CHI - NAP

$334 Find Cheap Flights from Chicago to Naples - Compare and Save

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Everything you should know

Cheapest round-trip
$643
Typical prices: $821-$1,300
Multiple Airlines
Thu 11/29Sat 12/15
ORD - NAP • 2 stops
Cheapest one-way
$334
Typical prices: $523-$907
SWISS
Sat 4/21
ORD - NAP • 1 stop
Nonstop flights
There are currently no direct flights between Chicago and Naples. You'll need to take a connecting flight to reach the destination.
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Top routes
Cheapest • 18% average savings
Most popular
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Avoid delays
Most punctual • 69% on-time
Best time • Fewest delays
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Insights
When to book
in advance
Our data shows that travelers who book at least 23 weeks in advance save around 28% compared to booking last minute.
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Insights
When to travel
Cheapest • 35% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $665 (round-trip)
Shortest trip • 12h 08m (one-way)
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Flight Deals

Cheap Flights from Chicago to Naples (CHI-NAP)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Naples

Sun, Nov 29 - Tue, Dec 15
Multiple Airlines Logo
8:10 pm - 7:20 pmORD  Chicago O'Hare Intl-NAP Naples
40h 10m2 stops Lisbon Humberto Delgado Milan Malpensa
Multiple Airlines Logo
2:30 pm - 3:30 pmNAP  Naples-ORD Chicago O'Hare Intl
32h 00m1 stop Lisbon Humberto Delgado
$643Multiple Airlines
Sun, Nov 29 - Tue, Dec 15
Multiple Airlines Logo
8:10 pm - 9:45 amORD  Chicago O'Hare Intl-NAP Naples
30h 35m2 stops Lisbon Humberto Delgado Milan Malpensa
Multiple Airlines Logo
2:30 pm - 3:30 pmNAP  Naples-ORD Chicago O'Hare Intl
32h 00m1 stop Lisbon Humberto Delgado
$654Multiple Airlines
Sun, Nov 29 - Tue, Dec 15
Turkish Airlines Logo
8:15 pm - 8:25 amORD  Chicago O'Hare Intl-NAP Naples
29h 10m1 stop Istanbul
Turkish Airlines Logo
7:35 pm - 10:00 amNAP  Naples-ORD Chicago O'Hare Intl
21h 25m1 stop Istanbul
$668Turkish Airlines
Mon, Apr 5 - Wed, Apr 14
Turkish Airlines Logo
11:20 am - 7:50 pmORD  Chicago O'Hare Intl-NAP Naples
25h 30m1 stop Istanbul
Turkish Airlines Logo
3:55 pm - 9:35 amNAP  Naples-ORD Chicago O'Hare Intl
24h 40m1 stop Istanbul
$692Turkish Airlines
Tue, Feb 2 - Wed, Feb 24
Iberia Logo
1:00 pm - 2:20 pmORD  Chicago O'Hare Intl-NAP Naples
18h 20m2 stops Philadelphia Madrid Barajas
Iberia Logo
6:00 am - 2:55 pmNAP  Naples-ORD Chicago O'Hare Intl
15h 55m1 stop Madrid Barajas
$726Iberia
Tue, Apr 20 - Sat, May 1
British Airways Logo
7:25 pm - 6:05 pmORD  Chicago O'Hare Intl-NAP Naples
15h 40m1 stop London Heathrow
British Airways Logo
11:25 am - 10:34 pmNAP  Naples-ORD Chicago O'Hare Intl
18h 09m2 stops London Heathrow New York John F Kennedy Intl
$768British Airways
Sat, Feb 6 - Sat, Feb 13
SWISS Logo
6:50 pm - 6:45 pmORD  Chicago O'Hare Intl-NAP Naples
16h 55m1 stop Zurich
SWISS Logo
9:55 am - 4:15 pmNAP  Naples-ORD Chicago O'Hare Intl
13h 20m1 stop Zurich
$775SWISS
Sat, Apr 24 - Mon, May 3
British Airways Logo
7:14 pm - 7:35 pmORD  Chicago O'Hare Intl-NAP Naples
41h 21m2 stops Cincinnati Cinci./N. Kentucky London Heathrow
British Airways Logo
7:40 am - 4:25 pmNAP  Naples-ORD Chicago O'Hare Intl
15h 45m1 stop London Heathrow
$787British Airways
Sun, Apr 18 - Thu, Apr 29
SWISS Logo
7:05 pm - 2:05 pmORD  Chicago O'Hare Intl-NAP Naples
12h 00m1 stop Zurich
SWISS Logo
1:20 pm - 12:35 pmNAP  Naples-ORD Chicago O'Hare Intl
30h 15m2 stops Frankfurt am Main Zurich
$798SWISS
Tue, Jan 19 - Sat, Jan 30
Iberia Logo
3:17 pm - 2:20 pmORD  Chicago O'Hare Intl-NAP Naples
16h 03m2 stops Boston Logan Intl Madrid Barajas
Iberia Logo
6:00 am - 6:55 pmNAP  Naples-ORD Chicago O'Hare Intl
19h 55m2 stops Madrid Barajas New York John F Kennedy Intl
$880Iberia
Booking Insights

