CHI - NAP

$325 Find Cheap Flights from Chicago to Naples

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Naples departing on 4/26. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Naples

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Naples.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Naples.
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Everything you should know

Cheapest round-trip
$641
Typical prices: $872-$634
Turkish Airlines
Tue 4/21Tue 4/28
ORD - NAP • 1 stop
Cheapest non-stop
$1,000
Finnair
Thu 5/7Wed 5/20
ORD - NAP • Non-stop
Top airlines
Cheapest • from $641 (round-trip)
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines. Average duration is 9h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 68% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $531 (round-trip)
Shortest trip • 11h 45m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Naples (CHI-NAP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Naples 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 Chicago to Naples

Tue, Apr 21 - Tue, Apr 28
Turkish Airlines Logo
8:10 pm - 8:30 am
ORD
-
NAP
29h 20m
1 stop
Turkish Airlines Logo
8:45 pm - 9:40 am
NAP
-
ORD
19h 55m
1 stop
$641Turkish Airlines
Fri, Oct 2 - Wed, Oct 28
Turkish Airlines Logo
8:10 pm - 7:45 pm
ORD
-
NAP
16h 35m
1 stop
Turkish Airlines Logo
7:25 pm - 11:05 am
NAP
-
ORD
21h 40m
1 stop
$642Turkish Airlines
Sun, Sep 6 - Tue, Sep 15
Turkish Airlines Logo
8:10 pm - 7:45 pm
ORD
-
NAP
16h 35m
1 stop
Turkish Airlines Logo
9:30 am - 9:40 am
NAP
-
ORD
31h 10m
1 stop
$643Turkish Airlines
Sun, Apr 19 - Sun, May 3
Turkish Airlines Logo
8:10 pm - 7:45 pm
ORD
-
NAP
16h 35m
1 stop
Turkish Airlines Logo
9:30 am - 9:40 am
NAP
-
ORD
31h 10m
1 stop
$647Turkish Airlines
Thu, Apr 23 - Sun, Apr 26
Turkish Airlines Logo
8:10 pm - 7:45 pm
ORD
-
NAP
16h 35m
1 stop
Turkish Airlines Logo
3:45 pm - 9:40 am
NAP
-
ORD
24h 55m
1 stop
$659Turkish Airlines
Wed, Apr 29 - Thu, May 14
Scandinavian Airlines Logo
7:15 pm - 6:45 pm
ORD
-
NAP
16h 30m
1 stop
Scandinavian Airlines Logo
7:35 pm - 4:10 pm
NAP
-
ORD
27h 35m
1 stop
$674Scandinavian Airlines
Wed, Aug 12 - Fri, Aug 21
Delta Logo
5:59 pm - 6:15 pm
MDW
-
NAP
17h 16m
2 stops
Delta Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$768Delta
Wed, Aug 12 - Fri, Aug 21
Delta Logo
9:30 am - 11:30 am
MDW
-
NAP
19h 00m
2 stops
Delta Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$769Delta
Wed, Aug 12 - Fri, Aug 21
KLM Logo
5:25 pm - 7:05 am
MDW
-
NAP
30h 40m
1 stop
KLM Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$821KLM
Wed, Aug 12 - Fri, Aug 21
KLM Logo
5:25 pm - 7:05 am
MDW
-
NAP
30h 40m
1 stop
KLM Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$871KLM
Booking Insights

KAYAK's insights & trends for Chicago to Naples flights

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

How much is a round-trip flight from Chicago to Naples?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Naples departing in April.

What is the cheapest Chicago to Naples flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Naples costs $649 on the route between Chicago O'Hare Intl Airport (ORD) and Naples (NAP). It is also the most popular route.

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

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

If you are looking for a flight deal from Chicago to Naples, look for departures on Tuesdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Naples, Saturday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Chicago to Naples?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Naples, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Naples is February, where tickets cost $540 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $1,146 and $995 respectively.

Can I save money by flying with a layover from Chicago to Naples?

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 $692, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Naples?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Naples, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Naples, you should book around 5 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$325
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago O'Hare Airport to Naples

When to book flights from Chicago to Naples

Are your dates flexible? Find out the best times to travel from Chicago to Naples 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 flights from Chicago to Naples

  • How many flights are there between Chicago and Naples per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Naples, with an average flight time of 9h 35m. The most common departure time is 5:00 pm and most flights take off in the afternoon. Each week, there are 6 flights.

  • What is the cheapest flight from Chicago to Naples?

    In the last 3 days, the lowest price for a flight from Chicago to Naples was $325 for a one-way ticket and $641 for a round-trip.

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

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

  • Which airports will I be using when flying from Chicago to Naples?

