$383 Cheap Flights from Chicago (ORD) to Naples (NAP)

View $383 flight on Sun, Aug 10, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Naples (ORD-NAP)

Prices were available within the past 7 days and start at $383 for one-way flights and $482 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Mon, Sep 1 - Sun, Sep 7
ORD
Chicago
NAP
Naples
$482 Roundtrip, found 4 hours ago
$482
Roundtrip
found 4 hours ago
Select Scandinavian Airlines flight, departing Mon, Sep 1 from Chicago to Naples, returning Sun, Sep 7, priced at $482 found 4 hours ago
Delta
Mon, Sep 22 - Thu, Oct 16
ORD
Chicago
NAP
Naples
$546 Roundtrip, found 1 day ago
$546
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 22 from Chicago to Naples, returning Thu, Oct 16, priced at $546 found 1 day ago
TAP Portugal
Mon, Sep 15 - Thu, Sep 25
ORD
Chicago
NAP
Naples
$550 Roundtrip, found 13 hours ago
$550
Roundtrip
found 13 hours ago
Select TAP Portugal flight, departing Mon, Sep 15 from Chicago to Naples, returning Thu, Sep 25, priced at $550 found 13 hours ago
Iberia
Wed, Nov 5 - Wed, Nov 12
ORD
Chicago
NAP
Naples
$592 Roundtrip, found 2 days ago
$592
Roundtrip
found 2 days ago
Select Iberia flight, departing Wed, Nov 5 from Chicago to Naples, returning Wed, Nov 12, priced at $592 found 2 days ago
United
Wed, Oct 29 - Wed, Nov 19
ORD
Chicago
NAP
Naples
$607 Roundtrip, found 4 hours ago
$607
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Oct 29 from Chicago to Naples, returning Wed, Nov 19, priced at $607 found 4 hours ago
Lufthansa
Tue, Nov 25 - Tue, Dec 2
ORD
Chicago
NAP
Naples
$607 Roundtrip, found 6 hours ago
$607
Roundtrip
found 6 hours ago
Select Lufthansa flight, departing Tue, Nov 25 from Chicago to Naples, returning Tue, Dec 2, priced at $607 found 6 hours ago
Air Canada
Tue, Feb 24 - Wed, Mar 4
ORD
Chicago
NAP
Naples
$611 Roundtrip, found 3 days ago
$611
Roundtrip
found 3 days ago
Select Air Canada flight, departing Tue, Feb 24 from Chicago to Naples, returning Wed, Mar 4, priced at $611 found 3 days ago
ITA Airways
Wed, May 7 - Tue, May 13
ORD
Chicago
NAP
Naples
$611 Roundtrip, found 22 hours ago
$611
Roundtrip
found 22 hours ago
Select ITA Airways flight, departing Wed, May 7 from Chicago to Naples, returning Tue, May 13, priced at $611 found 22 hours ago
Austrian Airlines
Tue, Mar 10 - Mon, Mar 16
ORD
Chicago
NAP
Naples
$612 Roundtrip, found 3 days ago
$612
Roundtrip
found 3 days ago
Select Austrian Airlines flight, departing Tue, Mar 10 from Chicago to Naples, returning Mon, Mar 16, priced at $612 found 3 days ago
KLM
Mon, Sep 22 - Thu, Oct 16
ORD
Chicago
NAP
Naples
$614 Roundtrip, found 1 day ago
$614
Roundtrip
found 1 day ago
Select KLM flight, departing Mon, Sep 22 from Chicago to Naples, returning Thu, Oct 16, priced at $614 found 1 day ago
Flights from Chicago (ORD) to Naples (NAP)
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, Emirates, Finnair, ITA Airways, Iberia, JetBlue Airways, KLM, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$481
Distance
4932 mi

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 2025. You can also book with separate airlines for your outbound and return journeys, from $383 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.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP) cost?
Cheap round-trip flights from O’Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP) start from $1002. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving ORD on May 19 2025 and touching down at NAP. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from ORD to NAP?
The cheapest flights from ORD to NAP are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to NAP?
With tickets starting at $651 for a one-way flight from ORD to NAP, American Airlines is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 15 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP)?
There are no daily direct flights departing from O’Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you’ll be on your way before you know it.
What day of the week has the most flights from ORD to NAP?
You’ll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP)?
To arrive at Naples Intl. Airport (NAP) on time, book a flight that leaves O’Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP) last-minute?
Last-minute fares from ORD to NAP are usually more expensive. To secure the lowest rates, start searching for flights ahead of time. That being said, if you can play around with your travel dates, it’s possible to land a cheap ticket right before your trip.
Is it cheaper to book an ORD to NAP flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to NAP flight and hotel package with Expedia could lead to significant savings. What’s more, having everything in one easy place will take the hassle out of travel planning. Simply secure your flights and choose from our wide range of hotels, then personalize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Naples Intl. Airport (NAP)?
If you reserved your ORD to NAP flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

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*Available to One Key members.