Price, demand and travel trends for Chicago to Naples flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What is the cheapest Chicago to Naples flight route?

Chicago Midway Airport (MDW) to Naples (NAP) is the cheapest Chicago to Naples route, averaging $735 round-trip. Other Chicago to Naples routes average $1,055, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Chicago to Naples. It’s 16% cheaper than the average day, while Wednesday is the most expensive, with prices 12% higher.

What’s the cheapest month to fly from Chicago to Naples?

•March is the cheapest month to fly from Chicago to Naples at $693 round-trip.
•June ($1,301) and July ($1,177) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 87% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago to Naples the cheapest?

Flights from Chicago to Naples are cheapest 23 weeks before departure. Booking in this window typically costs about 28% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Chicago to Naples flights

Low season

December

Cheapest flight

$334
Beat the crowds with an average 85% drop in travelers.
The most popular month to fly with an average 76% increase in travelers.
One-way flight from Chicago O'Hare Intl 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

Your Chicago to Naples flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago to Naples?

    Three cabin classes are available on flights from Chicago to Naples:

    • Economy Class
    • Premium Economy Class
    • Business Class

  • How long is a flight from Chicago to Naples?

    A nonstop flight from Chicago to Naples takes 00m, covering 4,923 miles.

  • Do I need a passport to fly from Chicago to Naples?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago to Naples flight?

    Round-trip flights from Chicago to Naples range from $821 to $1,300, with an average of $1,074 over the past 12 months. Anything below $821 counts as a good deal.

  • How expensive are last-minute Chicago to Naples flights?

    Last-minute fares on this route (booked within two weeks of departure) run 13% above the $1,074 route average. Book 23 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago to Naples?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $665 round-trip via Kastrup Copenhagen (CPH), compared to $1,212 for nonstop.

  • How does on-time performance compare across airlines flying from Chicago to Naples?

    American Airlines is the only airline operating Chicago to Naples flights. 69% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Chicago to Naples?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $85–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airlines offer Wi-Fi on Chicago to Naples flights?

    Three airlines offer in-flight Wi-Fi on Chicago to Naples flights:

    • American Airlines
    • Iberia
    • Finnair

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Chicago to Naples looking right now?

    One-way fares from Chicago to Naples are currently lower than usual. Average one-way flight prices are about $410, which is 41% below the typical average for this route.

  • What car rental options are available at Naples Airport (NAP)?

    Naples Airport (NAP) hosts 5 major car rental companies, with daily rates averaging $32 for economy cars. Top options include:

    • Ace
    • Galdierirent
    • SURPRICE CAR RENTAL
    • Target Italy
    • Felirent

  • Which airports can I use when flying from Chicago to Naples?

    Flights from Chicago to Naples may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Naples (NAP).

  • What time of day has the fewest delays on flights from Chicago to Naples?

    Afternoon flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Chicago to Naples?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Naples route, 31% of flights were delayed in the past 3 months, with delays averaging 2h 38m.

  • Which airports do connecting flights from Chicago to Naples pass through?

    One-stop flights from Chicago to Naples most commonly connect through:

    • Istanbul (IST) - 41% of one-stop connections
    • Zurich (ZRH) - 17% of one-stop connections
    • Dublin (DUB) - 15% of one-stop connections
    • Rome Fiumicino (FCO) - 7% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago to Naples?

    Yes. Flexible dates can save you up to 26% on flights from Chicago to Naples. Sunday is the cheapest departure day at $908 round-trip on average, while Wednesday is the most expensive at $1,212, a difference of $304.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How much time can I save by choosing a different layover airport from Chicago to Naples?

