$604 Cheap Flights from Naples (NAP) to Chicago (ORD)

View $604 flight on Wed, Oct 1, 2025Opens in a new window

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

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Cheap Flights from Naples to Chicago (NAP-ORD)

Prices were available within the past 7 days and start at $604 for one-way flights and $400 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Thu, Sep 25 - Sat, Oct 4
NAP
Naples
ORD
Chicago
$400 Roundtrip, found 6 days ago
$400
Roundtrip
found 6 days ago
Select TAP Portugal flight, departing Thu, Sep 25 from Naples to Chicago, returning Sat, Oct 4, priced at $400 found 6 days ago
Scandinavian Airlines
Sun, Dec 28 - Sat, Jan 10
NAP
Naples
ORD
Chicago
$488 Roundtrip, found 2 days ago
$488
Roundtrip
found 2 days ago
Select Scandinavian Airlines flight, departing Sun, Dec 28 from Naples to Chicago, returning Sat, Jan 10, priced at $488 found 2 days ago
British Airways
Thu, Apr 16 - Mon, Apr 20
NAP
Naples
ORD
Chicago
$611 Roundtrip, found 21 hours ago
$611
Roundtrip
found 21 hours ago
Select British Airways flight, departing Thu, Apr 16 from Naples to Chicago, returning Mon, Apr 20, priced at $611 found 21 hours ago
Aer Lingus
Thu, Oct 2 - Mon, Oct 6
NAP
Naples
ORD
Chicago
$615 Roundtrip, found 5 days ago
$615
Roundtrip
found 5 days ago
Select Aer Lingus flight, departing Thu, Oct 2 from Naples to Chicago, returning Mon, Oct 6, priced at $615 found 5 days ago
Iberia
Thu, Sep 18 - Fri, Sep 26
NAP
Naples
ORD
Chicago
$641 Roundtrip, found 20 hours ago
$641
Roundtrip
found 20 hours ago
Select Iberia flight, departing Thu, Sep 18 from Naples to Chicago, returning Fri, Sep 26, priced at $641 found 20 hours ago
Air Canada
Thu, Aug 28 - Wed, Sep 3
NAP
Naples
ORD
Chicago
$654 Roundtrip, found 9 hours ago
$654
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Thu, Aug 28 from Naples to Chicago, returning Wed, Sep 3, priced at $654 found 9 hours ago
Lufthansa
Thu, Oct 2 - Wed, Oct 8
NAP
Naples
ORD
Chicago
$655 Roundtrip, found 3 days ago
$655
Roundtrip
found 3 days ago
Select Lufthansa flight, departing Thu, Oct 2 from Naples to Chicago, returning Wed, Oct 8, priced at $655 found 3 days ago
Swiss International Air Lines
Thu, Apr 16 - Mon, Apr 20
NAP
Naples
ORD
Chicago
$664 Roundtrip, found 21 hours ago
$664
Roundtrip
found 21 hours ago
Select Swiss International Air Lines flight, departing Thu, Apr 16 from Naples to Chicago, returning Mon, Apr 20, priced at $664 found 21 hours ago
ITA Airways
Wed, Aug 27 - Wed, Sep 17
NAP
Naples
ORD
Chicago
$668 Roundtrip, found 1 day ago
$668
Roundtrip
found 1 day ago
Select ITA Airways flight, departing Wed, Aug 27 from Naples to Chicago, returning Wed, Sep 17, priced at $668 found 1 day ago
Austrian Airlines
Wed, Oct 1 - Sun, Oct 5
NAP
Naples
ORD
Chicago
$675 Roundtrip, found 1 day ago
$675
Roundtrip
found 1 day ago
Select Austrian Airlines flight, departing Wed, Oct 1 from Naples to Chicago, returning Sun, Oct 5, priced at $675 found 1 day ago

Find the cheapest month to fly from Naples (NAP) to Chicago (ORD)

September is typically the cheapest month to fly

From $516 - $995 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $734
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $734
Flights from Naples (NAP) to Chicago (ORD)
Origin airport
Naples Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aer Lingus, Air Canada, Air France, American Airlines, Austrian Airlines, British Airways, Brussels Airlines, Delta, Emirates, Finnair, ITA Airways, Iberia, KLM, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$399
Distance
4932 mi
Average flight time
10 hours 50 mins

Naples to Chicago Flights

The cheapest times to fly from Naples to Chicago

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 Naples to Chicago are during the month of September. You can find some of the cheapest flights from Naples to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Naples to Chicago

Sunday is one of the best days to book for cheap flights from Naples to Chicago: 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 Naples to Chicago

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 Naples to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $604 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 Naples to Chicago 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 Naples to Chicago 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 Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD) cost?
Book cheap return tickets starting from $694 from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD). 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 NAP on July 11 2025 and touching down at ORD. The price was last updated on June 30 2025 and has not changed since.
What is the cheapest month to fly from NAP to ORD?
Look for direct flights from NAP to ORD in October to land cheaper tickets. You can find a one-way American Airlines flight for $723 leaving on October 12 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on June 30 2025 and remains unchanged.
What is the cheapest airline that flies from NAP to ORD?
Journey from NAP to ORD with American Airlines. This carrier currently offers the cheapest one-way fare for this route, starting from $726. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from NAP on September 13 2025. Prices were last updated on June 30 2025 and have not changed since.
How many flights per day from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD)?
You'll need to take a flight with a layover when traveling from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from NAP to ORD?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a range of factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) without delays, opt for a flight that leaves from Naples Intl. Airport (NAP) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from NAP to ORD right before your trip is usually more expensive. However, if you're flexible with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book a NAP to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a NAP to ORD flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place will take the stress out of planning your trip. Just pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD)?
If you reserved your NAP to ORD flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes after 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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