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$372+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Chicago to Naples are usually found in February or March, booked 53 days in advance, depart on a Monday or Tuesday and return on a Saturday

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 April 28, 2026.

This FlightHub deal was found by Cheapflights users on 4/23. 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.
Wed 4/297:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
Thu 5/147:35 pm
NAP
-
ORD
1 stop27h 35m
Scandinavian Airlines
Deal found 4/23$796
This oojo deal was found by Cheapflights users on 4/27. 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.
Sat 9/57:15 pm
ORD
-
NAP
1 stop12h 50m
Scandinavian Airlines
Wed 9/1610:05 am
NAP
-
ORD
2 stops37h 05m
Scandinavian Airlines
Deal found 4/27$798
This Booking.com deal was found by Cheapflights users on 4/24. 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.
Sat 11/2111:50 am
ORD
-
NAP
1 stop23h 35m
Turkish Airlines
Sat 11/289:15 am
NAP
-
ORD
1 stop16h 10m
Turkish Airlines
Deal found 4/24$799
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Thu 9/311:25 am
ORD
-
NAP
1 stop20h 20m
Turkish Airlines
Tue 9/89:30 am
NAP
-
ORD
1 stop31h 10m
Turkish Airlines
Deal found 4/25$801
This oojo deal was found by Cheapflights users on 4/26. 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.
Sat 9/58:10 pm
ORD
-
NAP
1 stop35h 25m
Turkish Airlines
Wed 9/163:45 pm
NAP
-
ORD
1 stop24h 55m
Turkish Airlines
Deal found 4/26$802
This Scandinavian Airlines deal was found by Cheapflights users on 4/25. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
Tue 9/157:45 pm
NAP
-
ORD
2 stops33h 21m
Scandinavian Airlines
Deal found 4/25$804
This KAYAK deal was found by Cheapflights users on 4/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:10 pm
ORD
-
NAP
1 stop16h 35m
Turkish Airlines
Tue 9/228:45 pm
NAP
-
ORD
1 stop19h 55m
Turkish Airlines
Deal found 4/24$805
This KAYAK deal was found by Cheapflights users on 4/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:10 pm
ORD
-
NAP
1 stop16h 35m
Turkish Airlines
Sat 10/317:25 pm
NAP
-
ORD
1 stop22h 40m
Turkish Airlines
Deal found 4/24$807
This Scandinavian Airlines deal was found by Cheapflights users on 4/24. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
-
NAP
2 stops21h 05m
Scandinavian Airlines
Tue 8/257:45 pm
NAP
-
ORD
2 stops33h 21m
Scandinavian Airlines
Deal found 4/24$808
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Wed 9/238:10 pm
ORD
-
NAP
1 stop35h 35m
Turkish Airlines
Sat 10/108:45 pm
NAP
-
ORD
1 stop19h 55m
Turkish Airlines
Deal found 4/23$811
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:10 pm
ORD
-
NAP
1 stop16h 35m
Turkish Airlines
Thu 9/178:45 pm
NAP
-
ORD
1 stop19h 55m
Turkish Airlines
Deal found 4/24$812
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:25 pm
ORD
-
NAP
2 stops19h 35m
Multiple Airlines
Fri 10/2311:40 am
NAP
-
ORD
1 stop14h 35m
Multiple Airlines
Deal found 4/24$813

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$821
(FlightHub)

One-way from

$373
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$831

Good round-trip deal

$1,170 or less

Good one-way deal

$834 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 ($212 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 28, 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