    Flying via Munich Franz Josef Strauss (MUC) gives the shortest average 1-stop total travel time at 12h 08m, compared with 12h 39m via Zurich (ZRH) and 13h 13m via Dublin (DUB).

  • What is the time difference between Chicago and Naples?

    Naples is 7 hours ahead of Chicago (Central European Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Naples?

    Some of the most popular sights in Naples are Piazza Bellini, Piazza Giuseppe Garibaldi and Piazza del Municipio. These are among the most viewed places in Naples on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago to Naples flights?

    Among airlines operating Chicago to Naples flights:

    • American Airlines: offers extra legroom; offers free seat selection
    • Iberia: offers free seat selection
    • Finnair: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago to Naples flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Iberia: a cabin bag and a checked bag in Economy Class
    • Finnair: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • Are there services for those people with reduced mobility at Naples International Airport?

    Naples International Airport is dedicated to giving the best experience to all passengers especially those with reduced mobility. The airport offers traffic lights with sound indications, paths and tactile maps for the visually impaired not forgetting platforms with accessed ramps. Passengers with reduced mobility should contact the airport 48 hours before their flight in case they need assistance and plan of taking advantage of the services to be provided.

  • Can I find nursing rooms at Chicago International Airport?

    Chicago International Airport has nursing rooms which is located in Terminal 3 Rotunda, next to the Yoga room and Urban Garden. The room has seats, sinks, an outlet, and paper towels.

  • Can I find a business center at Naples International Airport?

    Naples International Airport has multiple business centers which offer services. The Premier Executive Center located in North Naples, Florida. It offers conference rooms, money transfers, and currency exchange.

  • Where can I sleep at Chicago O’Hare International Airport?

    Should you need a place to rest before your flight, there is the Hilton Chicago O’Hare International Airport is located inside the airport and is directly across Terminals 1, 2 and 3 connected by underground walkways. The hotel offers delicacies and alcoholic and non-alcoholic drinks.

Your guide to booking Chicago to Naples flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Sunday departure and avoid flying on Wednesday. On this route, Sunday flights average $908, about $304 less than Wednesday fares (25% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 23 weeks before you fly. On this route, that window historically saves about 28% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to Naples trip for March. Fares historically average $693 round-trip in that month - typically $608 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Kastrup Copenhagen Airport (CPH) can be cheaper than flying direct. The cheapest layover option averages $665 round-trip on this route - about $546 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Naples Airport.

    • Millennium Gold Hotel
    • Luxor Hotel
    • Holiday Inn Naples By IHG
  • Naples International Airport (NAP) offers two options that one can take from the airport to reach the city center. The options consist of a taxi and a bus. Though the taxi is more expensive than the bus it’s the fastest option since one can only use less than 15 minutes to arrive at the city center. One can also use the bus since it is the cheapest method and takes only 15 minutes for one to reach their destination.
  • Chicago offers a variety of parking lots that enable passengers to arrive at terminals in a few minutes. The airport has parking lots like Baymont by Wyndham O’Hare parking, La Quinta Inn Suites ORD Airport Parking and ORD Routes Airport Parking. The lots offer both short and long-term parking where the short-term packing facility is located adjacent to the domestic terminals. Long-term parking facilities are located at Economic Lots F and these lots offer free shuttle buses operating 24 hours a day.
  • If one is planning on extending their stay in Naples, renting a car would come in handy since it will be of help as one moves around. You can find a car rental at Surface Car Rental Capodichino Airport, which is 2 miles from the city center. One can rent a car from companies like Hertz, Budget, Dollar, and Thrifty are all set up to offer a wide range of cars.
  • Chicago O’Hare International Airport (ORD) has six animal relief areas where four are outdoor areas while the other two are inside the airport security. These animal relief areas are located at the Multi-Modal Facility and on the lower levels of Terminals 1, 2, and 3. The animal relief areas have chew toys, pet carriers, plastic bags, and dog treats. The area is covered in synthetic grass, small fire hydrants and a pop-up sprinkler system that cleans and gets rid of waste.
  • You can’t get bored during your flight since Turkish Airlines offers a wide range of options when it comes to entertainment. One can choose from a selection of TV shows, movies, games and music that keeps them entertained when onboard.

More options for your flight from Chicago to Naples

Complete your trip to Naples with a hotel stay or car rental