Cheap flights from Chicago to Naples from $293
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Naples departing on 9/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Naples
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Naples?
What is the cheapest month to fly to Naples?
The cheapest month to fly to Naples from Chicago is in January. Flight prices, which tend to average around $664, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Naples from Chicago during March instead. Flights to Naples in March, while not as cheap as those in January, still average around $674.
What is the cheapest day to depart on your flight to Naples?
Our data shows that Tuesday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $1,034. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Naples for around $1,370.
What is the cheapest time of day to depart on your flight to Naples?
Our data shows that the cheapest Chicago to Naples flights are usually those with departure times in the morning. Our users have found flights to Naples in the morning for as low as $705. At noon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,228 per ticket.
What is the cheapest Chicago to Naples flight route?
Fly from Chicago O'Hare Intl to Naples for the best Chicago - Naples flight prices
How far in advance should I book a flight to Naples?
You are more likely to see cheaper flights to Naples from Chicago when booking 8 weeks ahead of your departure date. In general, you can expect to find flights to Naples for around $891 when searching 8 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Naples from Chicago for as low as $757 on momondo.
What cabin class options are available on Chicago to Naples flights?
There are 3 cabin classes available to choose from on Chicago to Naples flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Naples?
Scandinavian Airlines, Turkish Airlines, and American Airlines are the most popular carriers operating from Chicago to Naples
What airlines fly to Naples?
American Airlines, Turkish Airlines and United Airlines are the top three most popular airlines that fly to Naples from Chicago according to our data. American Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Naples. Keep in mind that there are 9 different airlines that fly to Naples on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Naples on average per day?
1 flights are operational daily from Chicago to Naples as of June 2025. The most popular departure time for this route is 8:00PM, with 100% of flights per day taking off in the evening.
How many flights depart from Chicago to Naples on average per week?
As of June 2025, there are 7 flights per week flying from Chicago to Naples. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Chicago to Naples
Cheap Chicago to Naples (CHI to NAP) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Naples
How far is Chicago to Naples by plane?
Naples is 4923.3 mi away from Chicago. A reasonable flight in good conditions will take 9h 20m.
When did momondo last update prices for flights from Chicago to Naples Airport?
Prices for flights from Chicago to Naples Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Naples Airport?
As of June 2025, there are 9 operators available to choose from for flights from Chicago to Naples Airport.
How old do you have to be to fly from Chicago to Naples Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Naples Airport.
What documentation or ID do you need to fly to Naples Airport?
The required travel and health documents for your Naples Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Naples Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Naples?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Naples is Boeing 787-8 Dreamliner (98.06% of total bookings). The next most popular plane models are Boeing 787 Dreamliner (1.29%), Boeing 787-10 Dreamliner (0.32%), and Airbus A330 (0.32%).
What is the most popular airline from Chicago to Naples?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Naples is American Airlines (38% of total bookings). The next most popular airlines are Turkish Airlines (15%), ITA Airways (14%), and United Airlines (9%).
Best airlines flying from Chicago to Naples
Compare and see reviews for airlines that fly from Chicago to Naples with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $497 | Free Cancellation | Rating 6.6 7,008 reviews | |||
| PriceFrom $536 | Free Cancellation | Rating 7.3 3,848 reviews | |||
| PriceFrom $581 | Free Cancellation | Rating 7.8 1,358 reviews | |||
| PriceFrom $594 | Free Cancellation | Rating 6.7 7,136 reviews | |||
| PriceFrom $602 | Free Cancellation | Rating 7.5 1,623 reviews | |||
| PriceFrom $627 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $640 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $679 | Free Cancellation | Rating 6.7 990 reviews | |||
| PriceFrom $686 | Free Cancellation | Rating 7.1 1,117 reviews |
American Airlines Flights From Chicago to Naples
American Airlines is one of the most popular airlines flying from Chicago to Naples, operating 7 flights/week on average for this route. A good American Airlines flight deal for Chicago to Naples starts from $640 round-trip, up to an average price of $1,202. Our users have rated American Airlines at 7.2/10.
Traveling to a place near Naples?
Book flights to Naples if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Naples?
Finding the right flight to Naples from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Naples quick and easy, saving you time and money.
Can I find flights from Chicago to Naples with flexible booking policies on momondo?
Yes. All flights to Naples from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Naples?
momondo helps you find the best flight between Chicago and Naples by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Naples right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Naples flights. All you need is a valid email address and we will do the rest; it is that quick and easy.