$317+ Cheap flights from Chicago (CHI) to Naples (NAP)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Jul 13 — Jul 201
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Naples with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Naples are usually found in February or March, booked 52 days in advance, depart on a Sunday or Monday and return on a Saturday
Cheap flight deals from Chicago to Naples
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to NaplesExplore the most affordable flight options available from Chicago to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 13, 2026.
Explore the most affordable flight options available from Chicago to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 13, 2026.
This Mytrip deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:25 pm
ORD
- NAP
2 stops20h 15m
Multiple Airlines
Sat 9/121:25 pm
NAP
- ORD
2 stops33h 35m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$897
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:25 pm
ORD
- NAP
2 stops18h 40m
Multiple Airlines
Mon 9/710:50 am
NAP
- ORD
2 stops17h 35m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$899
This Lufthansa deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:30 pm
ORD
- NAP
1 stop12h 35m
Lufthansa
Thu 7/239:00 am
NAP
- ORD
1 stop16h 15m
Lufthansa
Deal found 6/10![Lufthansa logo]()
$900
This Turkish Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:15 pm
ORD
- NAP
1 stop29h 05m
Turkish Airlines
Sat 11/79:20 am
NAP
- ORD
1 stop17h 00m
Turkish Airlines
Deal found 6/8![Turkish Airlines logo]()
$901
This oojo deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:15 pm
ORD
- NAP
1 stop32h 50m
Scandinavian Airlines
Fri 9/1111:55 am
NAP
- ORD
1 stop35h 15m
Scandinavian Airlines
Deal found 6/10![Scandinavian Airlines logo]()
$902
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:15 pm
ORD
- NAP
1 stop15h 20m
Turkish Airlines
Sat 11/79:20 am
NAP
- ORD
1 stop17h 00m
Turkish Airlines
Deal found 6/10![Turkish Airlines logo]()
$903
This Mytrip deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:25 pm
ORD
- NAP
2 stops18h 40m
Multiple Airlines
Sat 9/198:40 pm
NAP
- ORD
2 stops31h 40m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$904
This Mytrip deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:15 pm
ORD
- NAP
2 stops20h 30m
Multiple Airlines
Sat 10/1711:45 am
NAP
- ORD
3 stops35h 25m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$906
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:45 am
ORD
- NAP
3 stops30h 45m
Multiple Airlines
Mon 9/149:55 pm
NAP
- ORD
3 stops28h 53m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$908
This Gotogate deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:20 pm
ORD
- NAP
1 stop11h 20m
SWISS
Tue 7/217:30 pm
NAP
- ORD
1 stop24h 05m
SWISS
Deal found 6/10![SWISS logo]()
$909
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:23 am
ORD
- NAP
1 stop12h 42m
Delta
Thu 9/310:15 am
NAP
- ORD
1 stop18h 37m
Delta
Deal found 6/11![Delta logo]()
$910
This Gotogate deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:35 pm
ORD
- NAP
1 stop13h 45m
Lufthansa
Fri 7/316:00 am
NAP
- ORD
1 stop20h 55m
Lufthansa
Deal found 6/8![Lufthansa logo]()
$913
Best flights from Chicago to NaplesDiscover carefully curated flight deals from Chicago to Naples that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 13, 2026.
