$374+ Cheap flights from Naples (NAP) to Chicago (CHI)
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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
May 28 — Jun 41
Round-trip
1 adult, Economy
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Find cheap flights from Naples to Chicago 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
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Cheapest flights from Naples to ChicagoExplore the most affordable flight options available from Naples to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
Explore the most affordable flight options available from Naples to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
This lol.travel deal was found by Cheapflights users on 4/27. 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.
Wed 9/306:35 am
NAP
- ORD
1 stop13h 35m
ITA Airways
Fri 10/233:00 pm
ORD
- NAP
1 stop12h 35m
ITA Airways
Deal found 4/27![ITA Airways logo]()
$570
This lol.travel deal was found by Cheapflights users on 4/25. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
Finnair
Mon 5/255:30 pm
ORD
- NAP
Nonstop9h 30m
Finnair
Deal found 4/25![Finnair logo]()
$580
This lol.travel deal was found by Cheapflights users on 4/24. 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.
Thu 5/213:00 pm
NAP
- ORD
Nonstop10h 55m
Finnair
Mon 5/255:30 pm
ORD
- NAP
Nonstop9h 30m
Finnair
Deal found 4/24![Finnair logo]()
$586
This lol.travel deal was found by Cheapflights users on 4/27. 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.
Tue 9/86:35 am
NAP
- ORD
1 stop13h 35m
ITA Airways
Wed 9/163:00 pm
ORD
- NAP
1 stop20h 50m
ITA Airways
Deal found 4/27![ITA Airways logo]()
$596
This lol.travel deal was found by Cheapflights users on 4/27. 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.
Tue 9/83:00 pm
NAP
- ORD
Nonstop10h 50m
British Airways
Wed 9/167:05 pm
ORD
- NAP
1 stop19h 55m
British Airways
Deal found 4/27![British Airways logo]()
$612
This lol.travel deal was found by Cheapflights users on 4/24. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
British Airways
Mon 5/257:05 pm
ORD
- NAP
1 stop12h 25m
British Airways
Deal found 4/24![British Airways logo]()
$613
This lol.travel deal was found by Cheapflights users on 4/24. 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.
Thu 5/213:00 pm
NAP
- ORD
Nonstop10h 55m
British Airways
Mon 5/257:05 pm
ORD
- NAP
1 stop12h 25m
British Airways
Deal found 4/24![British Airways logo]()
$620
This Delta deal was found by Cheapflights users on 4/25. 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 6/96:05 am
NAP
- MDW
2 stops19h 26m
Delta
Tue 6/166:05 am
MDW
- NAP
2 stops19h 05m
Delta
Deal found 4/25![Delta logo]()
$716
This Delta deal was found by Cheapflights users on 4/27. 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.
Fri 6/126:05 am
NAP
- MDW
2 stops19h 26m
Delta
Tue 6/166:00 am
MDW
- NAP
2 stops19h 10m
Delta
Deal found 4/27![Delta logo]()
$717
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 5/226:05 am
NAP
- MDW
2 stops19h 28m
Delta
Thu 5/286:23 am
MDW
- NAP
2 stops18h 47m
Delta
Deal found 4/26![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 4/26. 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
NAP
- MDW
2 stops19h 26m
Delta
Fri 10/26:00 am
MDW
- NAP
2 stops19h 10m
Delta
Deal found 4/26![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 4/27. 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 5/236:05 am
NAP
- MDW
2 stops18h 51m
Delta
Fri 5/291:59 pm
MDW
- NAP
2 stops14h 31m
Delta
Deal found 4/27![Delta logo]()
$735
Best flights from Naples to ChicagoDiscover carefully curated flight deals from Naples to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
Discover carefully curated flight deals from Naples to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
American Airlines
Mon 5/255:30 pm
ORD
- NAP
Nonstop9h 30m
American Airlines
Deal found 4/25![American Airlines logo]()
$634
This Finnair deal was found by Cheapflights users on 4/23. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
Finnair
Mon 5/255:30 pm
ORD
- NAP
Nonstop9h 30m
Finnair
Deal found 4/23![Finnair logo]()
$636
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 6/126:05 am
NAP
- MDW
2 stops19h 26m
Delta
Tue 6/166:05 am
MDW
- NAP
2 stops19h 05m
Delta
Deal found 4/23![Delta logo]()
$682
This KLM deal was found by Cheapflights users on 4/26. 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.
