$476 Cheap Flights from Naples (NAP) to Chicago (ORD)

View $476 flight on Thu, Jun 5, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Naples to Chicago (NAP-ORD)

Prices were available within the past 7 days and start at $476 for one-way flights and $524 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Sat, Aug 23 - Fri, Sep 5
NAP
Naples
ORD
Chicago
$524 Roundtrip, found 7 hours ago
$524
Roundtrip
found 7 hours ago
Select Scandinavian Airlines flight, departing Sat, Aug 23 from Naples to Chicago, returning Fri, Sep 5, priced at $524 found 7 hours ago
Iberia
Sun, Sep 21 - Fri, Oct 3
NAP
Naples
ORD
Chicago
$579 Roundtrip, found 1 day ago
$579
Roundtrip
found 1 day ago
Select Iberia flight, departing Sun, Sep 21 from Naples to Chicago, returning Fri, Oct 3, priced at $579 found 1 day ago
Aer Lingus
Thu, May 8 - Mon, May 12
NAP
Naples
ORD
Chicago
$645 Roundtrip, found 1 day ago
$645
Roundtrip
found 1 day ago
Select Aer Lingus flight, departing Thu, May 8 from Naples to Chicago, returning Mon, May 12, priced at $645 found 1 day ago
Swiss International Air Lines
Wed, Oct 22 - Wed, Nov 12
NAP
Naples
ORD
Chicago
$647 Roundtrip, found 3 days ago
$647
Roundtrip
found 3 days ago
Select Swiss International Air Lines flight, departing Wed, Oct 22 from Naples to Chicago, returning Wed, Nov 12, priced at $647 found 3 days ago
ITA Airways
Sun, Sep 7 - Wed, Sep 24
NAP
Naples
ORD
Chicago
$651 Roundtrip, found 3 days ago
$651
Roundtrip
found 3 days ago
Select ITA Airways flight, departing Sun, Sep 7 from Naples to Chicago, returning Wed, Sep 24, priced at $651 found 3 days ago
Lufthansa
Sat, Sep 13 - Wed, Oct 1
NAP
Naples
ORD
Chicago
$655 Roundtrip, just found
$655
Roundtrip
just found
Select Lufthansa flight, departing Sat, Sep 13 from Naples to Chicago, returning Wed, Oct 1, priced at $655 just found
American Airlines
Wed, May 7 - Sun, May 18
NAP
Naples
ORD
Chicago
$661 Roundtrip, found 5 days ago
$661
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, May 7 from Naples to Chicago, returning Sun, May 18, priced at $661 found 5 days ago
United
Sat, May 17 - Wed, May 28
NAP
Naples
ORD
Chicago
$662 Roundtrip, found 8 hours ago
$662
Roundtrip
found 8 hours ago
Select United flight, departing Sat, May 17 from Naples to Chicago, returning Wed, May 28, priced at $662 found 8 hours ago
Air Canada
Fri, May 23 - Fri, May 30
NAP
Naples
ORD
Chicago
$663 Roundtrip, found 16 hours ago
$663
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Fri, May 23 from Naples to Chicago, returning Fri, May 30, priced at $663 found 16 hours ago
Austrian Airlines
Thu, May 8 - Mon, May 12
NAP
Naples
ORD
Chicago
$665 Roundtrip, found 1 day ago
$665
Roundtrip
found 1 day ago
Select Austrian Airlines flight, departing Thu, May 8 from Naples to Chicago, returning Mon, May 12, priced at $665 found 1 day ago
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, Icelandair, KLM, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$523
Distance
4932 mi

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 August. 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 $476 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 $763 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 May 17 2025 and touching down at ORD. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from NAP to ORD?
The cheapest flights from NAP to ORD 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 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 $710. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from NAP on May 23 2025. Prices were last updated on April 24 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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*Available to One Key members.