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$309 Cheap Flights from Chicago (ORD) to Naples (NAP)

View $309 flight on Mon, Apr 26, 2027Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP)

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Cheap Flights from Chicago to Naples (ORD-NAP)

Prices were available within the past 7 days and start at $309 for one-way flights and $650 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Thu, Sep 24 - Thu, Oct 1
ORD
Chicago
NAP
Naples
$650 Roundtrip, found 7 hours ago
$650
Roundtrip
found 7 hours ago
Select TAP Portugal flight, departing Thu, Sep 24 from Chicago to Naples, returning Thu, Oct 1, priced at $650 found 7 hours ago
Scandinavian Airlines
Wed, Apr 14 - Sat, Apr 24
ORD
Chicago
NAP
Naples
$696 Roundtrip, found 1 hour ago
$696
Roundtrip
found 1 hour ago
Select Scandinavian Airlines flight, departing Wed, Apr 14 from Chicago to Naples, returning Sat, Apr 24, priced at $696 found 1 hour ago
United
Sun, Apr 18 - Thu, Apr 22
ORD
Chicago
NAP
Naples
$720 Roundtrip, found 7 hours ago
$720
Roundtrip
found 7 hours ago
Select United flight, departing Sun, Apr 18 from Chicago to Naples, returning Thu, Apr 22, priced at $720 found 7 hours ago
Lufthansa
Sun, Apr 18 - Thu, Apr 22
ORD
Chicago
NAP
Naples
$724 Roundtrip, found 7 hours ago
$724
Roundtrip
found 7 hours ago
Select Lufthansa flight, departing Sun, Apr 18 from Chicago to Naples, returning Thu, Apr 22, priced at $724 found 7 hours ago
Swiss International Air Lines
Wed, Mar 10 - Wed, Mar 24
ORD
Chicago
NAP
Naples
$726 Roundtrip, found 14 hours ago
$726
Roundtrip
found 14 hours ago
Select Swiss International Air Lines flight, departing Wed, Mar 10 from Chicago to Naples, returning Wed, Mar 24, priced at $726 found 14 hours ago
ITA Airways
Wed, Aug 19 - Wed, Aug 26
ORD
Chicago
NAP
Naples
$727 Roundtrip, found 17 hours ago
$727
Roundtrip
found 17 hours ago
Select ITA Airways flight, departing Wed, Aug 19 from Chicago to Naples, returning Wed, Aug 26, priced at $727 found 17 hours ago
American Airlines
Sun, Apr 18 - Thu, Apr 22
ORD
Chicago
NAP
Naples
$727 Roundtrip, found 7 hours ago
$727
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sun, Apr 18 from Chicago to Naples, returning Thu, Apr 22, priced at $727 found 7 hours ago
Delta
Tue, Mar 9 - Wed, Mar 17
ORD
Chicago
NAP
Naples
$728 Roundtrip, found 14 hours ago
$728
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Mar 9 from Chicago to Naples, returning Wed, Mar 17, priced at $728 found 14 hours ago
Iberia
Sun, Apr 18 - Thu, Apr 22
ORD
Chicago
NAP
Naples
$728 Roundtrip, found 7 hours ago
$728
Roundtrip
found 7 hours ago
Select Iberia flight, departing Sun, Apr 18 from Chicago to Naples, returning Thu, Apr 22, priced at $728 found 7 hours ago
British Airways
Sun, Dec 6 - Mon, Dec 14
ORD
Chicago
NAP
Naples
$729 Roundtrip, found 21 hours ago
$729
Roundtrip
found 21 hours ago
Select British Airways flight, departing Sun, Dec 6 from Chicago to Naples, returning Mon, Dec 14, priced at $729 found 21 hours ago

Alternative airports near Naples

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Naples Intl. NAP. Cheapest and Closest option available. Average driving time to city center is 10 minutes. Flights from $1,032
NAP
Naples Intl.
CheapestClosest
Average driving time to city center10 min
Flights from $1,032

What you need to know for your flight from O'Hare Intl. to Naples Intl.