Fri 6/126:05 am
NAP
- ORD
1 stop16h 05m
Multiple Airlines
Tue 6/169:48 am
ORD
- NAP
1 stop14h 17m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$712
This KLM deal was found by Cheapflights users on 4/25. 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.
Tue 6/910:15 am
NAP
- ORD
1 stop18h 33m
KLM
Tue 6/166:05 am
ORD
- NAP
1 stop19h 05m
KLM
Deal found 4/25![KLM logo]()
$712
This British Airways deal was found by Cheapflights users on 4/24. 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.
Mon 5/187:40 am
NAP
- ORD
1 stop17h 35m
British Airways
Mon 5/257:05 pm
ORD
- NAP
1 stop19h 55m
British Airways
Deal found 4/24![British Airways logo]()
$780
This BusinessClass deal was found by Cheapflights users on 4/25. 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.
Tue 7/216:50 am
NAP
- ORD
2 stops21h 07m
Iberia
Tue 8/115:25 pm
ORD
- NAP
Nonstop9h 35m
Iberia
Deal found 4/25![Iberia logo]()
$811
This Delta deal was found by Cheapflights users on 4/25. 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 6/96:05 am
NAP
- MDW
2 stops19h 26m
Delta
Tue 6/166:05 am
MDW
- NAP
2 stops19h 05m
Delta
Deal found 4/25![Delta logo]()
$716
This KLM deal was found by Cheapflights users on 4/26. 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.
Fri 6/126:05 am
NAP
- MDW
2 stops19h 26m
Multiple Airlines
Tue 6/1611:05 am
MDW
- NAP
1 stop13h 00m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$717
This KLM deal was found by Cheapflights users on 4/27. 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 5/2312:45 pm
NAP
- ORD
1 stop32h 30m
KLM
Fri 5/296:06 pm
ORD
- NAP
1 stop29h 59m
KLM
Deal found 4/27![KLM logo]()
$732
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 6/126:05 am
NAP
- ORD
2 stops19h 24m
Delta
Tue 6/169:48 am
ORD
- NAP
1 stop14h 17m
Delta
Deal found 4/26![Delta logo]()
$717
This Delta deal was found by Cheapflights users on 4/24. 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 5/186:05 am
NAP
- ORD
2 stops19h 00m
Delta
Mon 5/256:07 am
ORD
- NAP
1 stop19h 03m
Delta
Deal found 4/24![Delta logo]()
$793
This Finnair deal was found by Cheapflights users on 4/24. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/810:35 am
NAP
- ORD
1 stop14h 15m
Multiple Airlines
Mon 6/154:55 pm
ORD
- NAP
1 stop22h 50m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$879
This Delta deal was found by Cheapflights users on 4/27. 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
NAP
- MDW
2 stops19h 26m
Delta
Fri 10/26:00 am
MDW
- NAP
2 stops19h 10m
Delta
Deal found 4/27![Delta logo]()
$797
This KLM deal was found by Cheapflights users on 4/27. 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.
Fri 7/109:05 am
NAP
- MDW
1 stop20h 10m
Multiple Airlines
Tue 8/41:16 pm
MDW
- NAP
2 stops15h 14m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$997
This Delta deal was found by Cheapflights users on 4/27. 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
NAP
- ORD
2 stops22h 31m
Delta
Fri 10/26:10 pm
ORD
- NAP
2 stops17h 05m
Delta
Deal found 4/27![Delta logo]()
$860
This KLM deal was found by Cheapflights users on 4/27. 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.
