Cheap Flights from Naples to Chicago, IL from $249
Return flight: Chicago – Naples
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 $249, 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: $249 (one-way), $427 (round-trip).
Direct flights
Check prices for return flight
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 $249. Take a look at the list of flights with layovers from Naples to Chicago from $249. There’re no direct flights. The fastest connecting flight – 12h 5m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $305 | 12:00 Naples Naples | 20:08 Chicago O'Hare International | 15h 8m layover 2h 30m - Philadelphia | British Airways | BA1639 BA5418 |
| from $309 | 07:50 Naples Naples | 15:55 Chicago O'Hare International | 15h 5m layover 3h 20m - London | British Airways | BA427 BA299 |
| from $309 | 07:50 Naples Naples | 18:15 Chicago O'Hare International | 17h 25m layover 5h 40m - London | British Airways | BA427 BA297 |
| from $310 | 20:05 Naples Naples | 13:50+1 день Chicago O'Hare International | 24h 45m layover 13h 15m - London | British Airways | BA425 BA295 |
| from $310 | 20:05 Naples Naples | 15:55+1 день Chicago O'Hare International | 26h 50m layover 15h 20m - London | British Airways | BA425 BA299 |
| from $310 | 20:05 Naples Naples | 18:15+1 день Chicago O'Hare International | 29h 10m layover 17h 40m - London | British Airways | BA425 BA297 |
| from $310 | 07:50 Naples Naples | 11:50+1 день Chicago O'Hare International | 35h 0m layover 23h 25m - London | British Airways | BA427 BA1542 |
| from $316 | 10:40 Naples Naples | 17:50 Chicago O'Hare International | 14h 10m layover 1h 25m - Helsinki | Finnair | AY1792 AY9 |
| from $332 | 11:40 Naples Naples | 19:00 Chicago O'Hare International | 14h 20m layover 2h 30m - Dublin | Aer Lingus | EI451 EI125 |
| from $249 | 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 $298 | 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 |
| from $312 | 10:05 Naples Naples | 19:17+1 день Chicago O'Hare International | 40h 12m layover 6h 20m - Barcelona 19h 55m - New York | Vueling | VY6501 IB2627 NK918 |
| from $316 | 07:50 Naples Naples | 19:27 Chicago O'Hare International | 18h 37m layover 1h 20m - London 3h 54m - Newark | British Airways | BA427 BA185 BA4862 |
| from $316 | 07:50 Naples Naples | 21:21 Chicago O'Hare International | 20h 31m layover 1h 20m - London 5h 38m - Newark | British Airways | BA427 BA185 BA4383 |
| from $317 | 19:40 Naples Naples | 23:31+1 день Chicago O'Hare International | 34h 51m layover 10h 35m - Rome 6h 29m - Los Angeles | Alitalia | AZ1274 N0411 NK3010 |
| from $322 | 11:20 Naples Naples | 23:31+1 день Chicago O'Hare International | 43h 11m layover 19h 0m - Rome 6h 29m - Los Angeles | Alitalia | AZ1264 N0411 NK3010 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 27, 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 | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
06:50 — 14:15
|
06:50 — 09:35
IB1836
Iberia
Naples — Madrid
2h stop
11:35 — 14:15
IB341
Iberia
Madrid — Chicago
|
14h 25m including layover |
Find flight
from$417 |
|
|
06:50 — 14:15
|
06:20 — 09:05
I21836
Iberia Express
Naples — Madrid
2h stop
11:35 — 14:30
AY5659
Finnair
Madrid — Chicago
|
14h 25m including layover |
Find flight
from$439 |
|
|
07:50 — 15:55
|
07:50 — 09:50
BA427
British Airways
Naples — London
3h 20m stop
13:10 — 15:55
BA299
British Airways
London — Chicago
|
15h 5m including layover |
Find flight
from$309 |
|
|
07:50 — 18:15
|
07:50 — 09:50
BA427
British Airways
Naples — London
5h 40m stop
15:30 — 18:15
BA297
British Airways
London — Chicago
|
17h 25m including layover |
Find flight
from$309 |
|
|
08:45 — 16:10
|
07:00 — 09:15
FR1316
Ryanair
Naples — Lisbon
1h 40m stop
13:25 — 16:40
TP243
TAP Portugal
Lisbon — Chicago
|
14h 25m including layover |
Find flight
from$735 |
|
|
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$410 |
|
|
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$411 |
|
|
