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 $398 for one-way flights and $487 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Fri, Apr 24 - Fri, May 1
NAP
Naples
ORD
Chicago
$487 Roundtrip, found 4 days ago
$487
Roundtrip
found 4 days ago
Select TAP Portugal flight, departing Fri, Apr 24 from Naples to Chicago, returning Fri, May 1, priced at $487 found 4 days ago
Scandinavian Airlines
Thu, Mar 5 - Wed, Mar 11
NAP
Naples
ORD
Chicago
$567 Roundtrip, found 1 day ago
$567
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Thu, Mar 5 from Naples to Chicago, returning Wed, Mar 11, priced at $567 found 1 day ago
Scandinavian Airlines
Sat, Nov 8 - Sat, Nov 29
NAP
Naples
ORD
Chicago
$587 Roundtrip, found 5 days ago
$587
Roundtrip
found 5 days ago
Select Scandinavian Airlines flight, departing Sat, Nov 8 from Naples to Chicago, returning Sat, Nov 29, priced at $587 found 5 days ago
Delta
Sat, Feb 28 - Sun, Mar 1
NAP
Naples
ORD
Chicago
$621 Roundtrip, found 1 day ago
$621
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Feb 28 from Naples to Chicago, returning Sun, Mar 1, priced at $621 found 1 day ago
Lufthansa
Mon, Nov 24 - Sun, Nov 30
NAP
Naples
ORD
Chicago
$624 Roundtrip, found 6 days ago
$624
Roundtrip
found 6 days ago
Select Lufthansa flight, departing Mon, Nov 24 from Naples to Chicago, returning Sun, Nov 30, priced at $624 found 6 days ago
Swiss International Air Lines
Thu, Nov 20 - Wed, Nov 26
NAP
Naples
ORD
Chicago
$628 Roundtrip, found 10 hours ago
$628
Roundtrip
found 10 hours ago
Select Swiss International Air Lines flight, departing Thu, Nov 20 from Naples to Chicago, returning Wed, Nov 26, priced at $628 found 10 hours ago
Austrian Airlines
Fri, Nov 7 - Tue, Nov 11
NAP
Naples
ORD
Chicago
$647 Roundtrip, found 5 days ago
$647
Roundtrip
found 5 days ago
Select Austrian Airlines flight, departing Fri, Nov 7 from Naples to Chicago, returning Tue, Nov 11, priced at $647 found 5 days ago
Iberia
Tue, Jan 27 - Mon, Feb 2
NAP
Naples
ORD
Chicago
$654 Roundtrip, found 7 hours ago
$654
Roundtrip
found 7 hours ago
Select Iberia flight, departing Tue, Jan 27 from Naples to Chicago, returning Mon, Feb 2, priced at $654 found 7 hours ago
British Airways
Thu, Apr 23 - Sat, May 2
NAP
Naples
ORD
Chicago
$655 Roundtrip, found 6 hours ago
$655
Roundtrip
found 6 hours ago
Select British Airways flight, departing Thu, Apr 23 from Naples to Chicago, returning Sat, May 2, priced at $655 found 6 hours ago
ITA Airways
Wed, Sep 2 - Thu, Sep 17
NAP
Naples
ORD
Chicago
$662 Roundtrip, found 2 days ago
$662
Roundtrip
found 2 days ago
Select ITA Airways flight, departing Wed, Sep 2 from Naples to Chicago, returning Thu, Sep 17, priced at $662 found 2 days 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 $971
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $971

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 $398 or cheap return flight from $487 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.

Book with confidence

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 $398 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.

 

Naples to Chicago Flights

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