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$345+ 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
Jul 4 — Jul 111
Sat 7/4
Sat 7/11
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 Sunday or Monday 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 June 4, 2026.

This United Airlines deal was found by Cheapflights users on 5/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:55 pm
ORD
-
NAP
2 stops16h 25m
United Airlines
Tue 10/206:00 am
NAP
-
ORD
2 stops15h 52m
United Airlines
Deal found 5/31$929
This Mytrip deal was found by Cheapflights users on 5/31. 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.
Sat 9/127:25 pm
ORD
-
NAP
2 stops19h 50m
Multiple Airlines
Mon 9/219:55 pm
NAP
-
ORD
3 stops28h 53m
Multiple Airlines
Deal found 5/31$930
This Kiwi.com deal was found by Cheapflights users on 6/1. 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.
Sun 9/207:25 pm
ORD
-
NAP
2 stops17h 25m
Multiple Airlines
Mon 9/2810:35 am
NAP
-
ORD
1 stop14h 15m
Multiple Airlines
Deal found 6/1$931
This Air Canada deal was found by Cheapflights users on 5/31. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:35 pm
ORD
-
NAP
2 stops17h 45m
Air Canada
Tue 10/206:00 am
NAP
-
ORD
2 stops15h 52m
Air Canada
Deal found 5/31$933
This Orbitz deal was found by Cheapflights users on 5/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:25 am
ORD
-
NAP
2 stops15h 15m
Multiple Airlines
Tue 10/207:50 pm
NAP
-
ORD
2 stops28h 30m
Multiple Airlines
Deal found 5/31$934
This Mytrip deal was found by Cheapflights users on 6/1. 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.
Tue 8/187:25 am
ORD
-
NAP
3 stops22h 25m
Multiple Airlines
Tue 8/2510:50 pm
NAP
-
ORD
2 stops22h 55m
Multiple Airlines
Deal found 6/1$935
This KAYAK deal was found by Cheapflights users on 5/31. 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.
Thu 11/264:20 pm
ORD
-
NAP
2 stops18h 05m
Lufthansa
Wed 12/26:15 pm
NAP
-
ORD
2 stops25h 55m
Lufthansa
Deal found 5/31$936
This United Airlines deal was found by Cheapflights users on 5/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:12 pm
ORD
-
NAP
2 stops21h 13m
United Airlines
Wed 12/22:15 pm
NAP
-
ORD
1 stop27h 50m
United Airlines
Deal found 5/31$938
This Mytrip deal was found by Cheapflights users on 5/31. 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.
Tue 10/138:45 am
ORD
-
NAP
3 stops29h 55m
Multiple Airlines
Tue 10/2010:50 pm
NAP
-
ORD
2 stops24h 10m
Multiple Airlines
Deal found 5/31$940
This Mytrip deal was found by Cheapflights users on 5/31. 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.
Sun 10/47:25 pm
ORD
-
NAP
3 stops30h 55m
Multiple Airlines
Sun 10/117:40 am
NAP
-
ORD
1 stop15h 15m
Multiple Airlines
Deal found 5/31$944
This KAYAK deal was found by Cheapflights users on 5/31. 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.
Wed 10/219:40 pm
ORD
-
NAP
1 stop12h 05m
Lufthansa
Sat 10/316:15 pm
NAP
-
ORD
1 stop31h 10m
Lufthansa
Deal found 5/31$945
This Mytrip deal was found by Cheapflights users on 5/31. 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.
Sun 10/47:25 pm
ORD
-
NAP
3 stops30h 55m
Multiple Airlines
Sat 10/107:50 am
NAP
-
ORD
2 stops19h 00m
Multiple Airlines
Deal found 5/31$946

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 June 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$935
(Mytrip)

One-way from

$345
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$1,235

Good round-trip deal

$1,230 or less

Good one-way deal

$938 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. 23% potential increase in price ($248 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 4, 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

