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$285+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
feb. 14 — feb. 211
sáb. 2/14
sáb. 2/21
1 adult, Economy
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Cheap 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 enero 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$584
(Mytrip)

One-way from

$285
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$606

Good round-trip deal

$757 or less

Good one-way deal

$491 or less
Provider with most accurate pricing for Naples-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Naples-Chicago (CHI) flights.
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From Naples to Chicago (CHI)
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One-way flight from Naples to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($89 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Naples to Chicago (CHI).
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Price to beat on a one-way flight from Naples to Chicago (CHI).
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Find flight deals from Naples to Chicago

Cheapest flights from Naples to Chicago
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 enero 15, 2026.

This deal was found by Cheapflights users on 1/13. 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.
lun. 8/243:00 pm
NAP
-
ORD
Nonstop10h 50m
American Airlines
mié. 9/25:25 pm
ORD
-
NAP
Nonstop9h 35m
American Airlines
Deal found 1/13$525
This deal was found by Cheapflights users on 1/13. 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.
lun. 8/243:00 pm
NAP
-
ORD
Nonstop10h 50m
American Airlines
dom. 8/305:25 pm
ORD
-
NAP
Nonstop9h 35m
American Airlines
Deal found 1/13$564
This Mytrip deal was found by Cheapflights users on 1/13. 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.
lun. 3/26:00 am
NAP
-
ORD
2 stops21h 05m
Multiple Airlines
dom. 3/87:50 pm
ORD
-
NAP
2 stops20h 50m
Multiple Airlines
Deal found 1/13$584
This lol.travel deal was found by Cheapflights users on 1/15. 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.
lun. 3/21:55 pm
NAP
-
ORD
1 stop32h 30m
British Airways
dom. 3/810:45 pm
ORD
-
NAP
1 stop31h 05m
British Airways
Deal found 1/15$595
This American Airlines deal was found by Cheapflights users on 1/15. 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.
lun. 3/21:55 pm
NAP
-
ORD
1 stop32h 30m
American Airlines
dom. 3/89:35 pm
ORD
-
NAP
1 stop32h 15m
American Airlines
Deal found 1/15$609
This American Airlines deal was found by Cheapflights users on 1/15. 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.
vie. 2/136:20 am
NAP
-
ORD
1 stop15h 35m
American Airlines
vie. 2/206:30 pm
ORD
-
NAP
1 stop34h 15m
American Airlines
Deal found 1/15$612
This Iberia deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/76:15 am
NAP
-
ORD
1 stop15h 40m
Multiple Airlines
dom. 2/155:10 pm
ORD
-
NAP
1 stop12h 55m
Multiple Airlines
Deal found 1/12$613
This Iberia deal was found by Cheapflights users on 1/13. 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.
sáb. 1/246:15 am
NAP
-
ORD
1 stop15h 40m
Multiple Airlines
dom. 2/16:25 pm
ORD
-
NAP
1 stop11h 40m
Multiple Airlines
Deal found 1/13$615
This Delta deal was found by Cheapflights users on 1/15. 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.
mar. 3/106:15 am
NAP
-
MDW
2 stops17h 39m
Delta
mar. 3/171:10 pm
MDW
-
NAP
2 stops20h 40m
Delta
Deal found 1/15$653
This Delta deal was found by Cheapflights users on 1/15. 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.
dom. 3/16:15 am
NAP
-
MDW
2 stops18h 22m
Delta
dom. 3/86:34 pm
MDW
-
NAP
2 stops20h 41m
Delta
Deal found 1/15$665
This Delta deal was found by Cheapflights users on 1/13. 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.
lun. 3/26:15 am
NAP
-
MDW
2 stops18h 22m
Delta
dom. 3/86:34 pm
MDW
-
NAP
2 stops20h 41m
Delta
Deal found 1/13$666
This Delta deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/76:15 am
NAP
-
MDW
2 stops17h 01m
Delta
dom. 2/151:29 pm
MDW
-
NAP
2 stops15h 01m
Delta
Deal found 1/12$667

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 enero 15, 2026.
Use the filters below to find and compare flights from Naples to Chicago that are best for you.