    Chicago is served by 2 major airports and there is only 1 main airport in Naples. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Naples.

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

    American Airlines, Finnair, British Airways, and Iberia offer inflight Wi-Fi service on the Chicago to Naples flight route.

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

    The Boeing 787-8 Dreamliner is the aircraft model that flies most regularly on the Chicago to Naples flight route.

  • Which airline alliances offer flights from Chicago to Naples?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Naples, with SkyTeam being the most commonly used for this route.

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

    You can catch a nonstop flight from Chicago to Naples on on Monday, Tuesday, Wednesday, Thursday, Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to Naples, SWISS or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Naples are SWISS and United Airlines. With an average price for the route of $882 and an overall rating of 7.5, SWISS is the most popular choice. United Airlines is also a great choice for the route, with an average price of $982 and an overall rating of 7.4.

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

    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 Chicago to Naples.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Naples from Chicago 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 Chicago to Naples?

    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 Naples with an airline and back to Chicago with another airline.

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

    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 Naples from Chicago 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 Chicago to Naples

  • Looking for a cheap flight? 25% of our users found flights on this route for $722 or less one-way and $934 or less round-trip.

Prefer to fly direct from Chicago to Naples?

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

Direct departures

Chicago 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

Direct returns

Naples to Chicago

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 5 airlines serving from Chicago to Naples

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Naples. 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 Chicago to Naples? 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.
7.5
SWISSOverall score based on 1916 reviews
8.3Crew
7.1Food
6.8Entertainment
7.4Comfort
7.7Boarding
Airline reviews

The flight itself was fine, but due to a snow delay my connection to Lisbon was delayed by six hours. Despite this, Swiss Air still managed to lose my luggage. Not acceptable. Someone else on the flight also lost their luggage.

6.0 GoodSonja, Jan 2026
BOS - ZRH
Read more SWISS reviews

The flight itself was fine, but due to a snow delay my connection to Lisbon was delayed by six hours. Despite this, Swiss Air still managed to lose my luggage. Not acceptable. Someone else on the flight also lost their luggage.

Bad experience overall. Crew did not provide food for our 2 year old (even though we specifically bought a child infant seat for her and literally bought another full price flight), which was unacceptable. And we had to pay $310 each way to carry our ski equipment even though they advertise it as something that is free. Tickets were purchased the same way as usual, but they told us we had Economy Light tickets (I never elected to have such seats). Just plain manipulation and false advertisment. Very disappointed overall about this airline.

The trip was great until my luggage was lost on transfer from United to Swiss. It took Swiss 3 days to get my luggage to me though it was located almost immediately.

It was much better than most airlines we have flown with. It remo des me Swiss Air 25 years ago.

Made us gate check carry ons Then didn’t get them on the plane. Service they used didn’t deliver our carry ons for more than a day Total mess

Horrible!! The WiFi was not working, the food was awful

We’ve never been more uncomfortable on a flight than we have on this particular one. The seats in front of us reclined so far back that when the person reclined their seat of broccoli, it almost hit me in the face and left me with literally no room to move that said I had to recline my seed in which made the person behind me upset. It seemed like the seats also would recline without even pressing the button in the armrest and would unrecline as well for that same reason, and it also seemed that some seats reclined more than others. The bottom cushions of the seat were so thin that even after one hour of an 11 hour flight, our tailbones were so sore. It seemed like an overall old airplane. It also didn’t have individual air vents and it was extremely hot the entire flight. Several passengers were commenting on how hot it was. The breakfast was some kind of flavorless triangle, puffy egg, laying in a watery bed of steamed peppers and onions and spinach. It was not appetizing at all. The flight crew was extremely nice so that was a nice thing this flight attendant. They let us try different types of Swiss sodas, which was really nice and the dinner was actually delicious but still overall given the other considerations. It was pretty much a miserable flight without basic seat comfort.

Best international flight I have had in a while! Far superior accommodation, services, food and general experience compared to U.S. airline companies.

As an ex airline employee in my home country of Jamaica, it was wonderful to see that Swiss Air has maintained it's exemplary service. The crew was both pleasant and professional. The meals were wholesome and tasty. My brother and I traveled and we both agree that our amazing vacation started with the excellent experience with Swiss Air. Continue to keep your standards high 🙂

Food used to be better and comfort was not attainable after 5 hours everything starts hurting.

The seats seems abit small and the reclining is too much, the seat in front of me came back too much and made it uncomfortable for me.

