Cheap flights from Naples to Chicago

Naples
NAP
Chicago FSS
CHI

Flight deals from Naples to Chicago

Below you can see the best deals on flights Naples — Chicago 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 5 October, from $485.

Top 10 cheap flights from Naples to Chicago

TP
TP
F9
$ 510

Naples — Chicago

12:30—14:45
9 Sep 2026
33 h 15 m
2 stops
VY
TP
TP
$ 511

Naples — Chicago

21:55—12:40
2 Sep 2026
21 h 45 m
2 stops
VY
TP
TP
$ 514

Naples — Chicago

21:45—16:00
8 Sep 2026
25 h 15 m
2 stops
W4
FI
FI
$ 519

Naples — Chicago

17:00—21:25
10 Sep 2026
35 h 25 m
2 stops
VY
TP
TP
$ 520

Naples — Chicago

21:55—16:00
3 Sep 2026
25 h 5 m
2 stops
VY
TP
TP
$ 520

Naples — Chicago

20:15—16:00
3 Sep 2026
26 h 45 m
2 stops
U2
VY
TP
TP
$ 523

Naples — Chicago

17:55—12:40
2 Sep 2026
25 h 45 m
3 stops
VY
TP
TP
$ 525

Naples — Chicago

21:15—16:00
7 Sep 2026
49 h 45 m
2 stops
V7
FI
FI
$ 526

Naples — Chicago

17:45—21:25
10 Sep 2026
34 h 40 m
2 stops
W4
FI
FI
$ 529

Naples — Chicago

17:00—21:25
26 Aug 2026
59 h 25 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Naples — Chicago flight

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

The route has direct flights — around 19 flights per week, flights are operated by American Airlines, Finnair, British Airways, Iberia, a nonstop flight takes about 10 h 45 min, the distance between the cities is around 7,949 km.

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

Facts about this route

from $430Min. price
OctoberCheapest
AugustPeak season
YesDirect flights
7,949 kmDistance
10 h 45 minTravel time
4Airlines
19 / wkFlights

Flight schedule from Naples to Chicago

The table shows direct flights from Naples to Chicago on the selected date. The flight takes approximately 10 h 45 min. Regular flights are operated by American Airlines, Finnair, British Airways and Iberia. Departures from Naples International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway 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
Any time
Last update: 15 Aug 2026

Flight ticket prices by day: Naples — Chicago

Below is a calendar of the lowest flight ticket prices for Naples — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $430 in October, and the most expensive are around $529 in August. 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.

 
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Prices by month

Average one-way fares from Naples to Chicago by month. Tickets are usually cheapest in January (around $456) and priciest in August (about $1,140) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$456lowMay$660mediumSep$528medium
Feb$456lowJun$804highOct$540medium
Mar$468lowJul$924highNov$468low
Apr$576mediumAug$1,140highDec$492medium

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

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

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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

  • Book ahead: fares for Naples — Chicago 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.
  • The cheapest month to fly to Chicago 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.

Airlines

Flights on the Naples — Chicago route are operated by 4 airlines; American Airlines runs the most flights (around 84% of all flights). Compare carriers, flight shares and schedules below.

  • American AirlinesAA
    5x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight NAP → ORD5x/week
      Duration
      10h 46m
      Days
      MTWTFSS
    84.2%Open →
  • FinnairAY
    1x/week
    WebsiteFleet: 7911M pax/year
    • Direct flight NAP → ORD1x/week
    5.3%Open →
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight NAP → ORD1x/week
    5.3%Open →
  • IberiaIB
    1x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight NAP → ORD1x/week
    5.3%Open →

Cities and airports on the Naples — Chicago route

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

Departure

Naples

NAP
Italy
About the cityHow to get thereWeatherAll about the country Italy
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Naples — Chicago flight

How long is the flight from Naples to Chicago?

A nonstop Naples — Chicago flight takes about 10 h 45 min — the distance between the cities is around 7,949 km.

How far is it from Naples to Chicago?

The distance from Naples to Chicago is about 7,949 km, which a nonstop flight covers in around 10 h 45 min.

Are there direct flights from Naples to Chicago?

Yes, there are nonstop flights Naples — Chicago — around 19 flights per week.

Which airlines fly from Naples to Chicago?

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

Which airports do Naples — Chicago flights use?

Flights from Naples depart from Naples International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway 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 Naples to Chicago?

The price of a Naples — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in August. Tickets typically cost between $430 and $529. Check the current lowest fare and low-price calendar on this page.

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

Flights Naples — Chicago 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 Naples to Chicago?

To catch a low fare Naples — Chicago, 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

See all
ParisMilanLondonMunichRomeMadridFrankfurt am MainZurichPalermoBarcelonaOlbiaAthensAmsterdamSharm El SheikhIbizaCataniaNew York CityMykonosBerlinNiceIstanbulViennaTel AvivPalmaBaselManchesterFiraSplitTiranaBudapestGenevaCorfuCopenhagenVallettaLisbonDublinPhiladelphiaBrusselsBucharestZakynthos

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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