HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Naples

$251+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
apr. 12 — apr. 191
zo 4/12
zo 4/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Naples with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to Naples are usually found in February or March, booked 52 days in advance, depart on a Tuesday or Monday and return on a Wednesday

Cheap 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 maart 13, 2026.

This lol.travel deal was found by Cheapflights users on 3/9. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 4/257:15 pm
ORD
-
NAP
1 stop12h 50m
Scandinavian Airlines
vr 5/811:55 am
NAP
-
ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 3/9$446
This oojo deal was found by Cheapflights users on 3/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 4/297:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
do 5/1411:55 am
NAP
-
ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 3/9$451
This lol.travel deal was found by Cheapflights users on 3/11. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
zo 4/196:00 pm
ORD
-
NAP
1 stop17h 20m
TAP AIR PORTUGAL
di 5/512:30 pm
NAP
-
ORD
1 stop34h 30m
TAP AIR PORTUGAL
Deal found 3/11$504
This FlightHub deal was found by Cheapflights users on 3/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 10/1311:25 am
ORD
-
NAP
1 stop25h 20m
Turkish Airlines
di 10/279:15 am
NAP
-
ORD
1 stop31h 50m
Turkish Airlines
Deal found 3/12$520
This FlightHub deal was found by Cheapflights users on 3/9. 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.
zo 10/48:10 pm
ORD
-
NAP
1 stop16h 35m
Turkish Airlines
do 10/159:30 am
NAP
-
ORD
1 stop31h 10m
Turkish Airlines
Deal found 3/9$521
This FlightHub deal was found by Cheapflights users on 3/9. 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.
di 9/2211:25 am
ORD
-
NAP
1 stop14h 05m
Turkish Airlines
di 9/299:30 am
NAP
-
ORD
1 stop31h 10m
Turkish Airlines
Deal found 3/9$523
This FlightHub deal was found by Cheapflights users on 3/9. 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.
do 4/238:10 pm
ORD
-
NAP
1 stop29h 20m
Turkish Airlines
di 5/58:45 pm
NAP
-
ORD
1 stop19h 55m
Turkish Airlines
Deal found 3/9$529
This Booking.com deal was found by Cheapflights users on 3/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 4/218:10 pm
ORD
-
NAP
1 stop29h 20m
Turkish Airlines
di 4/288:45 pm
NAP
-
ORD
1 stop19h 55m
Turkish Airlines
Deal found 3/8$531
This Delta deal was found by Cheapflights users on 3/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 8/1810:35 am
MDW
-
NAP
2 stops17h 55m
Delta
wo 8/269:05 am
NAP
-
MDW
1 stop19h 41m
Delta
Deal found 3/9$718
This KLM deal was found by Cheapflights users on 3/9. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 8/125:25 pm
MDW
-
NAP
1 stop30h 40m
KLM
vr 8/219:05 am
NAP
-
MDW
1 stop19h 41m
KLM
Deal found 3/9$720
This Delta deal was found by Cheapflights users on 3/10. 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.
di 8/1810:35 am
MDW
-
NAP
2 stops17h 55m
Delta
di 8/256:05 am
NAP
-
MDW
2 stops19h 26m
Delta
Deal found 3/10$729
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 8/175:25 pm
MDW
-
NAP
2 stops17h 50m
Delta
ma 8/246:05 am
NAP
-
MDW
2 stops19h 26m
Delta
Deal found 3/12$730

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 (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 maart 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$446
(lol.travel)