As a first time flyer with Turkish Airlines. My experience was very good due to the factor that there were to many passengers on the my first flight compared to my connecting flight. However, I know that nothing is perfect and all companies are trying to accommodate their passengers to the best way possible. I will always say, a FEW INCHES will go LONG WAY. That's something all airliners should consider, and not only the money aspect!!! A long time commitment is better than one time service! Thank you

Flight was delayed. While standing at the gate, a note appeared on the sign saying the gate had changed to a gate far away. No member of the Turkish airlines team got on the microphone to instruct passengers to go to the other gate, to ignore the chiron, etc. Finally, the message disappeared. Eventually, the flight began to board. Very slowly. More slowly than I experience with other airlines. Though Istanbul may just be slow . . . In all other ways, great flight, great entertainment (top notch movies), great service, excellent food, comfortable lie-flat seat, dimmed lights, etc.

Staff at the airport wasn't helpful or friendly. Probably the worst airport experience I have ever had, going and coming. The staff on the plane was better. Still not super friendly or personable. However, they were not rude like airport staff. They ran out of certain menu items. Maybe could have been prepared better? Overall just ok.

It was a pleasant experience. In flight entertainment could have been better

The desk crew at the LAX crew could do better. A girl named Mahesi was very abrasive and unfriendly. She needs a better customer service uproar.

It was peaceful excited We enjoyed it always Turkish peaceful excited

Istanbul to Lahore flight was less than standard for international business class cabins. Seat did not were not flat and it did not operate easily. I had to push buttons hard repeatedly to operate the seat. I was in 5A seat

IAH to Istanbul was outstanding across the board. The flight from Istanbul to Male was good, not great.

the cabin was kept too hot. couldn't sleep as a result

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

In general, I've had excellent experiences with Iberia flights and will continue to use them. In this last flight there were two things that didn't go right. I didn't get the kosher meal I had pre-requested when I had checked in on-line. Things worked out OK as we ended up eating the fish and vegetarian choices, which were really good. The other issue was that some movies for me and my wife started fine but after 8-12 minutes the content just switched to something else. The flight attendant reset our entertainment systems, but the problem persisted. We ended up choosing other movies/TV shows that did work fine.

Awful. They didn't even show concern that her connecting flight( Dallas to Mardrid) was gone/missing. I don't understand how that is even possible. Rudest answer from one of the crew was that American Airlines sold the tickets to somebody else. My daughter was not in the list.

The flight was canceled on a Thursday last minute. I lost thousands of dollars in hotels and car rental

Excellent lie flat seat for premium economy! Great staff. Bad food . Not so great entertainment. My bag didn’t make it either.

Really like the idea experience on this airline I will use again

30 minutes still don't have gate number, ask many people can't get answer.

Plane delayed due to weather. Plane boarded, then told to unboard due to a maintenance issue.

the seats were so cramped you could barely move. it was difficult to eat when passengers would recline their seats. the seats were so flimsy and unstable that whenever someone got in and out of their seat, it bounced like a spring back in your face. the movies were nice. the food was terrible. even though the conditions were terrible, they tried to pressure passengers to relocate their seats to accommodate adults who were related and wanted to sit next to each other, even after the passengers expressed that they did not want to move for that purpose. on the connecting flight, the “service” consisted of items for purchase. even though the flight was only 45 minutes, once again passengers (including me) were pressured to relocate for people to sit next to each other. they couldn’t be apart for 45 minutes? this was much less compelling than being apart for an 8 hour flight.

Everything went smoothly, and we even arrived 40min earlier than scheduled, on an Orland-Madrid route.

The staff was very nice and helpful. Some of the best crew I have met.

The gate agent made me check my carry-on in Denver, even though I've traveled all over taking this case on the plane. Beware folks. Food in Premium Economy was quite good - excellent blanket! Flight attendants on the Heathrow-to-Budapest flight on 3-27-2026 were quite snappy. I got a frown when asked to unscrew the water bottle cap for me (I had a cast on my right arm). Also woke up right when they were handing out biscuits. She had given my rowmates one and was in the process of giving water when I asked for a biscuit. She scolded me and said, "You snooze, you lose". She did give me one, but I thought that comment was uncalled for.

Wish the food and overall service was better. They treat Business class passengers same as economy

WiFi wasn’t available to economy until the end of the flight.

Very good staff members with sincere passion and responsibility in their job.

We paid for Business Class seats, but system did not have us and they were not available.

Very please with the seating that the Kayak staff booked for us!

Worth every penny to upgrade to BC. Treated and felt more like First Class

It is an airline that has the service that used to be in the old times as a standard and now is rare. Very good.

I was unable to board this flight because of visa changes that I was not alerted about and I’ve been unable to contact Kayak to obtain a refund / credit anything.

Boarding was efficient and quick, crew was very attentive, seats were comfortable.

Everything you need to know for your flight from Chicago to Naples

Information on your arrival and departure airports