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$505 Cheap Flights from Naples (NAP) to Chicago (ORD)

View $505 flight on Wed, Feb 3, 2027Opens 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 $505 for one-way flights and $543 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, Apr 10 - Sun, Apr 11
NAP
Naples
ORD
Chicago
$543 Roundtrip, found 9 hours ago
$543
Roundtrip
found 9 hours ago
Select United flight, departing Sat, Apr 10 from Naples to Chicago, returning Sun, Apr 11, priced at $543 found 9 hours ago
Finnair
Sat, Oct 3 - Thu, Oct 8
NAP
Naples
ORD
Chicago
$635 Roundtrip, found 3 days ago
$635
Roundtrip
found 3 days ago
Select Finnair flight, departing Sat, Oct 3 from Naples to Chicago, returning Thu, Oct 8, priced at $635 found 3 days ago
British Airways
Sat, Oct 3 - Thu, Oct 8
NAP
Naples
ORD
Chicago
$640 Roundtrip, found 3 days ago
$640
Roundtrip
found 3 days ago
Select British Airways flight, departing Sat, Oct 3 from Naples to Chicago, returning Thu, Oct 8, priced at $640 found 3 days ago
Iberia
Sun, Oct 4 - Sat, Oct 10
NAP
Naples
ORD
Chicago
$646 Roundtrip, found 3 days ago
$646
Roundtrip
found 3 days ago
Select Iberia flight, departing Sun, Oct 4 from Naples to Chicago, returning Sat, Oct 10, priced at $646 found 3 days ago
ITA Airways
Thu, May 20 - Thu, Jun 3
NAP
Naples
ORD
Chicago
$657 Roundtrip, found 9 hours ago
$657
Roundtrip
found 9 hours ago
Select ITA Airways flight, departing Thu, May 20 from Naples to Chicago, returning Thu, Jun 3, priced at $657 found 9 hours ago
Swiss International Air Lines
Sat, Apr 10 - Sun, Apr 11
NAP
Naples
ORD
Chicago
$690 Roundtrip, found 9 hours ago
$690
Roundtrip
found 9 hours ago
Select Swiss International Air Lines flight, departing Sat, Apr 10 from Naples to Chicago, returning Sun, Apr 11, priced at $690 found 9 hours ago
Lufthansa
Sat, Apr 3 - Tue, Apr 13
NAP
Naples
ORD
Chicago
$692 Roundtrip, found 4 hours ago
$692
Roundtrip
found 4 hours ago
Select Lufthansa flight, departing Sat, Apr 3 from Naples to Chicago, returning Tue, Apr 13, priced at $692 found 4 hours ago
Scandinavian Airlines
Sat, Apr 10 - Sun, Apr 11
NAP
Naples
ORD
Chicago
$694 Roundtrip, found 9 hours ago
$694
Roundtrip
found 9 hours ago
Select Scandinavian Airlines flight, departing Sat, Apr 10 from Naples to Chicago, returning Sun, Apr 11, priced at $694 found 9 hours ago
Air Canada
Sat, Apr 3 - Tue, Apr 13
NAP
Naples
ORD
Chicago
$704 Roundtrip, found 4 hours ago
$704
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Sat, Apr 3 from Naples to Chicago, returning Tue, Apr 13, priced at $704 found 4 hours ago
Turkish Airlines
Mon, Jan 25 - Mon, Feb 8
NAP
Naples
ORD
Chicago
$773 Roundtrip, found 2 days ago
$773
Roundtrip
found 2 days ago
Select Turkish Airlines flight, departing Mon, Jan 25 from Naples to Chicago, returning Mon, Feb 8, priced at $773 found 2 days ago

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 $1,246
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $1,246

What you need to know for your flight from Naples Intl. to O'Hare Intl.

Naples (NAP) to Chicago (ORD) at a glance

Travel with a range of airlines offering flights from Naples (NAP) to Chicago (ORD) on this international long-haul journey. Review the options from full-service carriers to discover the itinerary that aligns with your budget, schedule, and travel plans while you uncover the iconic sights and neighborhoods of Chicago. Gather essential information for your flights departing from Naples International Airport (NAP) to O'Hare International Airport (ORD).

  • Fastest flight duration: around 10h 45m non-stop
  • Route distance: roughly 4,900 miles (7,890 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $365–$1240, depending on seasonality and how far ahead you book

Flights from Naples International Airport (NAP) to O'Hare International Airport (ORD)

Based on recent traveler bookings, here are the top airlines preferred for flights from Naples to Chicago, featuring both non-stop and one-stop options. Popular layover airports include Istanbul Airport (IST) with about a 2-hour connection, Dublin Airport (DUB) at approximately 2 hours and 30 minutes, and Adolfo Suárez Madrid-Barajas Airport (MAD), also around 2 hours and 30 minutes. This flexibility allows you to compare prices, total travel times, and cabin classes to find the ideal itinerary for your journey.