Chicago (ORD) to Naples (NAP) at a glance

Embark on your journey from Chicago O'Hare International Airport (ORD) to Naples International Airport (NAP) with a range of options for Naples flights. Explore various itineraries tailored to your budget and schedule, whether you seek cheap flights to Naples or full-service experiences. With numerous airlines operating this international long-haul route, you can easily find the flight to Naples that aligns with your travel plans while discovering the enchanting sights and neighborhoods of Naples.

  • Fastest flight duration: around 9h 30m non-stop
  • Route distance: roughly 4,900 miles (7,890 km)
  • Flights per week: around 10 departures on average
  • Typical fares (one-way): economy tickets often range from $280–$880, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Naples International Airport (NAP)

Based on the latest traveler bookings, we've compiled a list of the most popular airlines flying from Chicago to Naples, focusing on both one-stop and non-stop options. Many travelers opt for layovers at Istanbul Airport (IST, approximately 1 hour and 15 minutes), Franz Josef Strauss International Airport (MUC, around 2 hours and 15 minutes), and Frankfurt International Airport (FRA, also about 2 hours and 15 minutes). This variety allows you to balance price, total travel time, and cabin class to discover the best itinerary for your trip.

  • American Airlines: This full-service airline provides non-stop flights, with one-way prices generally between $280 and $1585. It represents around 38% of the departures on this route, offering a total travel duration of 9 hours and 30 minutes.
  • United: Another full-service option, United offers one-stop flights with one-way fares ranging from $280 to $835. It makes up about 16% of departures on this route, featuring an in-flight time of 10 hours and 45 minutes, resulting in an overall journey time of approximately 12 hours and 45 minutes, including layover.
  • Turkish Airlines: This full-service carrier provides one-stop service, with one-way fares typically falling between $295 and $1270. It accounts for roughly 14% of the departures on this route, with a flying time of 10 hours and 45 minutes and a total travel duration of about 12 hours and 45 minutes, including the layover.
  • Aer Lingus: Offering one-stop service, Aer Lingus is a full-service airline with one-way fares usually between $300 and $595. It represents about 6% of departures for this route, featuring an in-flight duration of 10 hours and 45 minutes, leading to a total journey time of around 12 hours and 45 minutes, including layover.
  • ITA Airways: A full-service airline providing one-stop service, ITA Airways has one-way fares typically ranging from $425 to $905. This airline constitutes approximately 6% of departures on this route, with an in-flight time of 10 hours and 45 minutes and a total journey length of about 12 hours and 45 minutes, including layover.

Travelers flying from Chicago to Naples can opt for an upgrade. American Airlines provides both business class and premium economy service, while Turkish Airlines offers a business class option.

Best time to fly from Chicago (ORD) to Naples (NAP)

The most popular months for travelers flying from Chicago to Naples are May, June, and September, when peak temperatures in Naples reach up to 72.9°F in June. If you prefer quieter travel, consider January, the least busy time to visit with temperatures around 48°F and typically the lowest average one-way fare (around $340). Flight availability peaks in May and September, with approximately 13 flights per week, making it easier to find convenient departure times. November and December have the fewest flights, with approximately 7 flights per week.

  • Cheapest time to fly: January usually offers good deals with average one-way fare around $340, roughly 37% cheaper than the yearly average.
  • Most flight options: May and September have the highest number of flights from Chicago to Naples, with approximately 13 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January48.0°F (8.9°C)Low12$340
February48.7°F (9.3°C)Average8$431
March52.3°F (11.3°C)Average10$541
April57.6°F (14.2°C)Average9$471
May64.2°F (17.9°C)High13$591
June72.9°F (22.7°C)High11$901
July78.6°F (25.9°C)Average8$580
August79.2°F (26.2°C)Average9$470
September72.1°F (22.3°C)High13$597
October64.8°F (18.2°C)Average11$491
November57.6°F (14.2°C)Low7$518
December50.7°F (10.4°C)Low7$580

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative routes from Chicago (ORD) to Naples (NAP)

  • Chicago to Naples (MDW-NAP): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD).
  • Chicago to Salerno (ORD-QSR): Costa d'Amalfi Airport (QSR) is about 37 miles from Naples International Airport (NAP).
  • Chicago to Foggia (ORD-FOG): Gino Lisa Airport (FOG) can be found roughly 76 miles from Naples International Airport (NAP).

