Cheap flights from Chicago to Naples

Flight deals from Chicago to Naples

Below you can see the best deals on flights Chicago — Naples for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 13 October, from $359.

Top 10 cheap flights from Chicago to Naples

About the Chicago — Naples flight

Looking for cheap flights from Chicago to Naples? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Naples ticket online at the best price.

The route has direct flights — around 14 flights per week, flights are operated by American Airlines, a nonstop flight takes about 10 h 26 min, the distance between the cities is around 7,949 km.

Planning your trip? You may find our Naples travel guide, how to get from the airport into town and Naples weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

from $359Min. price

OctoberCheapest

DecemberPeak season

YesDirect flights

7,949 kmDistance

10 h 26 minTravel time

1Airlines

14 / wkFlights

Flight schedule from Chicago to Naples

The table shows direct flights from Chicago to Naples on the selected date. The flight takes approximately 10 h 26 min. Regular flights are operated by American Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Naples International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today

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Last update: 21 Sep 2026

Airline

Flight

Departure

Arrival

Duration

Days

Status

Below is a calendar of the lowest flight ticket prices for Chicago — Naples by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $359 in October, and the most expensive are around $599 in December. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

Prices by month

Average one-way fares from Chicago to Naples by month. Tickets are usually cheapest in November (around $435) and priciest in December (about $666) — use the table and chart below to pick the best time to fly.

Month	Average price	Level	Month	Average price	Level	Month	Average price	Level
Jan	$481	low	May	$574	medium	Sep	$592	medium
Feb	$463	low	Jun	$629	high	Oct	$500	low
Mar	$509	medium	Jul	$648	high	Nov	$435	low
Apr	$537	medium	Aug	$638	high	Dec	$666	high

Some values are estimated based on seasonality.

When to fly

Weather in Naples: it is warmest in August (up to 30 °C on average) and coolest in January (around 12 °C). The driest month is July.

Tickets are usually cheapest in October and most expensive in December. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Naples

Dry and wet days · Naples

Wind speed and direction · Naples

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How to get the best deal on a Chicago — Naples ticket

Book ahead: fares for Chicago — Naples are usually lower 3–8 weeks before departure than at the last minute.
Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
Chicago is served by more than one airport — compare fares and travel time to each before you book.
The cheapest month to fly to Naples is usually October — plan your trip around it if your dates are flexible.
Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Flights on the Chicago — Naples route are operated by 1 airline; American Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

American AirlinesAA
5x/week
WebsiteFleet: 965211M pax/year
- Direct flight ORD → NAP5x/week
100.0%Open →

Cities and airports on the Chicago — Naples route

Flights Chicago — Naples depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Naples International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI

United States

About the city How to get there Weather All about the country United States

Arrival

Naples

NAP

Italy

About the city How to get there Weather All about the country Italy

Departure airports

O'Hare International AirportORD
About the airport
Chicago Midway International AirportMDW
About the airport
Midway International AirportNOH
About the airport
Chicago Rockford International AirportRFD
About the airport

Arrival airports

Naples International AirportNAP
About the airport

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Frequently asked questions about the Chicago — Naples flight

How long is the flight from Chicago to Naples?

A nonstop Chicago — Naples flight takes about 10 h 26 min — the distance between the cities is around 7,949 km.

How far is it from Chicago to Naples?

The distance from Chicago to Naples is about 7,949 km, which a nonstop flight covers in around 10 h 26 min.

Are there direct flights from Chicago to Naples?

Yes, there are nonstop flights Chicago — Naples — around 14 flights per week.

Which airlines fly from Chicago to Naples?

Airlines operating Chicago — Naples include American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Naples flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Naples International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Naples?

The price of a Chicago — Naples ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in December. Tickets typically cost between $359 and $599. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Naples?

Flights Chicago — Naples are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Naples?

To catch a low fare Chicago — Naples, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Naples

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