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

9:30 am-11:30 am

2 stops19h 00m

Naples

Fri 8/21

6:05 am-9:46 pm

2 stops22h 41m

$831

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/11

6:00 am-8:10 am

2 stops19h 10m

Naples

Sat 8/22

6:05 am-9:46 pm

2 stops22h 41m

$831

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/18

6:00 am-7:05 am

1 stop18h 05m

Naples

Tue 8/25

6:05 am-6:05 pm

2 stops19h 00m

$876

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 8/31

7:15 pm-9:15 am

2 stops31h 00m

Naples

Wed 9/9

10:05 am-4:10 pm

2 stops37h 05m

$893

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 9/3

7:00 am-11:05 am

2 stops21h 05m

Naples

Tue 9/8

7:45 pm-10:06 pm

2 stops33h 21m

$973

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 8/12

5:25 pm-10:00 am

Nonstop9h 35m

Naples

Fri 8/21

8:05 pm-1:50 pm

1 stop24h 45m

$985

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 7/29

5:25 pm-10:00 am

Nonstop9h 35m

Naples

Thu 8/6

7:40 am-6:15 pm

1 stop17h 35m

$1,048

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 7/26

1:18 pm-12:05 pm

2 stops15h 47m

Naples

Wed 8/5

6:00 am-4:53 pm

2 stops17h 53m

$1,057

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 8/31

5:59 pm-6:15 pm

2 stops17h 16m

Naples

Wed 9/9

9:05 am-9:46 pm

1 stop19h 41m

$1,069
Quickest round-trip

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 7/13

7:05 pm-2:00 pm

1 stop11h 55m

Naples

Thu 7/23

9:30 am-3:55 pm

1 stop13h 25m

$1,086

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 40 resultsSorted by cheapest first
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice 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?

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 64 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, May is the cheapest month in which you can book a flight from Chicago to Naples (average of $371). Flying from Chicago to Naples in June is currently the most expensive (average of $740). 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 much does it cost to fly round-trip from Chicago to Naples?

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 April 28, 2026.
See what other customers who have flown with SWISS,Turkish Airlines, andAmerican 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
1,924 reviews

Comfort

7.4

Boarding

7.7

Food

7.1

Crew

8.3

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
SWISS
7.5
Good
1,924 reviews
SWISS
7.5
Good
1,924 reviews

Comfort

7.4

Boarding

7.7

Food

7.1

Crew

8.3

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
Turkish Airlines
7.4
Good
4,341 reviews
SWISS
7.5
Good
1,924 reviews

Comfort

7.4

Boarding

7.7

Food

7.1

Crew

8.3

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
American Airlines
7.1
Good
11,676 reviews
SWISS
7.5
Good
1,924 reviews

Comfort

7.4

Boarding

7.7

Food

7.1

Crew

8.3

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
Iberia
7.0
Good
3,202 reviews
SWISS
7.5
Good
1,924 reviews

Comfort

7.4

Boarding

7.7

Food

7.1

Crew

8.3

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.
British Airways
6.7
Okay
7,928 reviews
SWISS
7.5
Good
1,924 reviews

Comfort

7.4

Boarding

7.7

Food

7.1

Crew

8.3

Overall

7.5

Entertainment

6.8

Reviews

1 / 20
6.0
Good

CFJ,Mar 2026

ZRH - VCE

Swiss International Airlines is heading towards becoming a budget carrier. The seats are in comfortable and have absolutely no recline. The crew are friendly, but offer a few services. At least they all line is usually punctual.

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 15h 47m. Delta provides one of the quickest options available for as low as $1,057. 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 Turkish Airlines - 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 $552. On average you can expect to pay $1,176. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $641.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Naples (average of $371). Flying from Chicago to Naples in June is currently the most expensive (average of $740). 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

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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
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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$448Average$543FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$695FlexibilityNo cancel feeOn-time69%
Turkish AirlinesCheapest$530Average$646FlexibilityNo cancel feeOn-time77%
IberiaCheapest$543Average$1,118FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$796FlexibilityNo cancel feeOn-time76%
British AirwaysCheapest$608Average$861FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$614Average$1,031FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$626Average$832FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$629Average$949FlexibilityNo cancel feeOn-time81%
SWISSCheapest$651Average$872FlexibilityNo cancel feeOn-time79%

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