$379+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Nov 24 — Dec 11
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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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 October 25, 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 October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 12/36:00 am -
1 stop15h 55m
Mon 12/75:40 pm -
1 stop13h 40m
Deal found 10/21![American Airlines logo]()
$636
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 12/36:00 am -
1 stop15h 55m
Mon 12/75:40 pm -
1 stop13h 40m
Deal found 10/21![Multiple Airlines logo]()
$637
This Iberia deal was found by Cheapflights users on 10/20. 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.
Thu 12/36:00 am -
2 stops24h 00m
Mon 12/71:30 pm -
2 stops17h 50m
Deal found 10/20![Iberia logo]()
$641
This Expedia deal was found by Cheapflights users on 10/20. 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.
Fri 12/46:00 am -
1 stop15h 55m
Fri 12/111:30 pm -
2 stops26h 00m
Deal found 10/20![Iberia logo]()
$642
This Expedia deal was found by Cheapflights users on 10/21. 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.
Thu 12/311:20 am -
2 stops19h 36m
Mon 12/76:25 pm -
1 stop19h 45m
Deal found 10/21![KLM logo]()
$654
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 October 25, 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 October 25, 2026.
This British Airways deal was found by Cheapflights users on 10/21. 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 1/1411:40 am -
1 stop33h 05m
Mon 1/189:48 pm -
2 stops53h 57m
Deal found 10/21![British Airways logo]()
$643
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Thu 12/36:00 am -
1 stop15h 55m
Mon 12/75:40 pm -
1 stop13h 40m
Deal found 10/25![Multiple Airlines logo]()
$646
This Delta deal was found by Cheapflights users on 10/25. 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 12/46:10 am -
1 stop17h 05m
Wed 12/910:38 am -
2 stops22h 12m
Deal found 10/25![Delta logo]()
$654
This Ovago deal was found by Cheapflights users on 10/23. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 am -
2 stops23h 30m
Mon 12/141:30 pm -
2 stops17h 50m
Deal found 10/23![Iberia logo]()
$682
This Expedia deal was found by Cheapflights users on 10/24. 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 Expedia is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Thu 12/311:20 am -
2 stops19h 36m
Mon 12/73:59 pm -
2 stops15h 16m
Deal found 10/24![KLM logo]()
$687
Last-minute flights from Naples to ChicagoDiscover last-minute flight deals from Naples to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Naples to Chicago. Data last updated October 25, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 10/22. 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.
Thu 10/228:50 pm -
1 stop19h 50m
Mon 10/269:15 pm -
1 stop15h 20m
Deal found 10/22![Turkish Airlines logo]()
$987
This ITA Airways deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:35 am -
1 stop13h 35m
Tue 10/2710:32 am -
2 stops18h 03m
Deal found 10/22![ITA Airways logo]()
$856
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 10/248:50 pm -
1 stop21h 10m
Wed 10/288:00 pm -
2 stops36h 50m
Deal found 10/22![Multiple Airlines logo]()
$992
This Booking.com deal was found by Cheapflights users on 10/22. 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 10/257:35 pm -
1 stop21h 25m
Fri 10/3012:45 pm -
1 stop23h 50m
Deal found 10/22![Turkish Airlines logo]()
$891
This Iberia deal was found by Cheapflights users on 10/21. 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.
Thu 10/299:50 am -
2 stops39h 55m
Wed 1/275:40 pm -
1 stop13h 40m
Deal found 10/21![Iberia logo]()
$910
This Iberia deal was found by Cheapflights users on 10/21. 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.
Thu 10/299:50 am -
2 stops39h 55m
Thu 1/288:40 pm -
2 stops34h 40m
Deal found 10/21![Iberia logo]()
$913
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/2911:20 am -
2 stops23h 55m
Tue 1/269:50 pm -
1 stop12h 55m
Deal found 10/21![Multiple Airlines logo]()
$991
This Delta deal was found by Cheapflights users on 10/21. 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 10/3111:50 am -
1 stop33h 35m
Mon 1/256:25 pm -
1 stop19h 45m
Deal found 10/21![Delta logo]()
$853
This Delta deal was found by Cheapflights users on 10/21. 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 10/3111:50 am -
1 stop33h 35m
Sun 1/3110:40 am -
2 stops22h 10m
Deal found 10/21![Delta logo]()
$854
This Delta deal was found by Cheapflights users on 10/22. 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 10/3111:50 am -
1 stop33h 35m
Tue 1/266:25 pm -
1 stop14h 25m
Deal found 10/22![Delta logo]()
$876
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 October 25, 2026.
Search for one-way flight options from Naples to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Expedia deal was found by Cheapflights users on 10/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2910:35 am -
1 stop14h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Finnair logo]()
$379
This Expedia deal was found by Cheapflights users on 10/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/306:45 am -
2 stops22h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Iberia logo]()
$406
This British Airways deal was found by Cheapflights users on 10/24. 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.
Tue 3/3012:55 pm -
1 stop31h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![British Airways logo]()
$420
This British Airways deal was found by Cheapflights users on 10/24. 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.
Tue 3/307:40 am -
2 stops19h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$425
This Expedia deal was found by Cheapflights users on 10/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2911:40 am -
2 stops29h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$497
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/286:40 am -
2 stops18h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$531
This CheapOair deal was found by Cheapflights users on 10/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/289:25 am -
1 stop15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Turkish Airlines logo]()
$578
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $636 (American Airlines) |
One-way from | $379 (Expedia) |
Popular in | September |
Cheapest in | October |
Average price | $693 |
Good round-trip deal | $1,061 or less |
Good one-way deal | $854 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 October 25, 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 Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Mon 3/29
10:35 am-5:50 pm
1 stop14h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$379
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Tue 3/30
7:40 am-7:59 pm
2 stops19h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$425
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Mon 3/29
5:50 pm-6:15 pm
3 stops31h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$497
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Mon 12/28
9:25 am-6:20 pm
1 stop15h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$578
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Mon 12/28
10:15 pm-6:20 pm
1 stop27h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$610
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Thu 1/14
11:40 am-1:45 pm
1 stop33h 05m
Chicago O'Hare Intl
Mon 1/18
9:48 pm-10:45 am
2 stops53h 57m
$643
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Thu 12/3
6:00 am-2:55 pm
1 stop15h 55m
Chicago O'Hare Intl
Mon 12/7
5:40 pm-2:20 pm
1 stop13h 40m
$646
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Fri 12/4
6:10 am-4:15 pm
1 stop17h 05m
Chicago O'Hare Intl
Wed 12/9
10:38 am-3:50 pm
2 stops22h 12m
$654
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Mon 12/7
6:00 am-10:30 pm
2 stops23h 30m
Chicago O'Hare Intl
Mon 12/14
1:30 pm-2:20 pm
2 stops17h 50m
$682
NaplesChicago
NAP Naples - ORD Chicago O'Hare Intl
NAPORD
Naples
Thu 12/3
11:20 am-11:56 pm
2 stops19h 36m
Chicago O'Hare Intl
Mon 12/7
3:59 pm-2:15 pm
2 stops15h 16m
$687
Showing 1-10 of 11 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star |
- 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
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
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 October 25, 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 13% of weekly flights between Naples and Chicago have experienced delays in the past year, with the average delay time being 232 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?
Wednesday 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 13% 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 October 25, 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
Overall
7.4
Comfort
7.3
Boarding
7.3
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
Food
7.5
Overall
7.4
Comfort
7.3
Boarding
7.3
Entertainment
7.5
Crew
7.8
Reviews
1 / 20
2.0
MediocreGigi,Oct 2026
IST - MIA
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
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Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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