Cheap Flights from Chicago, IL to Naples from $262

Return flight: Naples – Chicago
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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 $262, 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: $262 (one-way), $449 (round-trip).
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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 $262. Take a look at the list of flights with layovers from Chicago to Naples from $262. There’re no direct flights. The fastest connecting flight – 11h 15m.
Price Departure Arrival Flight Duration Airline Flight
from $387
Find flight
11:25
Chicago
O'Hare International
 08:20+1 день
Naples
Naples
 13h 55m
layover
1h 10m - Istanbul
 Turkish Airlines
TK186
TK1453
from $392
Find flight
10:40
Chicago
O'Hare International
 09:40+1 день
Naples
Naples
 16h 0m
layover
5h 41m - Montreal
 Air Canada
AC522
AC882
from $262
Find flight
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 $273
Find flight
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
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 17, 2025
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
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$392
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$387
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$388
11:25 — 19:40
+1 day
11:25 — 05:45 TK186 Turkish Airlines
Chicago — Istanbul
12h 30m stop
18:15 — 19:40 TK1879 Turkish Airlines
Istanbul — Naples
25h 15m
including layover
Find flight
from$388
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$417
14:20 — 08:35
+1 day
14:20 — 06:10 LX7 SWISS International Air Lines
Chicago — Zurich
50m stop
07:05 — 08:45 LX1712 SWISS International Air Lines
Zurich — Naples
11h 15m
including layover
Find flight
from$419
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$432
16:00 — 12:15
+1 day
15:55 — 07:25 LH431 Lufthansa
Chicago — Frankfurt
2h 55m stop
11:20 — 13:20 LH334 Lufthansa
Frankfurt — Naples
13h 15m
including layover
Find flight
from$415
19:05 — 08:35
+2 days
19:05 — 10:50 LX9 SWISS International Air Lines
Chicago — Zurich
20h 10m stop
07:05 — 08:45 LX1712 SWISS International Air Lines
Zurich — Naples
30h 30m
including layover
Find flight
from$417
19:15 — 14:40
+1 day
19:15 — 10:45 SK944 SAS
Chicago — Copenhagen
1h 15m stop
17:05 — 19:45 SK2681 SAS
Copenhagen — Naples
12h 25m
including layover
Find flight
from$413
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$387
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$388
19:50 — 15:00
+2 days
19:50 — 14:40 TK6 Turkish Airlines
Chicago — Istanbul
22h 50m stop
13:30 — 15:00 TK1463 Turkish Airlines
Istanbul — Naples
36h 10m
including layover
Find flight
from$418
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$391
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$391
*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 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 262 $), october (from 265 $), july (from 282 $).

The most expensive months are november (from 584 $), may (from 477 $), december (from 472 $).

What is the lowest airfare Chicago to Naples?

The cheapest plane ticket found by our users is $262. 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
$262
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Business class
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First class
?
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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 $ 486 . And the most expensive tickets are offered by Lufthansa airline - from $ 907.

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 $262.

  • KL - KLM
    from $486
    Find
  • AC - Air Canada
    from $286
    Find
  • FI - Icelandair
    from $273
    Find
  • LO - LOT
    from $616
    Find
  • OS - Austrian Airlines
    from $466
    Find
  • EI - Aer Lingus
    from $591
    Find
  • AF - Air France
    from $475
    Find
  • JU - Air Serbia
    from $419
    Find
  • LX - SWISS International Air Lines
    from $417
    Find
  • UA - United Airlines
    from $446
    Find
  • F9 - Frontier Airlines
    from $354
    Find
  • PD - Porter Airlines
    from $361
    Find
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-ORD
    from $262
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  • Midway-MDW
    from $357
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

Naples airports

  • Beverello Harbor-ZMF
    Find
  • Naples-NAP
    Find
  • Mergellina Harbour-ZMJ
    Find
  • Sorrento-RRO
    Find

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 A350-900
    from $501
    Find

Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

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.

How to book a plane ticket yourself?

How to book an air ticket yourself?
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  • 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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