pmNAP - ORD
1 stop32h 30mAmerican Airlines
Deal found 11/12$559
This Trip.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/11:47 pmMDW - NAP
2 stops19h 03mKLM
Mon 12/158:50 pmNAP - MDW
2 stops28h 10mKLM
Deal found 11/12$571
This FlightHub deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:50 pmORD - NAP
1 stop12h 35mMultiple Airlines
Sun 12/73:00 pmNAP - ORD
1 stop32h 20mMultiple Airlines
Deal found 11/9$580
This Air France deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:20 pmORD - NAP
1 stop15h 30mAir France
Sun 12/711:50 amNAP - ORD
1 stop33h 30mAir France
Deal found 11/11$584
This FlightHub deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2810:35 pmORD - NAP
1 stop12h 40mMultiple Airlines
Fri 12/510:10 amNAP - ORD
1 stop13h 10mMultiple Airlines
Deal found 11/10$593
This oojo deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:20 pmORD - NAP
1 stop16h 20mScandinavian Airlines
Sun 12/147:25 pmNAP - ORD
1 stop28h 20mScandinavian Airlines
Deal found 11/10$598
This Cheapflightsfares deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:50 pmORD - NAP
1 stop12h 35mLufthansa
Sun 12/76:15 pmNAP - ORD
2 stops25h 55mLufthansa
Deal found 11/11$601
This Mytrip deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:50 pmORD - NAP
2 stops17h 45mMultiple Airlines
Sun 12/148:10 amNAP - ORD
2 stops16h 45mMultiple Airlines
Deal found 11/10$618
This oojo deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:48 amORD - NAP
2 stops16h 47mITA Airways
Wed 11/196:35 amNAP - ORD
2 stops18h 35mITA Airways
Deal found 11/11$625
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/289:34 amMDW - NAP
2 stops18h 36mDelta
Fri 12/56:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 11/10$660
This Trip.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/299:34 amMDW - NAP
2 stops17h 01mKLM
Sun 12/149:35 pmNAP - MDW
2 stops27h 25mKLM
Deal found 11/10$684

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 (NAP). 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 November 12, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$446
(Booking.com)

One-way from

$219
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$756

Good round-trip deal

$816 or less

Good one-way deal

$723 or less
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
From Chicago (CHI) to Naples
Search Deals
One-way flight from Chicago (CHI) to Naples
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($257 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Naples.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Naples.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Naples that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 12, 2025.
Use the filters below to find and compare flights from Chicago to Naples that are best for you.

Fly from

Chicago

Fly to

Naples

Route

Depart

Return

Price

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/1

6:30 pm-4:55 pm

2 stops15h 25m

Naples

Thu 2/5

10:25 pm-5:20 pm

2 stops25h 55m

$496

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/25

6:50 pm-2:10 pm

1 stop12h 20m

Naples

Fri 2/13

10:10 am-4:20 pm

1 stop13h 10m

$540

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/1

6:50 pm-2:10 pm

1 stop12h 20m

Naples

Wed 2/25

9:50 am-4:20 pm

1 stop13h 30m

$540

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 5/9

7:15 pm-3:05 pm

1 stop12h 50m

Naples

Thu 5/14

7:35 pm-4:10 pm

1 stop27h 35m

$549

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 3/2

9:34 am-3:50 pm

2 stops23h 16m

Naples

Wed 3/11

6:15 am-6:34 pm

2 stops18h 19m

$555

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 2/4

12:48 pm-11:30 am

2 stops15h 42m

Naples

Wed 2/11

6:15 am-5:32 pm

2 stops18h 17m

$555

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 2/4

8:45 am-5:25 pm

2 stops25h 40m

Naples

Mon 2/23

2:15 pm-6:41 pm

2 stops35h 26m

$569

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 4/5

6:00 pm-6:20 pm

1 stop17h 20m

Naples

Thu 4/9

7:15 pm-4:00 pm

1 stop27h 45m

$583

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 1/31

6:17 pm-1:25 pm

2 stops36h 08m

Naples

Mon 2/23

2:15 pm-6:41 pm

2 stops35h 26m

$586

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/1

6:50 pm-2:10 pm

1 stop12h 20m

Naples

Sat 2/21

10:00 am-4:20 pm

1 stop13h 20m

$590

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 31 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
MytripPrice 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 flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago-Naples flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Chicago-Naples flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Naples flights, Cheapflights users trust Mytrip the most. Mytrip 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 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

How far ahead should I book a flight from Chicago to Naples?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Naples. Price data was last updated on November 7, 2025.

The price you pay for your flight from Chicago to Naples may vary depending on when you book. For the best chance of a lower fare, look to book 52 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, March is the cheapest month in which you can book a flight from Chicago to Naples (average of $496). Flying from Chicago to Naples in June is currently the most expensive (average of $816). 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 NAP?

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 November 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Naples in the morning. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago to Naples?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Naples. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Naples flight should consider departing on Sunday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 12, 2025.
See what other customers who have flown with United Airlines, Turkish Airlines, and American Airlines from Chicago to Naples have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,015 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,015 reviews
United Airlines
7.4
Good
9,015 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Turkish Airlines
7.3
Good
4,043 reviews
United Airlines
7.4
Good
9,015 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,049 reviews
United Airlines
7.4
Good
9,015 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Aer Lingus
7.2
Good
1,370 reviews
United Airlines
7.4
Good
9,015 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
ITA Airways
6.7
Okay
1,082 reviews
United Airlines
7.4
Good
9,015 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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?

    Naples (NAP), located 2.9 mi from the city center, is the airport you fly into when you book flights from Chicago to Naples. 9 airlines have flights to Naples from Chicago on a regular basis. Booking flights from Chicago to Naples should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Naples?

    A quick flight from Chicago to Naples can take about 12h 20m. SWISS provides one of the quickest options available for as low as $540. There are 4929 mi between Chicago and Naples. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Naples round-trip?

    Currently priced at $414, Scandinavian Airlines will fly you from Chicago to Naples and back. In addition to Scandinavian Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and British Airways - these airlines can fly you to your destination from $496 and $497, respectively. Scandinavian Airlines is 51% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from Chicago to Naples?

    The cheapest flight price from Chicago to Naples is $626. On average you can expect to pay $871. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $446.

  • 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?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Naples (average of $496). Flying from Chicago to Naples in June is currently the most expensive (average of $816). 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.

See more FAQs

Traveling to a place near Naples?

Book flights to Naples if you plan to visit one of these locations
Praiano
Ravello
Conca Dei Marini
Maiori
Sant'Agnello
Vico Equense

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Alternative routes for Chicago to Naples

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Naples flights
Midway to Naples flights
St. Louis to Naples flights

Top 9 airlines flying from Chicago to Naples

Discover the top 9 airlines 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$522FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$814FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$497Average$838FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$524Average$623FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$744FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$890FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$631Average$1,114FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$634Average$858FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$1,011FlexibilityNo cancel feeOn-time81%

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