NAP - ORD

$383 Find Cheap Flights from Naples to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Naples to O'Hare Intl departing on 9/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Naples to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Naples to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Naples to Chicago (NAP-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Naples to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Naples to O'Hare Intl

Thu, Aug 21 - Sun, Aug 31
TAP AIR PORTUGAL Logo
7:15 pm - 4:10 pmNAP-ORD
27h 55m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 amORD-NAP
34h 40m1 stop
$407TAP AIR PORTUGAL
Find Deal
Thu, Aug 21 - Sun, Aug 31
TAP AIR PORTUGAL Logo
7:15 pm - 4:10 pmNAP-ORD
27h 55m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 amORD-NAP
34h 40m1 stop
$408TAP AIR PORTUGAL
Find Deal
Mon, Aug 25 - Tue, Sep 2
British Airways Logo
12:00 pm - 8:11 pmNAP-ORD
15h 11m1 stop
British Airways Logo
7:10 pm - 10:00 pmORD-NAP
19h 50m1 stop
$609British Airways
Find Deal
Thu, Aug 21 - Mon, Sep 1
KLM Logo
11:40 am - 2:10 pmNAP-ORD
33h 30m1 stop
KLM Logo
5:10 pm - 10:05 pmORD-NAP
21h 55m1 stop
$613KLM
Find Deal
Mon, Aug 25 - Tue, Sep 2
American Airlines Logo
3:00 pm - 6:50 pmNAP-ORD
10h 50mnonstop
American Airlines Logo
10:20 am - 10:00 amORD-NAP
16h 40m1 stop
$615American Airlines
Find Deal
Mon, Aug 25 - Tue, Sep 2
KLM Logo
6:10 am - 3:00 pmNAP-ORD
15h 50m1 stop
KLM Logo
2:00 pm - 11:35 amORD-NAP
14h 35m2 stops
$619KLM
Find Deal
Mon, Aug 25 - Tue, Sep 2
American Airlines Logo
12:00 pm - 10:49 pmNAP-ORD
17h 49m1 stop
American Airlines Logo
10:20 am - 10:00 amORD-NAP
16h 40m1 stop
$620American Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
Air Canada Logo
6:40 am - 2:55 pmNAP-ORD
15h 15m2 stops
Air Canada Logo
6:06 pm - 9:40 amORD-NAP
32h 34m2 stops
$622Air Canada
Find Deal
Thu, Oct 2 - Thu, Oct 9
British Airways Logo
12:00 pm - 3:43 pmNAP-ORD
34h 43m1 stop
British Airways Logo
5:00 pm - 10:00 pmORD-NAP
22h 00m1 stop
$644British Airways
Find Deal
Sat, Aug 23 - Sun, Aug 31
Air Canada Logo
11:35 am - 8:16 pmNAP-ORD
15h 41m1 stop
Air Canada Logo
6:06 pm - 9:40 amORD-NAP
56h 34m2 stops
$658Air Canada
Find Deal
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KAYAK's insights & trends for Naples to O'Hare Intl flights

Get data-powered insights and trends into flights from Naples to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Naples to Chicago?

The average price of all round-trip flights from Naples to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Naples to Chicago. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

Can I save money by flying with a layover from Naples to Chicago O'Hare Intl Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $747, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
High seasonJune
Cheapest flight$383
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Naples to Chicago

When to book flights from Naples to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Naples to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Naples to Chicago flights

  • What is the cheapest flight from Naples to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Naples to Chicago O'Hare Intl Airport was $383 for a one-way ticket and $407 for a round-trip.

  • Do I need a passport to fly between Naples and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Naples and on arrival in Chicago.

  • Which airlines offer Wi-Fi service onboard planes from Naples to Chicago?

    KLM, American Airlines, Air France, and Delta offer inflight Wi-Fi service on the Naples to Chicago flight route.

  • Which aircraft models fly most regularly from Naples to Chicago?

    The Boeing 787-9 Dreamliner is the aircraft model that flies most regularly on the Naples to Chicago flight route.

  • Which airline alliances offer flights from Naples to Chicago?

    oneworld is the only airline alliance operating flights between Naples and Chicago.

  • On which days can I fly direct from Naples to Chicago?

    There are nonstop flights from Naples to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Naples to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Naples to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Naples to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Naples is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Naples to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Naples with another airline. Booking your flights between Naples and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Naples to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Naples up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Naples to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $514 or less one-way and $741 or less round-trip.

Prefer to fly direct from Naples to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Naples to Chicago O'Hare Intl.
Find which airlines fly direct from Naples Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Naples to Chicago O'Hare Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to Naples

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top airline flying from Naples to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Naples to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Naples to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
7.2Comfort
8.0Crew
7.5Boarding
6.9Entertainment
6.5Food
Airline reviews

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

2.0 MediocreMitchell, Jun 2025CMH - ORD
Read more American Airlines reviews

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

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

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