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$316 |
|
|
10:40 — 17:50
|
10:40 — 15:00
AY1792
Finnair
Naples — Helsinki
1h 25m stop
16:25 — 17:50
IB6422
Iberia
Helsinki — Chicago
|
14h 10m including layover |
Find flight
from$419 |
|
|
11:25 — 13:10
+1 day
|
11:20 — 12:15
AZ1264
Alitalia
Naples — Rome
21h 5m stop
09:25 — 13:10
AZ628
Alitalia
Rome — Chicago
|
32h 45m including layover |
Find flight
from$561 |
|
|
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$332 |
|
|
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$305 |
|
|
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$305 |
|
|
14:45 — 14:15
+1 day
|
14:45 — 17:35
IB1832
Iberia
Naples — Madrid
18h stop
11:35 — 14:15
IB341
Iberia
Madrid — Chicago
|
30h 30m including layover |
Find flight
from$765 |
|
|
14:50 — 14:15
+1 day
|
14:45 — 17:35
IB1832
Iberia
Naples — Madrid
18h stop
11:35 — 14:15
AY5659
Finnair
Madrid — Chicago
|
30h 25m including layover |
Find flight
from$694 |
|
|
15:10 — 13:10
+1 day
|
15:10 — 16:05
AZ1270
Alitalia
Naples — Rome
17h 20m stop
09:25 — 13:10
AZ628
Alitalia
Rome — Chicago
|
29h including layover |
Find flight
from$561 |
|
|
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$410 |
|
|
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$411 |
|
|
18:05 — 15:55
+1 day
|
14:35 — 16:30
BA537
British Airways
Naples — London
17h 20m stop
13:10 — 15:55
BA299
British Airways
London — Chicago
|
28h 50m including layover |
Find flight
from$419 |
|
|
18:05 — 18:15
+1 day
|
18:05 — 19:50
BA537
British Airways
Naples — London
19h 40m stop
15:30 — 18:15
BA297
British Airways
London — Chicago
|
31h 10m including layover |
Find flight
from$519 |
|
|
19:15 — 16:10
+1 day
|
19:10 — 21:30
TP885
TAP Portugal
Naples — Lisbon
15h 10m stop
13:25 — 16:40
TP243
TAP Portugal
Lisbon — Chicago
|
27h 55m including layover |
Find flight
from$462 |
|
|
19:35 — 17:25
+1 day
|
19:35 — 23:55
AY1794
Finnair
Naples — Helsinki
16h 5m stop
16:00 — 17:25
AY9
Finnair
Helsinki — Chicago
|
28h 50m including layover |
Find flight
from$631 |
|
|
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$310 |
|
|
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$310 |
|
|
21:20 — 18:15
+1 day
|
21:20 — 23:10
U28356
EasyJet
Naples — London
16h 20m stop
15:30 — 18:15
BA297
British Airways
London — Chicago
|
27h 55m including layover |
Find flight
from$666 |
|
*Departure and arrival times - local. Updated on June 27, 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 332 $), august (from 407 $), june (from 415 $).
The most expensive months are january (from 660 $), december (from 657 $), november (from 657 $).
What is the lowest airfare Naples to Chicago?
The cheapest plane ticket found by our users is $249. 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
$249
Business class
?
First class
?
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 $ 312 . And the most expensive tickets are offered by SAS airline - from $ 4465.
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 $249.
- VY - Vuelingfrom $312Find
- FI - Icelandairfrom $620Find
- LS - Jet2.comfrom $1119Find
- I2 - Iberia Expressfrom $439Find
- JU - Air Serbiafrom $576Find
- FR - Ryanairfrom $249Find
- LX - SWISS International Air Linesfrom $483Find
- UA - United Airlinesfrom $1207Find
- HV - Transavia Airlinesfrom $622Find
- A3 - Aegean Airlinesfrom $378Find
- FZ - Flydubaifrom $1355Find
- DY - Norwegianfrom $492Find
See more connecting flights
Airports
You can fly from Naples to Chicago from 4 airports (Beverello Harbor, Naples, Mergellina Harbour, Sorrento).
Naples airports
- Beverello Harbor-ZMFFind
- Naples-NAPfrom $249Find
- Mergellina Harbour-ZMJFind
- Sorrento-RROFind
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
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 $411Find
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.
- from $58Find
- from $77Find
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.
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