Cheap Flights from Naples to Chicago, IL from $314

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On Cheapflightsplus.com you will find 984 connecting flights from Naples to Chicago. You can compare airfare deals from 36 airlines and multiple travel sites from $314, book and save on cheap plane tickets and last minute offers. Also check out NAP-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Naples to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $314 (one-way), $538 (round-trip).

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Best Flights from Naples to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Naples to Chicago with the lowest price of $314. Take a look at the list of flights with layovers from Naples to Chicago from $314. There’re no direct flights. The fastest connecting flight – 12h 5m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $384 Find flight	12:00 Naples Naples	20:17 Chicago O'Hare International	15h 17m layover 2h 30m - Philadelphia	British Airways	BA1639 BA5702
from $399 Find flight	10:40 Naples Naples	17:50 Chicago O'Hare International	14h 10m layover 1h 25m - Helsinki	Finnair	AY1792 AY9
from $314 Find flight	22:25 Naples Naples	19:29+1 день Chicago O'Hare International	28h 4m layover 10h 40m - Dublin 4h 25m - Toronto	Ryanair	FR6841 WS35 AC511
from $376 Find flight	15:05 Naples Naples	19:17+1 день Chicago O'Hare International	35h 12m layover 3h 0m - Rome 19h 5m - New York	Alitalia	AZ1270 N0401 NK918

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 17, 2025

Flight Schedule Naples to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Naples to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
07:50 — 11:50 +1 day	07:50 — 09:50 BA427 British Airways Naples — London 23h 25m stop 09:15 — 11:55 BA1542 British Airways London — Chicago	35h including layover	Find flight from$391
07:50 — 17:00	07:50 — 09:50 BA427 British Airways Naples — London 4h 35m stop 14:25 — 17:00 BA1546 British Airways London — Chicago	16h 10m including layover	Find flight from$511
09:20 — 17:55	19:35 — 22:55 TK1454 Turkish Airlines Naples — Istanbul 1h 40m stop 14:10 — 17:35 TK5 Turkish Airlines Istanbul — Chicago	15h 35m including layover	Find flight from$518
09:20 — 09:40 +1 day	09:15 — 13:40 TK1454 Turkish Airlines Naples — Istanbul 17h 45m stop 07:35 — 10:10 TK185 Turkish Airlines Istanbul — Chicago	31h 20m including layover	Find flight from$519
10:40 — 17:50	10:35 — 15:00 AY1792 Finnair Naples — Helsinki 1h 25m stop 16:25 — 17:50 AY9 Finnair Helsinki — Chicago	14h 10m including layover	Find flight from$399
11:40 — 19:00	11:40 — 14:10 EI451 Aer Lingus Naples — Dublin 2h 30m stop 16:40 — 19:00 EI125 Aer Lingus Dublin — Chicago	14h 20m including layover	Find flight from$419
12:00 — 20:17	12:00 — 16:05 BA1639 British Airways Naples — Philadelphia 2h 30m stop 18:45 — 20:22 BA5702 British Airways Philadelphia — Chicago	15h 17m including layover	Find flight from$384
12:00 — 20:08	12:00 — 16:05 BA1639 British Airways Naples — Philadelphia 2h 30m stop 18:35 — 20:08 BA5418 British Airways Philadelphia — Chicago	15h 8m including layover	Find flight from$385
12:00 — 14:12 +1 day	12:00 — 16:05 BA1639 British Airways Naples — Philadelphia 20h 32m stop 12:42 — 14:12 BA5419 British Airways Philadelphia — Chicago	33h 12m including layover	Find flight from$385
16:00 — 17:55 +1 day	16:00 — 19:25 TK1464 Turkish Airlines Naples — Istanbul 19h stop 14:25 — 17:55 TK5 Turkish Airlines Istanbul — Chicago	32h 55m including layover	Find flight from$517
16:00 — 09:40 +1 day	16:00 — 19:25 TK1464 Turkish Airlines Naples — Istanbul 11h 5m stop 06:30 — 09:40 TK185 Turkish Airlines Istanbul — Chicago	24h 40m including layover	Find flight from$518
20:05 — 13:50 +1 day	20:00 — 21:45 BA425 British Airways Naples — London 13h 15m stop 11:05 — 13:50 BA295 British Airways London — Chicago	24h 45m including layover	Find flight from$392
20:05 — 15:55 +1 day	20:00 — 21:45 BA425 British Airways Naples — London 15h 20m stop 13:10 — 15:55 BA299 British Airways London — Chicago	26h 50m including layover	Find flight from$392
20:05 — 18:15 +1 day	20:00 — 21:45 BA425 British Airways Naples — London 17h 40m stop 15:30 — 18:15 BA297 British Airways London — Chicago	29h 10m including layover	Find flight from$392
20:40 — 09:40 +1 day	19:20 — 23:40 TK1880 Turkish Airlines Naples — Istanbul 6h 25m stop 07:35 — 10:10 TK185 Turkish Airlines Istanbul — Chicago	20h including layover	Find flight from$519

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on September 17, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Naples to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Naples and Chicago is 7928 miles. Time difference between the cities is 7h. Airplanes depart 06:00 to 22:35 from 4 Naples airports and arrive 06:00 to 22:35 to 7 Chicago airports. Average flight time is 27h 20m.

The fastest flight 12h 5m
Average flight time 27h 20m
The earliest flight 06:00
The latest flight 22:35
Distance 4927 ml

The cheapest months to travel to Chicago are october (from 314 $), august (from 385 $), september (from 392 $).

The most expensive months are january (from 623 $), december (from 621 $), november (from 621 $).

What is the lowest airfare Naples to Chicago?

The cheapest plane ticket found by our users is $314. This airfare is for economy class on one-way FR6841 flight by Ryanair for October 7, 2025 which leaves Naples in Naples at 22:25 am and arrives at Chicago O'Hare International at 19:29.

Economy class

$314

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Business class

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First class

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Popular Airlines on the Route

The flight Naples — Chicago is served by 36 regular airlines and 10 low-cost airlines. Most of the flights on this route are operated by Vueling - 36 departures per week at the price of from $ 394 . And the most expensive tickets are offered by SAS airline - from $ 5627.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 984 flights with layovers on the route. The fastest connecting flight is LH1889 by Lufthansa takes 12h 5m and the cheapest is FR6841 by Ryanair for $314.

VY - Vueling

from $394

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FI - Icelandair

from $782

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LS - Jet2.com

from $1411

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I2 - Iberia Express

from $554

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JU - Air Serbia

from $726

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FR - Ryanair

from $314

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LX - SWISS International Air Lines

from $610

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UA - United Airlines

from $1697

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HV - Transavia Airlines

from $784

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A3 - Aegean Airlines

from $477

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FZ - Flydubai

from $1707

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DY - Norwegian

from $621

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Airports

You can fly from Naples to Chicago from 4 airports (Beverello Harbor, Naples, Mergellina Harbour, Sorrento).

Naples airports

Beverello Harbor-ZMF

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Naples-NAP

from $314
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Mergellina Harbour-ZMJ

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Sorrento-RRO

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Naples by 36 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-800 (winglets)

from $518

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Top International Destinations from Naples

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Naples — Boston

from $58

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Naples — Chicago

from $77

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.