  • American Airlines: As a comprehensive service airline, American Airlines provides both non-stop and one-stop flights. One-way ticket prices generally range from $370 to $1375. This carrier represents about 42% of departures for this route, with a direct flight time averaging 10 hours and 45 minutes.
  • Turkish Airlines: This full-service airline offers one-stop options, with one-way fares typically between $515 and $1190. It accounts for around 30% of departures on this route, featuring an in-flight duration of 13 hours and 30 minutes, totaling approximately 15 hours and 30 minutes when including layovers.
  • Aer Lingus: Providing one-stop service, Aer Lingus is a full-service airline with one-way fares ranging from $445 to $1065. It makes up about 8% of the departures on this route, with an in-flight time of 13 hours and 30 minutes and a total journey time of around 15 hours and 30 minutes, considering layovers.
  • British Airways: This full-service carrier offers one-stop flights with one-way fares generally between $365 and $735. Representing roughly 6% of departures on this route, British Airways features an in-flight duration of 13 hours and 30 minutes, leading to a total travel time of about 15 hours and 30 minutes, including layovers.
  • ITA Airways: A full-service airline, ITA Airways provides one-stop service with one-way fares typically ranging from $770 to $1330. It covers around 4% of departures on this route and has an in-flight time of 13 hours and 30 minutes, resulting in a total journey time of approximately 21 hours and 45 minutes when factoring in layovers.

Alternative routes from Naples (NAP) to Chicago (ORD)

  • Naples to Chicago (NAP-MDW): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD).
  • Salerno to Chicago (QSR-ORD): Costa d'Amalfi Airport (QSR) lies about 37 miles from Naples International Airport (NAP).

How to find the best prices for flights from Naples (NAP) to Chicago (ORD)

Getting some of the best deals on flights from Naples to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, although most travelers tend to book at least 2 months ahead. Morning departures (5 am-12 pm) often offer lower prices, while afternoon flights (12 pm-6 pm) are more popular. Additionally, flying on Saturday provides both cheaper rates and is the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Naples International Airport

Chicago welcomes travelers from Naples with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is approximately 2.2 miles away by car, providing convenient transport options for travelers.

Frequently asked questions

How much does a flight from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $505 and cheap return flights from $543 Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $646 and $4476, and return flights often range between $814 and $6269. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from NAP to ORD is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
American Airlines offers around 7 weekly direct flights from NAP to ORD.
How do I find cheap flights from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Naples (NAP) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. Lufthansa offers the most daily flights from NAP to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 1 nonstop flights per day from Naples Intl. (NAP) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Naples (NAP) to Chicago, IL (ORD) usually departs at around 6:00 AM local time, operated by Lufthansa and Air Canada. This seasonal service is active in June and August, giving you a head start on your travels to the Windy City. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from Naples (NAP) to Chicago, IL (ORD), the most popular departure times are in the early morning, from 6am to 9am. This time window accounts for about 34% of total traffic. Many major carriers, including Iberia and Lufthansa, offer flights during this window. This timing is favored as it allows travelers to arrive in Chicago with plenty of time to explore the city.
How long does it take to fly from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from NAP to ORD takes around 10 hours 50 minutes, with the route covering approximately 4,933 miles. Flights with a layover typically take 4 hours 40 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Business class is available on flights from NAP to ORD. Airlines that offer business class service on this route include:

  • Swiss International Air Lines
  • ITA Airways
  • Lufthansa
  • Iberia
  • Turkish Airlines
  • Finnair
  • American Airlines
  • Air France
  • British Airways
  • flydubai

How much is a business class flight from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A non-stop, one-way business class flight from Naples (NAP) to Chicago, IL (ORD) is usually around $4,239. there is no data available for round-trip prices. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Naples Intl. (NAP)?
If you're planning to travel to Chicago from Naples Intl. (NAP), you can fly into O'Hare Intl. (ORD) Some flights may connect through major hubs like Fiumicino - Leonardo da Vinci Intl. (FCO), Franz Josef Strauss Intl. (MUC), Frankfurt Intl. (FRA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Naples (NAP-Naples Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

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, Icelandair, KLM, LOT-Polish Airlines, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$543
Distance
4932 mi
Average flight time
10 hours 55 mins

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 2026. You can also book with separate airlines for your outbound and return journeys, from $505 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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