Cheap Flights from Chicago, IL to Naples from $278
Return flight: Naples – Chicago
On Cheapflightsplus.com you will find 1000 connecting flights from Chicago to Naples. You can compare airfare deals from 21 airlines and multiple travel sites from $278, book and save on cheap plane tickets and last minute offers. Also check out CHI-NAP flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Chicago to Naples 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: $278 (one-way), $477 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Chicago to Naples Today
Take a look at the list of non stop flights and flights with layovers from Chicago to Naples with the lowest price of $278. Take a look at the list of flights with layovers from Chicago to Naples from $278. There’re no direct flights. The fastest connecting flight – 11h 15m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $401 | 18:15 Chicago O'Hare International | 18:20+1 день Naples Naples | 17h 5m layover 5h 50m - Lisbon | TAP Portugal | TP244 TP884 |
| from $411 | 11:25 Chicago O'Hare International | 08:20+1 день Naples Naples | 13h 55m layover 1h 10m - Istanbul | Turkish Airlines | TK186 TK1453 |
| from $416 | 10:40 Chicago O'Hare International | 09:40+1 день Naples Naples | 16h 0m layover 5h 41m - Montreal | Air Canada | AC522 AC882 |
| from $278 | 19:39 Chicago O'Hare International | 11:00+3 дня Naples Naples | 56h 21m layover 21h 8m - Orlando 20h 55m - London | Spirit Airlines | NK507 Z0784 U26503 |
| from $282 | 20:12 Chicago O'Hare International | 22:40+2 дня Naples Naples | 43h 28m layover 18h 49m - New York 12h 40m - London | Spirit Airlines | NK919 Z0702 U28341 |
| from $286 | 17:10 Chicago O'Hare International | 19:40+1 день Naples Naples | 19h 30m layover 3h 47m - New York 4h 15m - Paris | Spirit Airlines | NK328 N0302 TO3828 |
| from $290 | 19:25 Chicago O'Hare International | 08:20+2 дня Naples Naples | 29h 55m layover 0h 55m - Reykjavik 16h 50m - Berlin | Icelandair | FI852 FI528 U25051 |
| from $300 | 22:15 Chicago O'Hare International | 20:50+2 дня Naples Naples | 39h 35m layover 22h 40m - Reykjavik 5h 10m - Manchester | Icelandair | FI856 FI440 U22125 |
| from $304 | 12:52 Chicago O'Hare International | 20:40+1 день Naples Naples | 24h 48m layover 6h 24m - Toronto 6h 15m - Dublin | Air Canada | AC4899 WS34 FR6840 |
| from $304 | 08:55 Chicago O'Hare International | 20:40+1 день Naples Naples | 28h 45m layover 10h 21m - Toronto 6h 15m - Dublin | Air Canada | AC5212 WS34 FR6840 |
| from $304 | 07:10 Chicago O'Hare International | 20:40+1 день Naples Naples | 30h 30m layover 12h 12m - Toronto 6h 15m - Dublin | Air Canada | AC4986 WS34 FR6840 |
| from $308 | 20:12 Chicago O'Hare International | 09:20+3 дня Naples Naples | 54h 8m layover 24h 9m - New York 17h 45m - Barcelona | Spirit Airlines | NK919 VY9798 VY6500 |
| from $325 | 13:03 Chicago O'Hare International | 22:45+1 день Naples Naples | 26h 42m layover 3h 39m - Orlando 9h 5m - London | Spirit Airlines | NK1108 Z0784 U28341 |
| from $328 | 17:10 Chicago O'Hare International | 22:05+1 день Naples Naples | 21h 55m layover 3h 47m - New York 6h 40m - Paris | Spirit Airlines | NK328 N0302 AF1578 |
| from $328 | 12:00 Chicago O'Hare International | 20:40+1 день Naples Naples | 25h 40m layover 7h 32m - Toronto 6h 15m - Dublin | Air Canada | AC8904 WS34 FR6840 |
| from $328 | 10:00 Chicago O'Hare International | 20:40+1 день Naples Naples | 27h 40m layover 9h 32m - Toronto 6h 15m - Dublin | Air Canada | AC8902 WS34 FR6840 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on August 02, 2025
Flight Schedule Chicago (Illinois) to Naples
Full flight schedule will help you in detecting at what time planes fly from Chicago to Naples. 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 |
|---|---|---|---|---|
|
06:00 — 07:00
+1 day
|
06:00 — 09:13
UA1658
United Airlines
Chicago — Newark
6h 55m stop
16:15 — 07:00
UA964
United Airlines
Newark — Naples
|
18h including layover |
Find flight
from$575 |
|
|
07:11 — 09:40
+1 day
|
07:11 — 10:40
AC3079
Air Canada
Chicago — Montreal
8h 55m stop
19:35 — 09:40
AC882
Air Canada
Montreal — Naples
|