Thu 9/3

10:28 am-11:05 am

2 stops17h 37m

Naples

Wed 9/16

10:05 am-4:10 pm

2 stops37h 05m

$990

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 7/29

4:40 pm-6:25 pm

1 stop18h 45m

Naples

Thu 8/6

3:05 pm-4:00 pm

2 stops31h 55m

$1,017
Quickest round-trip

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 7/29

5:30 pm-10:00 am

Nonstop9h 30m

Naples

Thu 8/6

3:00 pm-6:45 pm

Nonstop10h 45m

$1,028

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 7/29

5:30 pm-10:00 am

Nonstop9h 30m

Naples

Thu 8/6

3:00 pm-6:45 pm

Nonstop10h 45m

$1,028

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 7/19

8:40 am-7:00 am

1 stop15h 20m

Naples

Tue 8/4

9:00 am-6:15 pm

1 stop16h 15m

$1,036

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 10/4

5:25 pm-10:00 am

Nonstop9h 35m

Naples

Thu 10/15

3:00 pm-6:50 pm

Nonstop10h 50m

$1,047

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 8/10

5:30 pm-10:00 am

Nonstop9h 30m

Naples

Mon 8/17

8:25 pm-1:50 pm

1 stop24h 25m

$1,048

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 9/19

6:00 am-3:05 pm

2 stops26h 05m

Naples

Sat 9/26

8:35 pm-10:22 pm

2 stops32h 47m

$1,048

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 9/8

5:30 pm-10:00 am

Nonstop9h 30m

Naples

Wed 9/30

3:00 pm-6:50 pm

Nonstop10h 50m

$1,050

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 7/19

9:19 am-7:05 am

2 stops14h 46m

Naples

Tue 8/4

6:05 am-4:15 pm

2 stops17h 10m

$1,089

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 44 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 June.
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

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.

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 June 4, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Naples as you normally would.

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.

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 62 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 June 4, 2026.
See what other customers who have flown with SWISS,Turkish Airlines, andAer Lingus 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
1,964 reviews

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Overall

7.5

Food

7.1

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
1,964 reviews
SWISS
7.5
Good
1,964 reviews

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Overall

7.5

Food

7.1

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
4,409 reviews
SWISS
7.5
Good
1,964 reviews

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Overall

7.5

Food

7.1

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.
Aer Lingus
7.3
Good
1,595 reviews
SWISS
7.5
Good
1,964 reviews

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Overall

7.5

Food

7.1

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
11,644 reviews
SWISS
7.5
Good
1,964 reviews

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Overall

7.5

Food

7.1

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
3,224 reviews
SWISS
7.5
Good
1,964 reviews

Crew

8.3

Boarding

7.7

Entertainment

6.8

Comfort

7.4

Overall

7.5

Food

7.1

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 2 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 9h 30m. Scandinavian Airlines provides one of the quickest options available for as low as $1,028. 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 ITA Airways - these airlines can fly you to your destination from $496 and $514, respectively. Scandinavian Airlines is 44% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Chicago to Naples?

    The top 3 most reliable airlines when flying from Chicago to Naples are American Airlines (75%), Finnair (75%) and Iberia (75%).

  • What are the cheapest flights from Chicago to Naples?

    The cheapest flight price from Chicago to Naples is $796. On average you can expect to pay $1,266. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $612.

  • 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 June 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$448Average$543FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$695FlexibilityNo cancel feeOn-time69%
ITA AirwaysCheapest$514Average$822FlexibilityNo cancel feeOn-time81%
Turkish AirlinesCheapest$530Average$660FlexibilityNo cancel feeOn-time77%
IberiaCheapest$543Average$1,120FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$812FlexibilityNo cancel feeOn-time76%
British AirwaysCheapest$612Average$889FlexibilityNo cancel feeOn-time70%
Aer LingusCheapest$633Average$833FlexibilityNo cancel feeOn-timeN/A
SWISSCheapest$651Average$872FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$665Average$1,061FlexibilityNo cancel feeOn-time71%

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