Discover carefully curated flight deals from Chicago to Naples that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 13, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:15 pm
ORD
- NAP
2 stops16h 00m
Scandinavian Airlines
Thu 10/157:35 pm
NAP
- ORD
1 stop27h 35m
Scandinavian Airlines
Deal found 6/12![Scandinavian Airlines logo]()
$904
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:23 am
ORD
- NAP
1 stop12h 42m
Delta
Thu 9/310:15 am
NAP
- ORD
1 stop18h 37m
Delta
Deal found 6/11![Delta logo]()
$910
This Turkish Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:10 pm
ORD
- NAP
1 stop29h 20m
Turkish Airlines
Sun 9/203:45 pm
NAP
- ORD
1 stop24h 55m
Turkish Airlines
Deal found 6/11![Turkish Airlines logo]()
$979
This British Airways deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:30 pm
ORD
- NAP
Nonstop9h 30m
Multiple Airlines
Sat 8/227:40 pm
NAP
- ORD
1 stop27h 15m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$984
This ITA Airways deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:00 pm
ORD
- NAP
1 stop16h 15m
ITA Airways
Thu 8/66:35 am
NAP
- ORD
1 stop13h 35m
ITA Airways
Deal found 6/11![ITA Airways logo]()
$999
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 pm
ORD
- NAP
1 stop34h 40m
TAP AIR PORTUGAL
Fri 10/163:05 pm
NAP
- ORD
2 stops32h 00m
TAP AIR PORTUGAL
Deal found 6/11![TAP AIR PORTUGAL logo]()
$1,001
This KLM deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:35 pm
ORD
- NAP
2 stops15h 35m
KLM
Sat 11/711:50 am
NAP
- ORD
1 stop33h 35m
KLM
Deal found 6/12![KLM logo]()
$1,025
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/131:49 pm
MDW
- NAP
2 stops14h 41m
Delta
Tue 7/216:05 am
NAP
- MDW
2 stops19h 13m
Delta
Deal found 6/9![Delta logo]()
$1,058
This British Airways deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:30 pm
ORD
- NAP
Nonstop9h 30m
Multiple Airlines
Mon 8/108:25 pm
NAP
- ORD
1 stop26h 30m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$1,097
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:42 am
ORD
- NAP
2 stops42h 58m
TAP AIR PORTUGAL
Wed 8/1912:30 pm
NAP
- ORD
1 stop31h 10m
TAP AIR PORTUGAL
Deal found 6/9![TAP AIR PORTUGAL logo]()
$1,169
This ITA Airways deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:00 pm
ORD
- NAP
1 stop16h 20m
ITA Airways
Thu 7/96:35 am
NAP
- ORD
1 stop13h 35m
ITA Airways
Deal found 6/9![ITA Airways logo]()
$1,173
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:48 am
MDW
- NAP
1 stop13h 17m
Delta
Thu 10/156:05 am
NAP
- MDW
2 stops23h 05m
Delta
Deal found 6/8![Delta logo]()
$1,074
This KLM deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:11 pm
MDW
- NAP
1 stop30h 54m
Multiple Airlines
Mon 7/139:05 am
NAP
- MDW
1 stop20h 10m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$1,201
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:27 pm
ORD
- NAP
2 stops16h 03m
Delta
Mon 8/1011:40 am
NAP
- ORD
2 stops19h 17m
Delta
Deal found 6/10![Delta logo]()
$1,121
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/221:49 pm
MDW
- NAP
2 stops14h 41m
Delta
Wed 7/299:05 am
NAP
- MDW
1 stop20h 10m
Delta
Deal found 6/8![Delta logo]()
$1,140
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:25 am
MDW
- NAP
2 stops17h 05m
Delta
Tue 9/296:05 am
NAP
- MDW
2 stops17h 06m
Delta
Deal found 6/8![Delta logo]()
$1,141
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:05 am
MDW
- NAP
1 stop18h 00m
Delta
Fri 10/166:05 am
NAP
- MDW
2 stops17h 45m
Delta
Deal found 6/8![Delta logo]()
$1,185
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:25 am
MDW
- NAP
2 stops17h 05m
Delta
Mon 10/56:05 am
NAP
- MDW
2 stops19h 06m
Delta
Deal found 6/9![Delta logo]()
$1,197
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:05 am
MDW
- NAP
1 stop13h 00m
Delta
Tue 7/216:05 am
NAP
- MDW
2 stops17h 10m
Delta
Deal found 6/8![Delta logo]()
$1,204
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:05 am
MDW
- NAP
1 stop18h 00m
Delta
Fri 9/259:05 am
NAP
- MDW
1 stop20h 20m
Delta
Deal found 6/12![Delta logo]()
$1,269
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
MDW
- NAP
1 stop18h 05m
Delta
Tue 8/410:15 am
NAP
- MDW
2 stops19h 21m
Delta
Deal found 6/11![Delta logo]()
$1,317