19h 29m including layover |
Find flight
from$478 |
|
|
07:15 — 11:40
+1 day
|
07:10 — 10:28
UA563
United Airlines
Chicago — Newark
10h 12m stop
20:45 — 11:40
UA966
United Airlines
Newark — Naples
|
21h 25m including layover |
Find flight
from$517 |
|
|
08:40 — 09:40
+1 day
|
08:40 — 11:56
AC8958
Air Canada
Chicago — Montreal
7h 38m stop
19:35 — 09:40
AC882
Air Canada
Montreal — Naples
|
18h including layover |
Find flight
from$478 |
|
|
08:47 — 11:40
+1 day
|
08:45 — 12:09
UA2691
United Airlines
Chicago — Newark
8h 34m stop
20:45 — 11:40
UA966
United Airlines
Newark — Naples
|
19h 53m including layover |
Find flight
from$517 |
|
|
10:40 — 09:40
+1 day
|
10:40 — 13:54
AC522
Air Canada
Chicago — Montreal
5h 41m stop
19:35 — 09:40
AC882
Air Canada
Montreal — Naples
|
16h including layover |
Find flight
from$416 |
|
|
10:40 — 09:40
+1 day
|
10:40 — 13:56
AC8960
Air Canada
Chicago — Montreal
5h 37m stop
19:35 — 09:40
AC882
Air Canada
Montreal — Naples
|
16h including layover |
Find flight
from$478 |
|
|
11:25 — 08:20
+1 day
|
11:25 — 05:45
TK186
Turkish Airlines
Chicago — Istanbul
1h 10m stop
06:55 — 08:20
TK1453
Turkish Airlines
Istanbul — Naples
|
13h 55m including layover |
Find flight
from$411 |
|
|
11:25 — 15:00
+1 day
|
11:25 — 05:45
TK186
Turkish Airlines
Chicago — Istanbul
7h 45m stop
13:30 — 15:00
TK1463
Turkish Airlines
Istanbul — Naples
|
20h 35m including layover |
Find flight
from$412 |
|
|
14:20 — 14:00
+1 day
|
14:20 — 06:10
LX7
SWISS International Air Lines
Chicago — Zurich
6h 10m stop
12:20 — 14:00
LX1710
SWISS International Air Lines
Zurich — Naples
|
16h 40m including layover |
Find flight
from$444 |
|
|
14:20 — 18:30
+1 day
|
14:20 — 06:10
LX7
SWISS International Air Lines
Chicago — Zurich
10h 40m stop
17:25 — 19:10
LX1714
SWISS International Air Lines
Zurich — Naples
|
21h 10m including layover |
Find flight
from$459 |
|
|
15:35 — 12:20
+1 day
|
15:35 — 07:05
LH437
Lufthansa
Chicago — Munich
3h 30m stop
10:35 — 12:20
LH1876
Lufthansa
Munich — Naples
|
13h 45m including layover |
Find flight
from$435 |
|
|
15:35 — 16:35
+1 day
|
15:35 — 07:05
LH437
Lufthansa
Chicago — Munich
7h 45m stop
14:50 — 16:35
LH1878
Lufthansa
Munich — Naples
|
18h including layover |
Find flight
from$486 |
|
|
16:00 — 17:55
+1 day
|
16:00 — 07:20
LH431
Lufthansa
Chicago — Frankfurt
8h 35m stop
15:55 — 17:55
LH336
Lufthansa
Frankfurt — Naples
|
18h 55m including layover |
Find flight
from$490 |
|
|
16:55 — 12:00
+1 day
|
16:55 — 06:50
BA294
British Airways
Chicago — London
1h 15m stop
06:30 — 10:20
BA534
British Airways
London — Naples
|
12h 5m including layover |
Find flight
from$466 |
|
|
17:10 — 15:25
+1 day
|
17:10 — 08:10
AF137
Air France
Chicago — Paris
5h stop
17:20 — 19:35
TO3828
Transavia France
Paris — Naples
|
15h 15m including layover |
Find flight
from$505 |
|
|
17:10 — 19:00
+1 day
|
17:10 — 08:10
AF137
Air France
Chicago — Paris
8h 30m stop
16:40 — 19:00
U24839
EasyJet
Paris — Naples
|
18h 50m including layover |
Find flight
from$517 |
|
|
18:10 — 11:40
+2 days
|
18:00 — 08:00
TP244
TAP Portugal
Chicago — Lisbon
23h 25m stop
07:30 — 11:40
TP882
TAP Portugal
Lisbon — Naples
|
34h 30m including layover |
Find flight
from$476 |
|
|
18:15 — 18:20
+1 day
|
18:00 — 07:55
TP244
TAP Portugal
Chicago — Lisbon
5h 50m stop
14:10 — 18:20
TP884
TAP Portugal
Lisbon — Naples
|
17h 5m including layover |
Find flight
from$401 |
|
|
19:50 — 19:40
+1 day
|
19:50 — 14:40
TK6
Turkish Airlines
Chicago — Istanbul
3h 35m stop
18:15 — 19:40
TK1879
Turkish Airlines
Istanbul — Naples
|
16h 50m including layover |
Find flight
from$411 |
|
|
19:50 — 08:20
+2 days
|
19:50 — 14:40
TK6
Turkish Airlines
Chicago — Istanbul
16h 15m stop
06:55 — 08:20
TK1453
Turkish Airlines
Istanbul — Naples
|
29h 30m including layover |
Find flight
from$413 |
|
|
20:50 — 11:40
+2 days
|
20:50 — 10:50
TP242
TAP Portugal
Chicago — Lisbon
20h 40m stop
07:30 — 11:40
TP882
TAP Portugal
Lisbon — Naples
|
31h 50m including layover |
Find flight
from$564 |
|
|
21:24 — 07:00
+2 days
|
21:24 — 00:45
UA396
United Airlines
Chicago — Newark
15h 30m stop
16:15 — 07:00
UA964
United Airlines
Newark — Naples
|
26h 36m including layover |