How to find the best prices for flights from Chicago (ORD) to Naples (NAP)

Getting some of the best deals on flights from Chicago to Naples is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking within two weeks, although most travelers tend to book at least two months in advance. Evening departures between 6 PM and 12 AM are often cheaper and are also the most popular. Additionally, flying on Wednesdays generally results in lower prices, while Fridays remain the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Naples International Airport from O'Hare International Airport

Naples welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Naples efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Naples, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Naples International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Naples International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Naples International Airport, several key transport options are conveniently located a short drive away. Nuova Poggioreale Caramanico Tram Stop, a metro station, is about 1.1 miles from the airport, while Naples Central Station, a train station, is approximately 2.3 miles away, and Naples Seaport, a seaport, is around 2.5 miles from the airport, all typically reached by car.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) cost?
You can find cheap one-way flights from $309 and cheap return flights from $650 Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) with Expedia. One-way flights usually range from $520 to $4949, and return flights typically cost between $785 and $6675. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
The cheapest month to fly from ORD to NAP is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
American Airlines offers around 7 weekly direct flights from ORD to NAP.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
American Airlines is one of the cheapest airlines offering nonstop flights from O'Hare Intl. (ORD) to Naples Intl. (NAP), with round-trip tickets starting from around $488. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
The best airline to fly with from Chicago, IL (ORD) to Naples (NAP) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. United offers the most daily flights from ORD to NAP, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
There are approximately 1 nonstop flights per day from O'Hare Intl. (ORD) to Naples Intl. (NAP). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
The earliest flight from O'Hare International Airport (ORD) to Naples International Airport (NAP) typically leaves at around 5:00 AM, operated by American Airlines. This early flight can help you make the most of your day in Naples. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
The most popular departure times for flights from O'Hare Intl. (ORD) to Naples Intl. (NAP) are from 3pm to 6pm. About 37% of passengers prefer this time window. Many major carriers, including American Airlines, Lufthansa, and United Airlines, offer flights during this window. This timing is popular as it allows you to enjoy a full day in Chicago before your evening flight.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
A nonstop flight from ORD to NAP typically takes around 9 hours 30 minutes, covering approximately 4,933 miles. Connecting flights on this route usually add 2 hours 30 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
Business class seats are offered on the ORD to NAP route. Airlines that offer business class service on this route include:

  • British Airways
  • Swiss International Air Lines
  • Lufthansa
  • TAP Portugal
  • American Airlines
  • Turkish Airlines
  • ITA Airways
  • United Airlines
  • Delta Air Lines
  • Iberia

First class is available with Swiss International Air Lines and Lufthansa.
How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
A direct, return business class ticket from Chicago, IL (ORD) to Naples (NAP) typically costs between $7,576 - $10,199. A non-stop, one-way business class flight is usually around $2,327 - $2,577. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Naples from O'Hare Intl. (ORD)?
If you're planning to travel to Naples from O'Hare Intl. (ORD), you can fly into Naples Intl. (NAP) Some flights may connect through major hubs like Pearson Intl. (YYZ), Pierre Elliott Trudeau Intl. (YUL), Logan Intl. (BOS) before reaching Naples. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) Naples Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Naples (NAP-Naples Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Naples Intl.
Airlines serving
Aer Lingus, Air Canada, Air France, American Airlines, Austrian Airlines, British Airways, Brussels Airlines, Delta, Finnair, ITA Airways, Iberia, Icelandair, JetBlue Airways, KLM, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$650
Distance
4932 mi
Average flight time
9 hours 30 mins

Book with confidence

Chicago to Naples Flights

The cheapest times to fly from Chicago to Naples

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Naples are during the month of September. You can find some of the cheapest flights from Chicago to Naples with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Naples

Sunday is one of the best days to book for cheap flights from Chicago to Naples: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Naples

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Naples in 2026. You can also book with separate airlines for your outbound and return journeys, from $309 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Naples flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Naples airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Naples Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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