One-way from

$251
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$572

Good round-trip deal

$884 or less

Good one-way deal

$726 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. 20% potential increase in price ($218 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 maart 13, 2026.
Use the filters below to find and compare flights from Chicago to Naples that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

ma 4/13

7:15 pm-6:45 pm

1 stop16h 30m

Naples

vr 4/17

11:55 am-4:10 pm

1 stop35h 15m

$649

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

za 4/25

6:00 am-8:10 am

2 stops19h 10m

Naples

vr 5/8

6:05 am-6:33 pm

2 stops19h 28m

$904

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

ma 4/13

8:58 am-11:40 am

2 stops19h 42m

Naples

vr 4/17

12:35 pm-4:05 pm

1 stop34h 30m

$965

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

ma 4/13

7:25 pm-6:50 pm

2 stops16h 25m

Naples

vr 4/17

11:20 am-9:25 pm

2 stops17h 05m

$1,039

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

za 5/2

4:55 pm-2:05 pm

1 stop14h 10m

Naples

zo 5/10

3:00 pm-6:55 pm

Nonstop10h 55m

$1,074

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

di 4/28

10:41 am-11:30 am

2 stops17h 49m

Naples

zo 5/3

6:05 am-5:58 pm

2 stops18h 53m

$1,091

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

di 3/17

6:01 pm-10:55 pm

3 stops22h 54m

Naples

do 3/19

12:15 pm-4:00 pm

2 stops33h 45m

$1,092

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

za 5/9

9:22 am-11:20 am

2 stops18h 58m

Naples

za 5/16

6:05 am-5:56 pm

2 stops18h 51m

$1,102
Quickest round-trip

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

ma 6/8

5:30 pm-10:00 am

Nonstop9h 30m

Naples

wo 6/17

3:00 pm-6:55 pm

Nonstop10h 55m

$1,155

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

wo 5/13

1:22 pm-3:45 pm

2 stops19h 23m

Naples

do 5/21

6:05 am-9:09 pm

2 stops22h 04m

$1,179

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 34 resultsSorted by cheapest first
1
2
3
4

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Naples flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 March 6, 2026.

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.

How often are flights from Chicago to Naples delayed?

About 32% of weekly flights between Chicago and Naples have experienced delays in the past year, with the average delay time being 174 minutes.

What is the most punctual flight time for Chicago to Naples flights?

Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Naples flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 32% of flights being delayed.

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 maart 13, 2026.
See what other customers who have flown with SWISS,United Airlines, andTurkish 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.
SWISS
7.5
Good
1,897 reviews

Food

7.1

Overall

7.5

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
SWISS
7.5
Good
1,897 reviews
SWISS
7.5
Good
1,897 reviews

Food

7.1

Overall

7.5

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
United Airlines
7.4
Good
9,423 reviews
SWISS
7.5
Good
1,897 reviews

Food

7.1

Overall

7.5

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
Turkish Airlines
7.3
Good
4,253 reviews
SWISS
7.5
Good
1,897 reviews

Food

7.1

Overall

7.5

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
American Airlines
7.1
Good
11,464 reviews
SWISS
7.5
Good
1,897 reviews

Food

7.1

Overall

7.5

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
British Airways
6.7
Okay
7,786 reviews
SWISS
7.5
Good
1,897 reviews

Food

7.1

Overall

7.5

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.

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. 11 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 16h 30m. Scandinavian Airlines provides one of the quickest options available for as low as $649. 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 $448, 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 Iberia - these airlines can fly you to your destination from $496 and $530, respectively. Scandinavian Airlines is 45% 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 $604. On average you can expect to pay $1,030. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $523.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
St. Louis to Naples flights

Top 10 airlines flying from Chicago to Naples

Discover the top 10 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 maart 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$448Average$522FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$808FlexibilityNo cancel feeOn-time69%
IberiaCheapest$530Average$890FlexibilityNo cancel feeOn-time77%
Turkish AirlinesCheapest$536Average$643FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$812FlexibilityNo cancel feeOn-time76%
FinnairCheapest$600Average$1,278FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$871FlexibilityNo cancel feeOn-time79%
British AirwaysCheapest$605Average$861FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$625Average$1,071FlexibilityNo cancel feeOn-time71%
ITA AirwaysCheapest$629Average$975FlexibilityNo cancel feeOn-time81%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.