$373+ Cheap flights from Naples (NAP) to Chicago (CHI)
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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Oct 7 — Oct 141
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
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.Cheap flight deals from Naples to Chicago
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Best
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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 September 7, 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 September 7, 2026.
This lol.travel deal was found by Cheapflights users on 9/3. 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 10/157:35 pm -
1 stop24h 35m
Fri 10/233:00 pm -
1 stop16h 20m
Deal found 9/3![ITA Airways logo]()
$582
This lol.travel deal was found by Cheapflights users on 9/3. 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 10/510:35 am -
1 stop14h 15m
Sun 10/115:25 pm -
Nonstop9h 35m
Deal found 9/3![Finnair logo]()
$593
This lol.travel deal was found by Cheapflights users on 9/2. 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.
Fri 10/23:00 pm -
Nonstop10h 55m
Tue 10/65:25 pm -
Nonstop9h 35m
Deal found 9/2![Finnair logo]()
$596
This lol.travel deal was found by Cheapflights users on 9/4. 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 10/153:00 pm -
Nonstop10h 50m
Mon 10/195:25 pm -
Nonstop9h 35m
Deal found 9/4![Finnair logo]()
$597
This Trip.com deal was found by Cheapflights users on 9/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:35 am -
1 stop13h 35m
Fri 10/233:00 pm -
1 stop12h 35m
Deal found 9/4![ITA Airways logo]()
$625
This lol.travel deal was found by Cheapflights users on 9/3. 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.
Fri 10/23:00 pm -
Nonstop10h 55m
Tue 10/69:15 pm -
1 stop13h 50m
Deal found 9/3![British Airways logo]()
$628
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:00 pm -
Nonstop10h 50m
Mon 10/1210:30 pm -
2 stops40h 30m
Deal found 9/7![British Airways logo]()
$632
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 pm -
1 stop27h 55m
Sun 10/49:15 pm -
1 stop15h 20m
Deal found 9/7![British Airways logo]()
$634
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.
Tue 9/223:00 pm -
Nonstop10h 55m
Sat 9/2610:15 pm -
2 stops38h 20m
Deal found 9/6![British Airways logo]()
$635
This Delta deal was found by Cheapflights users on 9/3. 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 10/66:05 am -
2 stops18h 55m
Tue 10/2010:12 am -
2 stops18h 18m
Deal found 9/3![Delta logo]()
$667
This Expedia deal was found by Cheapflights users on 9/4. 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.
Mon 10/56:05 am -
2 stops23h 39m
Sun 10/1110:59 am -
1 stop13h 06m
Deal found 9/4![Air France logo]()
$673
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 9/306:05 am -
2 stops19h 28m
Sun 10/46:05 am -
1 stop18h 00m
Deal found 9/7![Delta logo]()
$674
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 September 7, 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 September 7, 2026.
This Delta deal was found by Cheapflights users on 9/3. 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 10/66:05 am -
1 stop16h 05m
Tue 10/206:00 pm -
2 stops17h 15m
Deal found 9/3![Delta logo]()
$662
This KLM deal was found by Cheapflights users on 9/3. 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 10/66:05 am -
1 stop16h 05m
Tue 10/205:10 pm -
1 stop18h 05m
Deal found 9/3![KLM logo]()
$662
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:00 pm -
Nonstop10h 55m
Mon 9/215:35 pm -
Nonstop9h 25m
Deal found 9/6![British Airways logo]()
$665
This Delta deal was found by Cheapflights users on 9/3. 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 10/66:05 am -
2 stops18h 55m
Tue 10/2010:12 am -
2 stops18h 18m
Deal found 9/3![Delta logo]()
$667
This British Airways deal was found by Cheapflights users on 9/2. 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.
Thu 10/18:00 pm -
1 stop26h 55m
Mon 10/55:00 pm -
1 stop12h 00m
Deal found 9/2![British Airways logo]()
$669
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:05 am -
2 stops17h 09m
Mon 10/125:31 pm -
2 stops14h 49m
Deal found 9/6![KLM logo]()
$757
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:05 am -
2 stops18h 55m
Mon 10/1912:49 pm -
2 stops15h 41m
Deal found 9/5![Delta logo]()
$751
Last-minute flights from Naples to ChicagoDiscover last-minute flight deals from Naples to Chicago. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Naples to Chicago. Data last updated September 7, 2026 and is based on user searches.
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:35 am -
2 stops17h 22m
Thu 9/176:05 am -
1 stop18h 00m
Deal found 9/7![KLM logo]()
$1,056
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.
Sat 9/126:05 am -
2 stops17h 52m
Thu 9/171:00 pm -
2 stops15h 30m
Deal found 9/7![Delta logo]()
$1,658
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.