Find flight
from$474 |
|
|
21:24 — 11:40
+2 days
|
21:24 — 00:45
UA396
United Airlines
Chicago — Newark
20h stop
20:45 — 11:40
UA966
United Airlines
Newark — Naples
|
31h 16m including layover |
Find flight
from$474 |
|
|
22:30 — 17:55
+1 day
|
22:30 — 14:05
LH433
Lufthansa
Chicago — Frankfurt
1h 50m stop
15:55 — 17:55
LH336
Lufthansa
Frankfurt — Naples
|
12h 25m including layover |
Find flight
from$490 |
|
|
22:30 — 12:15
+2 days
|
22:30 — 14:05
LH433
Lufthansa
Chicago — Frankfurt
20h 10m stop
10:15 — 12:15
LH334
Lufthansa
Frankfurt — Naples
|
30h 45m including layover |
Find flight
from$516 |
|
|
23:45 — 15:00
+2 days
|
23:45 — 18:05
TK156
Turkish Airlines
Chicago — Istanbul
19h 25m stop
13:30 — 15:00
TK1463
Turkish Airlines
Istanbul — Naples
|
32h 15m including layover |
Find flight
from$412 |
|
|
23:45 — 08:20
+2 days
|
23:45 — 18:05
TK156
Turkish Airlines
Chicago — Istanbul
12h 50m stop
06:55 — 08:20
TK1453
Turkish Airlines
Istanbul — Naples
|
25h 35m including layover |
Find flight
from$415 |
|
*Departure and arrival times - local. Updated on August 2, 2025
Flight Information
Below we will explain in detail what the flights cost on the destination from Chicago to Naples depends on and how to choose the most interesting flight option for you.
Distance between Chicago and Naples is 7928 miles. Time difference between the cities is 7h. Airplanes depart 05:01 to 23:45 from 7 Chicago airports and arrive 05:01 to 23:45 to 4 Naples airports. Average flight time is 22h 20m.
- The fastest flight 11h 15m
- Average flight time 22h 20m
- The earliest flight 05:01
- The latest flight 23:45
- Distance 4927 ml
The cheapest months to travel to Naples are september (from 278 $), october (from 282 $), july (from 300 $).
The most expensive months are november (from 620 $), may (from 507 $), december (from 501 $).
What is the lowest airfare Chicago to Naples?
The cheapest plane ticket found by our users is $278. This airfare is for economy class on one-way NK507 flight by Spirit Airlines for September 27, 2025 which leaves O'Hare International in Chicago at 19:39 am and arrives at Naples Naples at 11:00.
Economy class
$278
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Naples is served by 21 regular airline and 4 low-cost airlines. Most of the flights on this route are operated by KLM - 24 departures per week at the price of from $ 516 . And the most expensive tickets are offered by Air Canada airline - from $ 1079.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 1000 flights with layovers on the route. The fastest connecting flight is LX7 by SWISS International Air Lines takes 11h 15m and the cheapest is NK507 by Spirit Airlines for $278.
- KL - KLMfrom $516Find
- AC - Air Canadafrom $304Find
- FI - Icelandairfrom $290Find
- LO - LOTfrom $654Find
- OS - Austrian Airlinesfrom $495Find
- EI - Aer Lingusfrom $628Find
- AF - Air Francefrom $505Find
- JU - Air Serbiafrom $446Find
- LX - SWISS International Air Linesfrom $443Find
- UA - United Airlinesfrom $474Find
- F9 - Frontier Airlinesfrom $376Find
- PD - Porter Airlinesfrom $384Find
See more connecting flights
Airports
You can fly from Chicago to Naples from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).
Chicago airports
- O'Hare International-ORDfrom $278Find
- Midway-MDWfrom $379Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Naples airports
- Beverello Harbor-ZMFFind
- Naples-NAPFind
- Mergellina Harbour-ZMJFind
- Sorrento-RROFind
Airplanes
There are flights to Naples from Chicago by 21 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A350-900from $486Find
Top Domestic Destinations from Chicago
You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.
- from $508Find
- from $74Find
- from $76Find
- from $62Find
- from $66Find
- from $70Find
- from $66Find
- from $61Find
- from $65Find
- from $61Find
Top International Destinations from Chicago
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 $60Find
- from $72Find
- from $73Find
- from $61Find
- from $79Find
- from $73Find
- from $76Find
- from $60Find
- from $59Find
- from $74Find
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.