Tue 7/146:05 am
NAP
- MDW
2 stops23h 10m
Multiple Airlines
Tue 8/41:49 pm
MDW
- NAP
2 stops14h 41m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$1,001
This Delta deal was found by Cheapflights users on 4/23. 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 6/76:05 am
NAP
- ORD
2 stops22h 52m
Delta
Sun 6/145:30 am
ORD
- NAP
1 stop18h 35m
Delta
Deal found 4/23![Delta logo]()
$890
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 6/126:05 am
NAP
- MDW
2 stops19h 26m
Delta
Sun 6/289:54 am
MDW
- NAP
2 stops18h 36m
Delta
Deal found 4/25![Delta logo]()
$901
This Delta deal was found by Cheapflights users on 4/23. 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 5/186:05 am
NAP
- MDW
2 stops19h 28m
Delta
Mon 5/256:23 am
MDW
- NAP
2 stops18h 47m
Delta
Deal found 4/23![Delta logo]()
$943
Last-minute flights from Naples to ChicagoDiscover last-minute flight deals from Naples to Chicago. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Naples to Chicago. Data last updated April 28, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 4/25. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
Finnair
Mon 5/255:30 pm
ORD
- NAP
Nonstop9h 30m
Finnair
Deal found 4/25![Finnair logo]()
$580
This lol.travel deal was found by Cheapflights users on 4/24. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
British Airways
Mon 5/257:05 pm
ORD
- NAP
1 stop12h 25m
British Airways
Deal found 4/24![British Airways logo]()
$613
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
American Airlines
Mon 5/257:05 pm
ORD
- NAP
1 stop19h 55m
American Airlines
Deal found 4/23![American Airlines logo]()
$625
This Iberia deal was found by Cheapflights users on 4/27. 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.
Mon 5/183:00 pm
NAP
- ORD
Nonstop10h 55m
Multiple Airlines
Mon 5/258:50 pm
ORD
- NAP
1 stop18h 10m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$626
This Delta deal was found by Cheapflights users on 4/27. 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 5/186:05 am
NAP
- MDW
2 stops19h 28m
Delta
Mon 5/259:23 am
MDW
- NAP
2 stops19h 07m
Delta
Deal found 4/27![Delta logo]()
$887
This lol.travel deal was found by Cheapflights users on 4/24. 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.
Thu 5/213:00 pm
NAP
- ORD
Nonstop10h 55m
Finnair
Mon 5/255:30 pm
ORD
- NAP
Nonstop9h 30m
Finnair
Deal found 4/24![Finnair logo]()
$586
This lol.travel deal was found by Cheapflights users on 4/24. 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.
Thu 5/213:00 pm
NAP
- ORD
Nonstop10h 55m
British Airways
Mon 5/257:05 pm
ORD
- NAP
1 stop12h 25m
British Airways
Deal found 4/24![British Airways logo]()
$620
This Delta deal was found by Cheapflights users on 4/24. 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 5/216:05 am
NAP
- MDW
2 stops22h 04m
Delta
Mon 5/256:23 am
MDW
- NAP
2 stops18h 47m
Delta
Deal found 4/24![Delta logo]()
$1,013
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 5/226:05 am
NAP
- MDW
2 stops19h 28m
Delta
Thu 5/286:23 am
MDW
- NAP
2 stops18h 47m
Delta
Deal found 4/26![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 4/27. 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 5/236:05 am
NAP
- MDW
2 stops18h 51m
Delta
Fri 5/291:59 pm
MDW
- NAP
2 stops14h 31m
Delta
Deal found 4/27![Delta logo]()
$735
This Delta deal was found by Cheapflights users on 4/26. 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 5/266:05 am
NAP
- MDW
2 stops19h 28m
Delta
Tue 6/29:22 am
MDW
- NAP
2 stops19h 08m
Delta
Deal found 4/26![Delta logo]()
$988
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 5/296:05 am
NAP
- MDW
2 stops19h 28m
Delta
Thu 6/49:23 am
MDW
- NAP
2 stops19h 07m
Delta
Deal found 4/26![Delta logo]()
$836
One-way flights from Naples to ChicagoSearch for one-way flight options from Naples to Chicago. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
Search for one-way flight options from Naples to Chicago. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 9/299:10 pm
NAP
- ORD
3 stops41h 51m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 10/132:00 pm
NAP
- ORD
3 stops49h 01m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 9/210:50 am
NAP
- ORD
3 stops38h 00m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/207:45 am
NAP
- ORD
3 stops39h 55m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 10/147:45 am
NAP
- ORD
3 stops41h 30m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 9/308:15 am
NAP
- ORD
3 stops40h 35m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 10/109:50 am
NAP
- ORD
3 stops39h 00m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 10/211:55 pm
NAP
- ORD
3 stops34h 55m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/277:45 am
NAP
- ORD
3 stops39h 55m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$421
This deal was found by Cheapflights users on 4/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:40 am
NAP
- ORD
1 stop15h 15m
British Airways
Deal found 4/26![British Airways logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 9/210:05 am
NAP
- MDW
3 stops43h 06m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/217:15 pm
NAP
- MDW
3 stops57h 47m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$625
Find flight deals from Naples to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Naples (NAP) to Chicago (CHI). 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 April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $570 (lol.travel) |
One-way from | $374 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $675 |
Good one-way deal | $591 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Naples to Chicago 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 April 28, 2026.
