$308+ Cheap flights from Chicago (CHI) to Naples (NAP)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Oct 10 — Oct 171
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 44 days in advance, depart on a Monday or Tuesday and return on a Saturday
Cheap flight deals from Chicago to Naples
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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 September 10, 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 September 10, 2026.
This Booking.com deal was found by Cheapflights users on 9/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 pm -
1 stop17h 20m
Wed 10/1412:30 pm -
1 stop31h 10m
Deal found 9/6![TAP AIR PORTUGAL logo]()
$608
This Travelocity deal was found by Cheapflights users on 9/9. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/93:16 pm -
2 stops16h 04m
Sun 12/1310:25 pm -
2 stops46h 20m
Deal found 9/9![Iberia logo]()
$613
This Gotogate deal was found by Cheapflights users on 9/10. 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.
Tue 12/87:05 am -
2 stops19h 05m
Sun 12/137:35 pm -
1 stop27h 40m
Deal found 9/10![Multiple Airlines logo]()
$628
This Booking.com deal was found by Cheapflights users on 9/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
1 stop11h 55m
Wed 10/2111:40 am -
1 stop14h 35m
Deal found 9/9![Aer Lingus logo]()
$636
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
1 stop11h 55m
Tue 10/2011:40 am -
1 stop14h 35m
Deal found 9/10![Aer Lingus logo]()
$637
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Tue 10/137:05 pm -
1 stop11h 55m
Tue 10/207:30 pm -
1 stop24h 05m
Deal found 9/10![SWISS logo]()
$638
This Iberia deal was found by Cheapflights users on 9/8. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:10 pm -
1 stop16h 20m
Wed 12/236:00 am -
2 stops21h 20m
Deal found 9/8![Multiple Airlines logo]()
$643
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/92:31 pm -
2 stops16h 49m
Sun 12/1312:40 pm -
1 stop13h 35m
Deal found 9/9![American Airlines logo]()
$644
This British Airways deal was found by Cheapflights users on 9/10. 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.
Tue 10/137:05 pm -
1 stop19h 55m
Tue 10/203:00 pm -
Nonstop10h 50m
Deal found 9/10![British Airways logo]()
$646
This Iberia deal was found by Cheapflights users on 9/10. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop9h 35m
Tue 10/203:00 pm -
Nonstop10h 50m
Deal found 9/10![Iberia logo]()
$649
This Delta deal was found by Cheapflights users on 9/8. 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 10/46:05 am -
1 stop18h 00m
Thu 10/156:05 am -
2 stops18h 55m
Deal found 9/8![Delta logo]()
$779
This Delta deal was found by Cheapflights users on 9/8. 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 9/156:05 am -
1 stop18h 00m
Wed 9/306:05 am -
2 stops19h 28m
Deal found 9/8![Delta logo]()
$781
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 September 10, 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 September 10, 2026.
This Turkish Airlines deal was found by Cheapflights users on 9/6. 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.
Sun 10/48:10 pm -
1 stop16h 40m
Wed 10/148:50 pm -
1 stop19h 50m
Deal found 9/6![Turkish Airlines logo]()
$695
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 10/45:10 pm -
2 stops18h 05m
Tue 10/2010:15 am -
1 stop18h 28m
Deal found 9/9![Delta logo]()
$770
This Scandinavian Airlines deal was found by Cheapflights users on 9/6. 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 -
1 stop16h 30m
Wed 10/1410:05 am -
2 stops37h 05m
Deal found 9/6![Scandinavian Airlines logo]()
$858
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:50 am -
2 stops19h 50m
Fri 10/166:00 am -
2 stops34h 00m
Deal found 9/10![United Airlines logo]()
$937
This Air Canada deal was found by Cheapflights users on 9/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:56 pm -
1 stop32h 44m
Tue 10/206:00 am -
2 stops20h 48m
Deal found 9/5![Air Canada logo]()
$995
This Turkish Airlines deal was found by Cheapflights users on 9/6. 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.