Tue 9/223:00 pm -
Nonstop10h 55m
Sat 9/2610:15 pm -
2 stops38h 20m
Deal found 9/6![British Airways logo]()
$635
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 pm -
1 stop27h 55m
Sun 10/49:15 pm -
1 stop15h 20m
Deal found 9/7![British Airways logo]()
$634
This lol.travel deal was found by Cheapflights users on 9/2. 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.
Fri 10/23:00 pm -
Nonstop10h 55m
Tue 10/65:25 pm -
Nonstop9h 35m
Deal found 9/2![Finnair logo]()
$596
This lol.travel deal was found by Cheapflights users on 9/3. 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.
Fri 10/23:00 pm -
Nonstop10h 55m
Tue 10/69:15 pm -
1 stop13h 50m
Deal found 9/3![British Airways logo]()
$628
This lol.travel deal was found by Cheapflights users on 9/3. 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 10/510:35 am -
1 stop14h 15m
Sun 10/115:25 pm -
Nonstop9h 35m
Deal found 9/3![Finnair logo]()
$593
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:00 pm -
Nonstop10h 50m
Mon 10/1210:30 pm -
2 stops40h 30m
Deal found 9/7![British Airways logo]()
$632
This lol.travel deal was found by Cheapflights users on 9/3. 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 10/157:35 pm -
1 stop24h 35m
Fri 10/233:00 pm -
1 stop16h 20m
Deal found 9/3![ITA Airways logo]()
$582
This lol.travel deal was found by Cheapflights users on 9/4. 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 10/153:00 pm -
Nonstop10h 50m
Mon 10/195:25 pm -
Nonstop9h 35m
Deal found 9/4![Finnair logo]()
$597
This Trip.com deal was found by Cheapflights users on 9/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:35 am -
1 stop13h 35m
Fri 10/233:00 pm -
1 stop12h 35m
Deal found 9/4![ITA Airways logo]()
$625
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 September 7, 2026.
Search for one-way flight options from Naples to Chicago. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/2810:50 am -
3 stops37h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/275:35 pm -
3 stops55h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 3/14:40 pm -
2 stops31h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 12/37:55 am -
3 stops41h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 3/312:15 pm -
2 stops33h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$411
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/212:15 pm -
2 stops33h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 12/25:35 pm -
3 stops30h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 12/11:15 pm -
2 stops33h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$415
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.
Sun 12/67:50 am -
3 stops40h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$417
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 10/59:50 pm -
2 stops44h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$498
This Delta deal was found by Cheapflights users on 9/3. 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 1/226:10 am -
2 stops19h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$523
This KLM deal was found by Cheapflights users on 9/4. 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.
Wed 10/2811:20 am -
2 stops17h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![KLM logo]()
$532
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $582 (lol.travel) |
One-way from | $373 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $641 |
Good round-trip deal | $843 or less |
Good one-way deal | $697 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 7,457,451 searches. Data last updated September 7, 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
NaplesChicago
NAP Naples - MDW Chicago Midway
NAPMDW
Naples
Mon 10/5
9:50 pm-11:00 am
2 stops44h 10m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$498
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Mon 3/1
6:10 am-4:15 pm
1 stop17h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$518
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Sun 12/6
6:10 am-4:15 pm
1 stop17h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$519
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Sat 12/5
1:40 pm-1:45 pm
1 stop31h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$528
NaplesChicago
NAP Naples - MDW Chicago Midway
NAPMDW
Naples
Wed 10/28
11:20 am-10:33 pm
2 stops17h 13m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$532
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Sat 11/7
6:25 pm-6:20 pm
3 stops54h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$570
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Fri 12/4
4:40 pm-1:45 pm
1 stop28h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$585
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Thu 10/1
11:40 am-2:00 pm
1 stop33h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$619
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Fri 10/30
9:20 am-11:00 am
1 stop31h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$625
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Wed 10/7
8:50 pm-9:40 am
1 stop19h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$625
Showing 1-10 of 26 resultsSorted by cheapest first
Compare providers for flights from Naples to Chicago
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 Naples to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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 time of day to fly from NAP to CHI?
Find hourly flight availability from Naples to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 7, 2026.
When flying from Naples to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Naples to Chicago delayed?
About 18% of weekly flights between Naples and Chicago have experienced delays in the past year, with the average delay time being 216 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?
Sunday tends to have the lowest number of delays on this route, whereas Tuesday 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 18% 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 September 7, 2026.
See what other customers who have flown with Turkish 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.
Food
7.5
Entertainment
7.5
Comfort
7.3
Overall
7.4
Boarding
7.3
Crew
7.8
Reviews
1 / 20
8.0
ExcellentMuhammad,Jan 2026
ORD - DFW
Food
7.5
Entertainment
7.5
Comfort
7.3
Overall
7.4
Boarding
7.3
Crew
7.8
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
Valparaiso
Hammond
Saint Joseph
Porter
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