Last-minute flights from Chicago to NaplesDiscover last-minute flight deals from Chicago to Naples. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Naples. Data last updated June 13, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:25 pm
ORD
- NAP
2 stops18h 45m
Multiple Airlines
Tue 7/144:20 pm
NAP
- ORD
2 stops30h 40m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$918
This Gotogate deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:20 pm
ORD
- NAP
1 stop11h 20m
SWISS
Tue 7/217:30 pm
NAP
- ORD
1 stop24h 05m
SWISS
Deal found 6/10![SWISS logo]()
$909
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:25 pm
ORD
- NAP
2 stops18h 45m
Multiple Airlines
Tue 7/219:45 pm
NAP
- ORD
2 stops25h 15m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$943
This Mytrip deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:25 pm
ORD
- NAP
3 stops30h 55m
Multiple Airlines
Tue 7/2110:50 pm
NAP
- ORD
2 stops24h 10m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$915
This FlightHub deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:40 pm
ORD
- NAP
1 stop16h 20m
Multiple Airlines
Fri 7/246:55 pm
NAP
- ORD
1 stop25h 00m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$932
This FlightHub deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:40 pm
ORD
- NAP
1 stop16h 20m
SWISS
Fri 7/247:30 pm
NAP
- ORD
1 stop24h 05m
SWISS
Deal found 6/10![SWISS logo]()
$953
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
MDW
- NAP
1 stop18h 05m
Delta
Fri 7/249:05 am
NAP
- MDW
1 stop20h 10m
Delta
Deal found 6/10![Delta logo]()
$1,042
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:05 am
MDW
- NAP
1 stop13h 00m
Delta
Tue 7/216:05 am
NAP
- MDW
2 stops19h 20m
Delta
Deal found 6/10![Delta logo]()
$1,054
This Lufthansa deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:30 pm
ORD
- NAP
1 stop12h 35m
Lufthansa
Thu 7/239:00 am
NAP
- ORD
1 stop16h 15m
Lufthansa
Deal found 6/10![Lufthansa logo]()
$900
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 pm
ORD
- NAP
1 stop17h 20m
TAP AIR PORTUGAL
Wed 7/226:35 am
NAP
- ORD
2 stops37h 05m
TAP AIR PORTUGAL
Deal found 6/12![TAP AIR PORTUGAL logo]()
$954
This Mytrip deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/199:50 am
ORD
- NAP
2 stops23h 35m
Multiple Airlines
Tue 7/286:50 pm
NAP
- ORD
3 stops27h 05m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$949
This Gotogate deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/243:35 pm
ORD
- NAP
1 stop13h 45m
Lufthansa
Fri 7/316:00 am
NAP
- ORD
1 stop20h 55m
Lufthansa
Deal found 6/8![Lufthansa logo]()
$913
One-way flights from Chicago to NaplesSearch for one-way flight options from Chicago to Naples. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
Search for one-way flight options from Chicago to Naples. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:25 pm
ORD
- NAP
2 stops19h 10m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/27:25 pm
ORD
- NAP
2 stops34h 45m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:25 pm
ORD
- NAP
2 stops40h 10m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:25 pm
ORD
- NAP
3 stops44h 05m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:25 pm
ORD
- NAP
2 stops34h 45m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:25 pm
ORD
- NAP
2 stops19h 25m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:25 pm
ORD
- NAP
3 stops40h 20m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:25 pm
ORD
- NAP
3 stops40h 00m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:00 am
MDW
- NAP
2 stops19h 10m
Delta
Deal found 6/11![Delta logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:11 pm
MDW
- NAP
3 stops48h 49m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:25 am
MDW
- NAP
3 stops29h 35m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:45 pm
MDW
- NAP
3 stops31h 40m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$486
Find flight deals from Chicago to Naples
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Naples (NAP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $897 (Mytrip) |
One-way from | $317 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $1,235 |
Good round-trip deal | $1,032 or less |
Good one-way deal | $796 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Naples that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 13, 2026.