Wed 10/2111:25 am -
1 stop14h 05m
Wed 10/287:35 pm -
1 stop21h 25m
Deal found 9/6![Turkish Airlines logo]()
$705
This Turkish Airlines deal was found by Cheapflights users on 9/10. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:10 pm -
1 stop16h 40m
Sun 10/257:35 pm -
1 stop21h 25m
Deal found 9/10![Turkish Airlines logo]()
$755
This Delta deal was found by Cheapflights users on 9/9. 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 9/196:05 am -
2 stops19h 05m
Tue 9/296:05 am -
2 stops19h 14m
Deal found 9/9![Delta logo]()
$846
This Delta deal was found by Cheapflights users on 9/7. 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 12/11:41 pm -
2 stops19h 09m
Sun 12/136:10 am -
2 stops18h 51m
Deal found 9/7![Delta logo]()
$865
This United Airlines deal was found by Cheapflights users on 9/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/143:45 pm -
2 stops35h 50m
Thu 2/186:30 am -
2 stops18h 13m
Deal found 9/7![United Airlines logo]()
$980
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:05 am -
1 stop21h 35m
Sat 10/36:00 am -
2 stops21h 13m
Deal found 9/10![United Airlines logo]()
$997
This Turkish Airlines deal was found by Cheapflights users on 9/6. 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 10/38:10 pm -
1 stop16h 40m
Sat 10/108:50 pm -
1 stop19h 50m
Deal found 9/6![Turkish Airlines logo]()
$963
This Delta deal was found by Cheapflights users on 9/7. 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 10/76:04 am -
2 stops19h 06m
Wed 10/2110:15 am -
2 stops19h 18m
Deal found 9/7![Delta logo]()
$997
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:45 pm -
2 stops30h 55m
Wed 10/282:15 pm -
1 stop12h 50m
Deal found 9/9![United Airlines logo]()
$1,030
This Delta deal was found by Cheapflights users on 9/8. 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 9/196:05 am -
2 stops19h 05m
Mon 10/56:05 am -
2 stops19h 28m
Deal found 9/8![Delta logo]()
$1,011
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 9/211:00 pm -
2 stops15h 30m
Wed 10/76:05 am -
2 stops17h 42m
Deal found 9/10![Delta logo]()
$1,013
This Delta deal was found by Cheapflights users on 9/10. 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.
Sun 10/46:05 am -
1 stop18h 00m
Thu 10/156:05 am -
2 stops18h 55m
Deal found 9/10![Delta logo]()
$1,064
This Delta deal was found by Cheapflights users on 9/6. 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 10/49:59 am -
2 stops18h 31m
Tue 10/206:05 am -
2 stops18h 55m
Deal found 9/6![Delta logo]()
$1,129
This Delta deal was found by Cheapflights users on 9/8. 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 -
1 stop18h 00m
Sun 10/119:05 am -
1 stop20h 28m
Deal found 9/8![Delta logo]()
$1,132
This Delta deal was found by Cheapflights users on 9/7. 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 10/46:05 am -
1 stop18h 00m
Wed 10/146:05 am -
2 stops17h 09m
Deal found 9/7![Delta logo]()
$1,133
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 10/16:05 am -
1 stop18h 00m
Fri 10/169:05 am -
1 stop20h 28m
Deal found 9/9![Delta logo]()
$1,168
This Delta deal was found by Cheapflights users on 9/8. 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 9/166:05 am -
2 stops19h 05m
Sun 9/209:05 am -
1 stop20h 39m
Deal found 9/8![Delta logo]()
$1,188
Last-minute flights from Chicago to NaplesDiscover last-minute flight deals from Chicago to Naples. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Naples. Data last updated September 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/8. 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 9/156:05 am -
1 stop18h 00m
Wed 9/306:05 am -
2 stops19h 28m
Deal found 9/8![Delta logo]()
$781
This Delta deal was found by Cheapflights users on 9/8. 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 9/166:05 am -
2 stops19h 05m
Sun 9/209:05 am -
1 stop20h 39m
Deal found 9/8![Delta logo]()
$1,188
This Delta deal was found by Cheapflights users on 9/9. 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 9/196:05 am -
1 stop18h 00m
Tue 9/296:05 am -
2 stops19h 14m
Deal found 9/9![Delta logo]()
$841
This Delta deal was found by Cheapflights users on 9/8. 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 9/196:05 am -
1 stop18h 00m
Mon 10/56:05 am -
2 stops19h 28m
Deal found 9/8![Delta logo]()
$1,007
This Booking.com deal was found by Cheapflights users on 9/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 pm -
1 stop17h 20m
Wed 10/1412:30 pm -
1 stop31h 10m
Deal found 9/6![TAP AIR PORTUGAL logo]()
$608
This lol.travel deal was found by Cheapflights users on 9/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:10 pm -
1 stop16h 40m
Tue 10/208:50 pm -
1 stop19h 50m
Deal found 9/6![Turkish Airlines logo]()
$662
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
Tue 10/137:05 pm -
1 stop11h 55m
Tue 10/207:30 pm -
1 stop24h 05m
Deal found 9/10![SWISS logo]()
$638
This British Airways deal was found by Cheapflights users on 9/10. 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.
