HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Naples

$217+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Feb 16 — Feb 231
Mon 2/16
Mon 2/23
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 January, booked 52 days in advance, depart on a Tuesday or Monday and return on a Saturday

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 January 17, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$411
(oojo)

One-way from

$217
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$622

Good round-trip deal

$827 or less

Good one-way deal

$631 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. 21% potential increase in price ($238 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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

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 January 17, 2026.

This oojo deal was found by Cheapflights users on 1/17. 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 4/296:00 pm
ORD
-
NAP
1 stop17h 25m
TAP AIR PORTUGAL
Thu 5/147:15 pm
NAP
-
ORD
1 stop27h 45m
TAP AIR PORTUGAL
Deal found 1/17$411
This oojo deal was found by Cheapflights users on 1/16. 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.
Fri 5/16:00 pm
ORD
-
NAP
1 stop17h 20m
TAP AIR PORTUGAL
Fri 5/812:30 pm
NAP
-
ORD
1 stop34h 45m
TAP AIR PORTUGAL
Deal found 1/16$418
This FlightHub deal was found by Cheapflights users on 1/16. 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 5/16:00 pm
ORD
-
NAP
1 stop17h 20m
TAP AIR PORTUGAL
Thu 5/77:15 pm
NAP
-
ORD
1 stop27h 45m
TAP AIR PORTUGAL
Deal found 1/16$428
This KAYAK deal was found by Cheapflights users on 1/16. 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 4/176:00 pm
ORD
-
NAP
1 stop17h 20m
TAP AIR PORTUGAL
Fri 4/2412:30 pm
NAP
-
ORD
1 stop34h 45m
TAP AIR PORTUGAL
Deal found 1/16$446
This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Sat 4/187:15 pm
ORD
-
NAP
1 stop12h 50m
Scandinavian Airlines
Thu 4/237:35 pm
NAP
-
ORD
1 stop27h 35m
Scandinavian Airlines
Deal found 1/16$452
This Scandinavian Airlines deal was found by Cheapflights users on 1/16. 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 4/157:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
Thu 4/237:35 pm
NAP
-
ORD
1 stop27h 35m
Scandinavian Airlines
Deal found 1/16$456
This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Mon 3/29:50 pm
ORD
-
NAP
1 stop12h 35m
Lufthansa
Mon 3/96:15 pm
NAP
-
ORD
1 stop31h 10m
Lufthansa
Deal found 1/16$479
This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Wed 4/157:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
Fri 4/2411:55 am
NAP
-
ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 1/16$482
This FlightHub deal was found by Cheapflights users on 1/16. 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.
Sat 4/187:15 pm
ORD
-
NAP
1 stop12h 50m
Scandinavian Airlines
Fri 4/2411:55 am
NAP
-
ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 1/16$484
This oojo deal was found by Cheapflights users on 1/16. 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.
Fri 4/246:00 pm
ORD
-
NAP
1 stop17h 20m
TAP AIR PORTUGAL
Fri 5/112:30 pm
NAP
-
ORD
1 stop34h 45m
TAP AIR PORTUGAL
Deal found 1/16$489
This Cheapflightsfares deal was found by Cheapflights users on 1/17. 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.
Wed 2/256:50 pm
ORD
-
NAP
1 stop12h 25m
SWISS
Wed 3/49:50 am
NAP
-
ORD
1 stop13h 30m
SWISS
Deal found 1/17$490
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 2/14:05 pm
ORD
-
NAP
1 stop14h 20m
Lufthansa
Tue 2/176:15 pm
NAP
-
ORD
1 stop31h 10m
Lufthansa
Deal found 1/16$491

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 January 17, 2026.
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

Wed 4/29

6:00 pm-6:25 pm

1 stop17h 25m

Naples

Thu 5/14

7:15 pm-4:00 pm

1 stop27h 45m

$411

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 4/15

7:15 pm-6:45 pm

1 stop16h 30m

Naples

Thu 4/23

7:35 pm-4:10 pm

1 stop27h 35m

$456

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/15

5:10 pm-1:05 pm

1 stop12h 55m

Naples

Tue 3/3

6:20 am-2:55 pm

1 stop15h 35m

$509

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/15

6:08 am-1:05 pm

2 stops23h 57m

Naples

Tue 3/3

12:40 pm-1:50 pm

1 stop32h 10m

$514

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 2/1

1:26 pm-12:25 pm

2 stops15h 59m

Naples

Tue 2/17

6:15 am-5:45 pm

2 stops18h 30m

$525

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 4/15

11:25 am-8:25 am

1 stop14h 00m

Naples

Wed 4/29

9:25 am-6:15 pm

1 stop15h 50m

$535

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 4/17

3:57 pm-10:00 pm

2 stops23h 03m

Naples

Thu 4/23

7:40 am-1:50 pm

1 stop13h 10m

$569

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 3/3

6:20 pm-3:50 pm

2 stops14h 30m

Naples

Mon 3/9

6:15 am-6:40 pm

2 stops18h 25m

$578

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 2/4

11:50 am-6:25 pm

1 stop23h 35m

Naples

Sun 2/8

9:15 am-10:05 am

1 stop31h 50m

$583

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 3/20

1:06 pm-6:15 pm

2 stops23h 09m

Naples

Mon 3/23

2:15 pm-12:10 pm

1 stop27h 55m

$595

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 26 results
1
2
3

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 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 January 16, 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 January 17, 2026.
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
9,171 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,171 reviews
United Airlines
7.4
Good
9,171 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Turkish Airlines
7.3
Good
4,186 reviews
United Airlines
7.4
Good
9,171 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,154 reviews
United Airlines
7.4
Good
9,171 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Aer Lingus
7.2
Good
1,435 reviews
United Airlines
7.4
Good
9,171 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
ITA Airways
6.7
Okay
1,128 reviews
United Airlines
7.4
Good
9,171 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 16h 30m. TAP AIR PORTUGAL provides one of the quickest options available for as low as $456. 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 airlines to fly from Chicago to Naples one-way?

    $378 is the cheapest one-way deal found within the past few days, from Turkish Airlines. You may also be able to find cheap deals on Scandinavian Airlines and American Airlines, with prices starting from $430 and $438, respectively.

  • What are the cheapest flights from Chicago to Naples?

    The cheapest flight price from Chicago to Naples is $611. On average you can expect to pay $793. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $411.

  • 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
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 January 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$502FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$496Average$808FlexibilityNo cancel feeOn-time69%
British AirwaysCheapest$497Average$838FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$530Average$632FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$575Average$796FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$733FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$628Average$1,103FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$634Average$858FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$713Average$1,011FlexibilityNo 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.
Site
©2026 Cheapflights