Use the filters below to find and compare flights from Naples to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 5/18
3:00 pm-6:55 pm
Nonstop10h 55m
Chicago O'Hare Intl
Mon 5/25
5:30 pm-10:00 am
Nonstop9h 30m
$634
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 5/18
3:00 pm-6:55 pm
Nonstop10h 55m
Chicago O'Hare Intl
Mon 5/25
5:30 pm-10:00 am
Nonstop9h 30m
$636
NaplesChicago
NAP - MDW
NAPMDW
Naples
Fri 6/12
6:05 am-6:31 pm
2 stops19h 26m
Chicago Midway
Tue 6/16
6:05 am-8:10 am
2 stops19h 05m
$682
NaplesChicago
NAP - ORD
NAPORD
Naples
Fri 6/12
6:05 am-3:10 pm
1 stop16h 05m
Chicago O'Hare Intl
Tue 6/16
9:48 am-7:05 am
1 stop14h 17m
$712
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 6/9
10:15 am-9:48 pm
1 stop18h 33m
Chicago O'Hare Intl
Tue 6/16
6:05 am-8:10 am
1 stop19h 05m
$712
NaplesChicago
NAP - MDW
NAPMDW
Naples
Tue 6/9
6:05 am-6:31 pm
2 stops19h 26m
Chicago Midway
Tue 6/16
6:05 am-8:10 am
2 stops19h 05m
$716
NaplesChicago
NAP - MDW
NAPMDW
Naples
Fri 6/12
6:05 am-6:31 pm
2 stops19h 26m
Chicago Midway
Tue 6/16
11:05 am-7:05 am
1 stop13h 00m
$717
NaplesChicago
NAP - ORD
NAPORD
Naples
Fri 6/12
6:05 am-6:29 pm
2 stops19h 24m
Chicago O'Hare Intl
Tue 6/16
9:48 am-7:05 am
1 stop14h 17m
$717
NaplesChicago
NAP - ORD
NAPORD
Naples
Sat 5/23
12:45 pm-2:15 pm
1 stop32h 30m
Chicago O'Hare Intl
Fri 5/29
6:06 pm-7:05 am
1 stop29h 59m
$732
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 5/18
7:40 am-6:15 pm
1 stop17h 35m
Chicago O'Hare Intl
Mon 5/25
7:05 pm-10:00 pm
1 stop19h 55m
$780
Showing 1-10 of 38 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Naples-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Naples-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Naples-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Naples-Chicago 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 Naples-Chicago 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 Naples to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Naples with our price prediction graph.
NAP-CHI
NAP-ORD
NAP-MDW
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 Naples to Chicago
NAP-CHI
NAP-ORD
NAP-MDW
What is the cheapest month to book a flight from Naples to Chicago?
Currently, November is the cheapest month in which you can book a flight from Naples to Chicago (average of $481). Flying from Naples to Chicago in March is currently the most expensive (average of $728). 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.
How often are flights from Naples to Chicago delayed?
About 23% of weekly flights between Naples and Chicago have experienced delays in the past year, with the average delay time being 222 minutes.
What is the most punctual flight time for Naples to Chicago flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning 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 Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Naples to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 23% of flights being delayed.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 28, 2026.
See what other customers who have flown with Turkish Airlines and American Airlines from Naples to Chicago 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
Food
7.5
Overall
7.4
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Food
7.5
Overall
7.4
Crew
7.8
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Boarding
7.3
Comfort
7.3
Food
7.5
Overall
7.4
Crew
7.8
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 Naples to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
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Naples and Chicago flights
Browse other Naples and Chicago flight options. Last updated on April 28, 2026.
Other flights from Naples
Browse through other flights departing from Naples. Flights are based on user searches made on Cheapflights and were last updated on April 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Naples to Chicago
Discover the top airline that operate flights from Naples to Chicago. 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 April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$639 | Average$738 | FlexibilityNo cancel fee | On-time71% |