Tue 10/137:05 pm -
1 stop19h 55m
Tue 10/203:00 pm -
Nonstop10h 50m
Deal found 9/10![British Airways logo]()
$646
This Iberia deal was found by Cheapflights users on 9/10. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:25 pm -
Nonstop9h 35m
Tue 10/203:00 pm -
Nonstop10h 50m
Deal found 9/10![Iberia logo]()
$649
This Booking.com deal was found by Cheapflights users on 9/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
1 stop11h 55m
Wed 10/2111:40 am -
1 stop14h 35m
Deal found 9/9![Aer Lingus logo]()
$636
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
1 stop11h 55m
Tue 10/2011:40 am -
1 stop14h 35m
Deal found 9/10![Aer Lingus logo]()
$637
This FlightHub deal was found by Cheapflights users on 9/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:25 pm -
Nonstop9h 35m
Tue 10/203:00 pm -
Nonstop10h 50m
Deal found 9/8![Finnair logo]()
$665
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 September 10, 2026.
Search for one-way flight options from Chicago to Naples. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/57:25 pm -
3 stops38h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/33:20 pm -
3 stops41h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$313
This Mytrip deal was found by Cheapflights users on 9/6. 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 10/211:05 am -
3 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$319
This Expedia deal was found by Cheapflights users on 9/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:10 pm -
1 stop16h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![British Airways logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/312:56 pm -
3 stops49h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$323
This BusinessClass deal was found by Cheapflights users on 9/8. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/81:22 pm -
2 stops15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![British Airways logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/410:25 pm -
3 stops32h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/117:25 pm -
3 stops38h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 3/83:55 pm -
2 stops20h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/211:45 am -
2 stops27h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 9/6. 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 1/76:00 am -
2 stops32h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/112:54 pm -
3 stops50h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$409
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 September 10, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $608 (Booking.com) |
One-way from | $308 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $963 |
Good round-trip deal | $1,082 or less |
Good one-way deal | $614 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 7,457,451 searches. Data last updated September 10, 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
MDW Chicago Midway - NAP Naples
MDWNAP
Chicago Midway
Sat 10/3
3:20 pm-4:00 pm
3 stops41h 40m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$313
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Wed 12/9
9:50 pm-5:45 pm
1 stop12h 55m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$341
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Tue 3/2
9:50 pm-5:45 pm
1 stop12h 55m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$341
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Mon 3/8
9:50 pm-5:45 pm
1 stop12h 55m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$341
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Tue 12/8
9:50 pm-5:45 pm
1 stop12h 55m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$341
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Wed 3/3
9:50 pm-5:45 pm
1 stop12h 55m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$341
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Tue 3/2
11:30 am-9:35 am
2 stops15h 05m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$347
Quickest round-trip
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Mon 12/7
6:05 pm-1:30 pm
1 stop12h 25m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$353
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Sun 3/7
6:00 am-1:30 pm
2 stops24h 30m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$359
ChicagoNaples
ORD Chicago O'Hare Intl - NAP Naples
ORDNAP
Chicago O'Hare Intl
Sat 3/6
9:25 pm-1:30 pm
2 stops33h 05m
Naples
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$370
Showing 1-10 of 39 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 September.
| 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 Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Naples flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Naples flight deals on Cheapflights vs. Ovago >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 Ovago the most. Ovago 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, February is the cheapest month in which you can book a flight from Chicago to Naples (average of $569). Flying from Chicago to Naples in June is currently the most expensive (average of $1,235). 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 September 10, 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.
Weekly flight availability from Chicago to Naples
Explore weekly flight availability from Chicago to Naples. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 10, 2026.
The most flights from CHI to NAP are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Chicago to Naples?
Airfare is below average for this route at the moment.
Chicago to Naples flights typically cost between $786 and $1,111 in October.The cheapest round-trip price found within the last 5 days was $608 on TAP AIR PORTUGAL (Oct 4-Oct 14).
How often are flights from Chicago to Naples delayed?
About 30% of weekly flights between Chicago and Naples have experienced delays in the past year, with the average delay time being 158 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?
Thursday tends to have the lowest number of delays on this route, whereas Wednesday 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 30% 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 2 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 September 10, 2026.
See what other customers who have flown with Turkish Airlines,Aer Lingus, andAmerican Airlines 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.
Boarding
7.3
Comfort
7.3
Crew
7.8
Food
7.5
Overall
7.4
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Crew
7.8
Food
7.5
Overall
7.4
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Crew
7.8
Food
7.5
Overall
7.4
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Crew
7.8
Food
7.5
Overall
7.4
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Crew
7.8
Food
7.5
Overall
7.4
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Crew
7.8
Food
7.5
Overall
7.4
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
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 locationsRavello
Maiori
Praiano
Sant'Agnello
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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 September 10, 2026.
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Browse other Chicago and Naples flight options. Last updated on September 10, 2026.
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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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$493 | Average$796 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$496 | Average$695 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$501 | Average$707 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$514 | Average$837 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$543 | Average$694 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$567 | Average$1,093 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$612 | Average$938 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$626 | Average$899 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$651 | Average$872 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$725 | Average$1,235 | FlexibilityNo cancel fee | On-time71% |