ORD - APF

Find cheap flights from Chicago to Naples

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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, 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 Chicago to Naples, as well as popular online travel agencies
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Cheap Flights from Chicago to Naples

 
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.

Recent round-trip flight deals from Chicago to Naples

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Naples.
Discover the best prices for you by selecting your travel dates on KAYAK.
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ORD-APF
1147 mimulti-stop
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APF-ORD
1147 mimulti-stop
Multiple Airlines
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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.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Naples?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Naples is January, where tickets cost $58 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $602 and $541 respectively.

Good to know

Low season

October

High season

February
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 37% lower on average.

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 Chicago to Naples flights

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

    No, a passport isn't needed to fly from Chicago to Naples. However, local authorities might ask for an official ID.

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

    We unfortunately don’t have that data for this specific route.

  • 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. Booking your flights between Chicago and APF 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 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.

See more FAQs

Top airlines flying 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.
7.4
United AirlinesOverall score based on 8685 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

10.0 ExcellentDr. Joseph, Apr 2025ORD - IAH
Read more United Airlines reviews

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Perfect for the money paid. Flight from Indianapolis to Fort Lauderdale. Very courteous airport staff and crew. The boarding process went very smooth. Indianapolis was in the middle of several sever storms, delaying boarding and they found a window between the storms, asked everyone for a quick boarding and we departed before we would be held longer by the next storm front. A little rough air 20 min or so after take off, however I’ll take that to being grounded the whole night. Seats kind of small, kind of hard, but very doable for the 2.5 hrs flight. Snacks and drinks available for purchase. We didn’t, as it was a late night flight. One of the checked luggage came wet in Florida and clothes inside got wet from the water that infiltrated through the zipper, I’m assuming it was in the rain in Indianapolis, I cannot blame Spirit as I think the baggage handlers are hired by the airport. I’ll be more careful next time, as I have suitcases that are more water proof and maybe I should only purchase that kind.

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

The flight was on time. The seats are very narrow.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

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

Information on your arrival and departure airports

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