Use the filters below to find and compare flights from Chicago to Naples that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 10/4
7:15 pm-6:15 pm
2 stops16h 00m
Naples
Thu 10/15
7:35 pm-4:10 pm
1 stop27h 35m
$904
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Thu 8/20
11:23 am-7:05 am
1 stop12h 42m
Naples
Thu 9/3
10:15 am-9:52 pm
1 stop18h 37m
$910
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Mon 9/7
8:10 pm-8:30 am
1 stop29h 20m
Naples
Sun 9/20
3:45 pm-9:40 am
1 stop24h 55m
$979
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/16
5:30 pm-10:00 am
Nonstop9h 30m
Naples
Sat 8/22
7:40 pm-3:55 pm
1 stop27h 15m
$984
Quickest round-trip
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Wed 7/29
3:00 pm-2:15 pm
1 stop16h 15m
Naples
Thu 8/6
6:35 am-1:10 pm
1 stop13h 35m
$999
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Thu 10/1
6:00 pm-11:40 am
1 stop34h 40m
Naples
Fri 10/16
3:05 pm-4:05 pm
2 stops32h 00m
$1,001
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sat 10/31
1:35 pm-11:10 am
2 stops15h 35m
Naples
Sat 11/7
11:50 am-2:25 pm
1 stop33h 35m
$1,025
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Mon 7/13
1:49 pm-11:30 am
2 stops14h 41m
Naples
Tue 7/21
6:05 am-6:18 pm
2 stops19h 13m
$1,058
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Sun 10/4
10:48 am-7:05 am
1 stop13h 17m
Naples
Thu 10/15
6:05 am-10:10 pm
2 stops23h 05m
$1,074
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sat 8/1
5:30 pm-10:00 am
Nonstop9h 30m
Naples
Mon 8/10
8:25 pm-3:55 pm
1 stop26h 30m
$1,097
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Chicago to Naples
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Naples in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Naples flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Naples flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Naples flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Naples flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Naples flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Naples
Have a flexible travel schedule? Discover the best time to fly to Naples from Chicago with our price prediction graph.
CHI-NAP
ORD-NAP
MDW-NAP
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Naples
CHI-NAP
ORD-NAP
MDW-NAP
What is the cheapest month to book a flight from Chicago to Naples?
Currently, May is the cheapest month in which you can book a flight from Chicago to Naples (average of $371). Flying from Chicago to Naples in July is currently the most expensive (average of $810). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to NAP?
Find hourly flight availability from Chicago to Naples. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 13, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Naples as you normally would.
How much does it cost to fly round-trip from Chicago to Naples?
How often are flights from Chicago to Naples delayed?
About 32% of weekly flights between Chicago and Naples have experienced delays in the past year, with the average delay time being 177 minutes.
What is the most punctual flight time for Chicago to Naples flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Naples flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 32% of flights being delayed.
How far ahead should I book a flight from Chicago to Naples?
The price you pay for your flight from Chicago to Naples may vary depending on when you book. For the best chance of a lower fare, look to book 63 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Naples
Get insights into the airlines that provide service to Naples. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Naples. Reviews last updated June 13, 2026.
See what other customers who have flown with SWISS,Turkish Airlines, andAer Lingus from Chicago to Naples have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.4
Entertainment
6.8
Food
7.1
Boarding
7.7
Crew
8.3
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Entertainment
6.8
Food
7.1
Boarding
7.7
Crew
8.3
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Entertainment
6.8
Food
7.1
Boarding
7.7
Crew
8.3
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Entertainment
6.8
Food
7.1
Boarding
7.7
Crew
8.3
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Entertainment
6.8
Food
7.1
Boarding
7.7
Crew
8.3
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Comfort
7.4
Entertainment
6.8
Food
7.1
Boarding
7.7
Crew
8.3
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Related info for your journey
Find useful and relevant information for your journey from Chicago to Naples. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Naples?
Book flights to Naples if you plan to visit one of these locationsPraiano
Ravello
Conca Dei Marini
Maiori
Sant'Agnello
Vico Equense
Browse thousands of different options on Cheapflights for your next trip
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Complete your trip
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Find flights from Chicago to Naples, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Naples
Explore flights to Naples departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 13, 2026.
Chicago and Naples flights
Browse other Chicago and Naples flight options. Last updated on June 13, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Naples
Discover the top 10 airlines that operate flights from Chicago to Naples. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$448 | Average$543 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$496 | Average$646 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$514 | Average$822 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$530 | Average$660 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$543 | Average$1,149 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$575 | Average$812 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$612 | Average$890 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$633 | Average$1,072 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$633 | Average$833 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$651 | Average$872 | FlexibilityNo cancel fee | On-time79% |