Cheap flights from Naples International to Chicago

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Flight deals from Naples International to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Naples International to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Naples International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Naples International to Chicago flights are currently cheapest in January.

Direct flights from Naples International to Chicago

Alternative Naples International to Chicago routes

Looking for the cheapest, fastest or easiest route from Naples International to Chicago? You could fly into the following airports instead.

Naples to Chicago: Flight information

The things to know before you go.
Cheapest flight found$481
Cheapest month to flyJanuary
Average flight time10 hrs, 50 mins
Most popular airlineAmerican Airlines
Average flights per week7

Finding cheap flights from Naples International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Naples International to Chicago is $481. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
10 hours and 50 minutes is the average flight time from Naples International to Chicago.
American Airlines flies direct from Naples International to Chicago.
There are 7 flights per week flying from Naples International to Chicago, as of November 2025.
The cheapest month to fly from Naples International to Chicago is usually January.
If you're flying from Naples International Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the center of Chicago. We've found flights to this airport from $481.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Naples International Airport to Chicago on Monday, January 26, 2026.
Yes – the average flight time is 10 hours and 50 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In November, the average temperature is usually around 5°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Vueling Airlines offers the cheapest flight tickets to Chicago.

Traveling from Naples International Airport (NAP) to Chicago: what you need to know

  • Expect to be in the air for 9 hours 30 minutes. On average, that's the duration of a direct flight from Naples International Airport to Chicago.

  • Naples International Airport is located in Naples. Based in the UTC-5 timezone, Chicago is six hours behind Naples.

  • Naples International Airport (NAP) to O'Hare International Airport (ORD) is the most popular route, with three departures a week to pick from. If you have things to do before heading off, the last flight from NAP to ORD is with American Airlines at 15:00. Opt for the first departure operated by American Airlines at 15:00 if you want to get on your way earlier.

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This will give you enough time to board your NAP to Chicago flight.

  • Delays at security and check-in are likely if you're traveling during high season, so allow a little extra breathing room. A good rule for peak times? Get there up to four hours early for international flights and two hours for domestic departures.

  • Direct Naples International Airport to Chicago tickets are available for booking. O'Hare International Airport (ORD) is where you'll be landing.

  • American Airlines is a popular airline that operates direct flights from Naples International Airport to Chicago.

  • Think about adding a stopover to potentially land a cheaper flight ticket from NAP to Chicago. Simply deselect 'Direct flights only' during your search. Break up your trip (and maybe save some cash) by stopping at one of these connecting airports:

    • London Heathrow Airport (LHR)

    • Amsterdam Airport Schiphol (AMS)

    • Philadelphia International Airport (PHL)

  • Located around 3 kilometers from the center of Naples, NAP can be reached in about 10 minutes by car (depending on traffic). The journey on public transport will take roughly 25 minutes.

  • Searching for a hotel near NAP? If you're catching an early flight from Naples International Airport to Chicago, these stays set you up for a seamless send-off:

  • 78.31% of flights that take off from Naples International Airport make it to their destination on time.

How to find the cheapest flights from Naples International Airport (NAP) to Chicago

  • $279 is the lowest price we've seen for a one-way Naples International Airport to Chicago flight. A round-trip ticket right now is $481. Depending on when you want to go and the availability, these fares may change.

  • Get cheap flights from NAP to Chicago by booking two months ahead. According to our research, that's the sweet spot for finding a bargain.

  • June is the best month for landing an amazing deal on Naples International Airport to Chicago tickets. If you'd like to travel at a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Cut down on the time spent looking for cheap flights from NAP to Chicago by creating a Price Alert. You'll receive an email or notification on the app when a lower fare becomes available.

  • Tailor your trip with filters. Choose your preferred arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Naples International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes around 35 minutes to reach by car. The center is roughly 40 kilometers away.

  • Getting to the center by public transport takes about 55 minutes.

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from Naples International Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Follow your own route with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and chase adventure across Chicago and beyond.

  • To lock in the lowest price, book your vehicle from O'Hare International Airport about four weeks ahead of your flight from NAP to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 19 kilometers from Chicago Midway International Airport (MDW). After your flight from Naples International Airport to Chicago has hit the runway and you've made your way through the terminal, the drive should be around 20 minutes.

  • If you're catching public transport, it'll take about 45 minutes.

  • Hang the 'Do not disturb' sign on your door and relax at a hotel close to MDW. Here are a few options where you can settle in after your NAP to Chicago flight:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car easy and quick. These trusted providers are located in or around the terminal and will have you on the road before long.

  • Avoid last-minute price surges. Booking your ride four weeks ahead of your arrival at MDW will help you save.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometers from central Chicago. It'll take you about 1 hour 25 minutes to get to the city center by ride-share or cab once you've stepped off your flight from Naples International Airport to Chicago.

  • Public transport can take you there in around 4 hours 15 minutes.

  • Enjoy a more leisurely start to your trip by staying at a hotel near RFD after your NAP to Chicago flight. Recharge after a day of travel or simply take a moment to get your footing in a new city at:

  • Whether you want an economy for a solo adventure or an SUV to transport your group, you'll find the ideal Chicago Rockford International Airport rental car for your needs. Explore the range of wheels available from names such as Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Naples International Airport to Chicago is smart. Along with more affordable prices, you might find it easier to get the make and model you prefer at RFD.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during the high season if you want a bustling atmosphere, but remember that prices are generally higher. Alternatively, book flights from Naples International Airport to Chicago in the off-season when prices are cheaper and crowds are smaller.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Naples International Airport to Chicago flight ticket then if that's your definition of good weather.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from NAP to Chicago around that time if you want to travel in cooler conditions.

More about Chicago

  • Once you've booked your flight from Naples International Airport to Chicago, find a hotel that offers both comfort and a great location. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to explore in this city it can be tricky to know where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top attractions which should be on any good Chicago itinerary.

Explore more of United States

  • Chicago has plenty going for it, but there are so many other corners of United States you'll want to see. Around 451 kilometers south-east of Chicago, a trip to Columbus will keep you on the move. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometers south-east of Chicago, Indianapolis is another essential stop in United States. Experience major highlights starting with The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.