NAP - ORD

$321 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 10/9. 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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Flight 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Wed, Sep 17 - Sun, Sep 21
SWISS Logo
2:50 pm - 3:55 pmNAP-ORD
32h 05m1 stop
SWISS Logo
9:50 pm - 8:45 amORD-NAP
27h 55m2 stops
$540SWISS
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Wed, Sep 17 - Sun, Sep 21
United Airlines Logo
11:35 am - 8:11 pmNAP-ORD
15h 36m1 stop
United Airlines Logo
6:00 am - 11:40 amORD-NAP
22h 40m1 stop
$541United Airlines
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Wed, Sep 17 - Sun, Sep 21
American Airlines Logo
3:00 pm - 6:50 pmNAP-ORD
10h 50mnonstop
American Airlines Logo
8:40 pm - 10:00 pmORD-NAP
18h 20m1 stop
$547American Airlines
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Mon, Oct 20 - Wed, Jan 14
British Airways Logo
12:00 pm - 8:11 pmNAP-ORD
15h 11m1 stop
British Airways Logo
9:40 am - 11:45 amORD-NAP
19h 05m2 stops
$550British Airways
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Thu, Oct 2 - Mon, Oct 6
Logo
7:40 am - 6:50 pmNAP-ORD
18h 10m2 stops
Logo
2:41 pm - 10:00 amORD-NAP
12h 19m1 stop
$553
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Thu, Oct 2 - Mon, Oct 6
British Airways Logo
7:40 am - 6:15 pmNAP-ORD
17h 35m1 stop
British Airways Logo
7:15 pm - 10:00 pmORD-NAP
19h 45m1 stop
$556British Airways
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Thu, Oct 2 - Mon, Oct 6
Logo
6:50 am - 2:15 pmNAP-ORD
14h 25m1 stop
Logo
7:15 pm - 2:25 pmORD-NAP
12h 10m1 stop
$558
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Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
3:00 pm - 6:50 pmNAP-ORD
10h 50mnonstop
American Airlines Logo
4:45 pm - 10:00 amORD-NAP
34h 15m1 stop
$566American Airlines
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Thu, Oct 2 - Mon, Oct 6
Delta Logo
6:10 am - 6:04 pmNAP-ORD
18h 54m2 stops
Delta Logo
6:20 pm - 6:15 pmORD-NAP
16h 55m2 stops
$573Delta
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Thu, Oct 2 - Mon, Oct 6
Delta Logo
6:10 am - 5:45 pmNAP-ORD
18h 35m2 stops
Delta Logo
11:02 am - 11:35 amORD-NAP
17h 33m2 stops
$575Delta
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Booking Insights

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 $718, prices are generally cheapest when you fly direct.

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Good to know

Low seasonFebruary
Cheapest flight$321
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 $321 for a one-way ticket and $540 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 $692 or less one-way and $694 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
7.5Boarding
8.0Crew
7.2Comfort
6.9Entertainment
6.5Food
Airline reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

6.0 GoodMitchell, Aug 2025CMH - ORD
Read more American Airlines reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

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

Information on your arrival and departure airports

Naples (NAP)
O'Hare Intl (ORD)

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