$403 Cheap Flights from Naples (NAP) to Chicago (ORD)

View $403 flight on Thu, Apr 23, 2026Opens 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 $403 for one-way flights and $483 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Thu, Apr 16 - Sat, May 2
NAP
Naples
ORD
Chicago
$483 Roundtrip, found 1 day ago
$483
Roundtrip
found 1 day ago
Select TAP Portugal flight, departing Thu, Apr 16 from Naples to Chicago, returning Sat, May 2, priced at $483 found 1 day ago
British Airways
Tue, Apr 28 - Sat, May 9
NAP
Naples
ORD
Chicago
$558 Roundtrip, found 6 days ago
$558
Roundtrip
found 6 days ago
Select British Airways flight, departing Tue, Apr 28 from Naples to Chicago, returning Sat, May 9, priced at $558 found 6 days ago
Lufthansa
Wed, Oct 22 - Sun, Oct 26
NAP
Naples
ORD
Chicago
$562 Roundtrip, found 5 days ago
$562
Roundtrip
found 5 days ago
Select Lufthansa flight, departing Wed, Oct 22 from Naples to Chicago, returning Sun, Oct 26, priced at $562 found 5 days ago
Air Canada
Wed, Oct 22 - Mon, Nov 3
NAP
Naples
ORD
Chicago
$568 Roundtrip, found 5 days ago
$568
Roundtrip
found 5 days ago
Select Air Canada flight, departing Wed, Oct 22 from Naples to Chicago, returning Mon, Nov 3, priced at $568 found 5 days ago
Swiss International Air Lines
Wed, Oct 22 - Sun, Oct 26
NAP
Naples
ORD
Chicago
$569 Roundtrip, found 5 days ago
$569
Roundtrip
found 5 days ago
Select Swiss International Air Lines flight, departing Wed, Oct 22 from Naples to Chicago, returning Sun, Oct 26, priced at $569 found 5 days ago
Scandinavian Airlines
Thu, Dec 4 - Wed, Dec 10
NAP
Naples
ORD
Chicago
$577 Roundtrip, found 4 days ago
$577
Roundtrip
found 4 days ago
Select Scandinavian Airlines flight, departing Thu, Dec 4 from Naples to Chicago, returning Wed, Dec 10, priced at $577 found 4 days ago
Austrian Airlines
Thu, Oct 16 - Mon, Oct 20
NAP
Naples
ORD
Chicago
$580 Roundtrip, found 2 days ago
$580
Roundtrip
found 2 days ago
Select Austrian Airlines flight, departing Thu, Oct 16 from Naples to Chicago, returning Mon, Oct 20, priced at $580 found 2 days ago
Delta
Sat, Jan 24 - Sun, Jan 25
NAP
Naples
ORD
Chicago
$628 Roundtrip, found 6 days ago
$628
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jan 24 from Naples to Chicago, returning Sun, Jan 25, priced at $628 found 6 days ago
Brussels Airlines
Thu, Nov 20 - Wed, Nov 26
NAP
Naples
ORD
Chicago
$647 Roundtrip, found 3 days ago
$647
Roundtrip
found 3 days ago
Select Brussels Airlines flight, departing Thu, Nov 20 from Naples to Chicago, returning Wed, Nov 26, priced at $647 found 3 days ago
ITA Airways
Sun, Mar 29 - Wed, Apr 15
NAP
Naples
ORD
Chicago
$668 Roundtrip, found 1 day ago
$668
Roundtrip
found 1 day ago
Select ITA Airways flight, departing Sun, Mar 29 from Naples to Chicago, returning Wed, Apr 15, priced at $668 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 $404 - $934 per traveler.

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 $774
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $774
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, Finnair, ITA Airways, Iberia, KLM, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$483
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 April. 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 $403 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?
Snag a cheap one-way flight from $403 or cheap return flight from $483 from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD)?
Flying in April is a great way to save, as it's the cheapest month for flights between NAP and ORD. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Naples Intl. Airport (NAP) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest NAP to ORD flight.
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.