Fly from

Naples

Fly to

Chicago

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

lun. 3/2

1:55 pm-3:25 pm

1 stop32h 30m

Chicago O'Hare Intl

dom. 3/8

10:45 pm-11:50 am

1 stop31h 05m

$595

NaplesChicago

NAP - ORD

NAPORD

Naples

lun. 3/2

1:55 pm-3:25 pm

1 stop32h 30m

Chicago O'Hare Intl

dom. 3/8

9:35 pm-11:50 am

1 stop32h 15m

$609

NaplesChicago

NAP - ORD

NAPORD

Naples

vie. 2/13

6:20 am-2:55 pm

1 stop15h 35m

Chicago O'Hare Intl

vie. 2/20

6:30 pm-11:45 am

1 stop34h 15m

$612

NaplesChicago

NAP - ORD

NAPORD

Naples

dom. 3/1

3:00 pm-4:20 pm

1 stop32h 20m

Chicago O'Hare Intl

dom. 3/8

7:50 pm-2:10 pm

1 stop12h 20m

$615

NaplesChicago

NAP - ORD

NAPORD

Naples

jue. 1/29

3:05 pm-4:20 pm

1 stop32h 15m

Chicago O'Hare Intl

mié. 2/4

6:50 pm-9:15 am

1 stop31h 25m

$617

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 2/7

10:00 am-4:20 pm

1 stop13h 20m

Chicago O'Hare Intl

dom. 2/15

6:50 pm-2:10 pm

1 stop12h 20m

$618

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 2/7

6:15 am-7:50 am

2 stops32h 35m

Chicago O'Hare Intl

dom. 2/15

6:08 am-1:05 pm

2 stops23h 57m

$619

NaplesChicago

NAP - ORD

NAPORD

Naples

mar. 3/10

2:50 pm-5:20 pm

1 stop32h 30m

Chicago O'Hare Intl

mar. 3/17

10:50 pm-5:25 pm

1 stop12h 35m

$620

NaplesChicago

NAP - MDW

NAPMDW

Naples

mar. 3/10

6:15 am-5:54 pm

2 stops17h 39m

Chicago Midway

mar. 3/17

1:10 pm-3:50 pm

2 stops20h 40m

$653

NaplesChicago

NAP - MDW

NAPMDW

Naples

lun. 3/2

6:15 am-6:40 pm

2 stops19h 25m

Chicago Midway

dom. 3/8

6:34 pm-9:15 pm

2 stops20h 41m

$665

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 36 results
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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 January.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Naples-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Naples-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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

How much does it cost to fly round-trip from Naples to Chicago?

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 enero 15, 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.
Turkish Airlines
7.3
Good
4,175 reviews

Entertainment

7.4

Boarding

7.3

Comfort

7.3

Crew

7.8

Overall

7.3

Food

7.4

Reviews

1 / 20
2.0
Mediocre

Joel,Nov 2025

IST - IAD

The flight was fine except half the bathrooms in economy class were out of order and taped shut. Turkish Airlines had changed or ultimately canceled the flight to Istanbul several times and the vendor that kayak uses to purchase the tickets then canceled our reservations without informing us. When I called for a boarding pass 24 hours before the flight, we found out that our reservations have been canceled and had to act quickly to get new reservations at double the expense… Using the same vendor who had gotten reimbursed for the original flights.
Turkish Airlines
7.3
Good
4,175 reviews
Turkish Airlines
7.3
Good
4,175 reviews

Entertainment

7.4

Boarding

7.3

Comfort

7.3

Crew

7.8

Overall

7.3

Food

7.4

Reviews

1 / 20
2.0
Mediocre

Joel,Nov 2025

IST - IAD

The flight was fine except half the bathrooms in economy class were out of order and taped shut. Turkish Airlines had changed or ultimately canceled the flight to Istanbul several times and the vendor that kayak uses to purchase the tickets then canceled our reservations without informing us. When I called for a boarding pass 24 hours before the flight, we found out that our reservations have been canceled and had to act quickly to get new reservations at double the expense… Using the same vendor who had gotten reimbursed for the original flights.
American Airlines
7.2
Good
11,135 reviews
Turkish Airlines
7.3
Good
4,175 reviews

Entertainment

7.4

Boarding

7.3

Comfort

7.3

Crew

7.8

Overall

7.3

Food

7.4

Reviews

1 / 20
2.0
Mediocre

Joel,Nov 2025

IST - IAD

The flight was fine except half the bathrooms in economy class were out of order and taped shut. Turkish Airlines had changed or ultimately canceled the flight to Istanbul several times and the vendor that kayak uses to purchase the tickets then canceled our reservations without informing us. When I called for a boarding pass 24 hours before the flight, we found out that our reservations have been canceled and had to act quickly to get new reservations at double the expense… Using the same vendor who had gotten reimbursed for the original flights.

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.

  • What airport do you fly from for flights from Naples to Chicago?

    Located just 2.9 mi from the city center, Naples is the airport most travelers will use when flying to Chicago from Naples. Booking flights from Naples (NAP) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 1 airline.

  • How long is the flight from Naples to Chicago?

    There are many flights that can get you from Naples to Chicago in 17h 39m. Fly via British Airways, American Airlines, or Delta to get the fastest option. There are 4931 mi between Naples and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Naples to Chicago round-trip?

    According to our current data, American Airlines ($664), offers the cheapest pricing from Naples to Chicago. Users have found that American Airlines is 8% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Naples to Chicago one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $396. Aer Lingus flights start at $471 while deals on Turkish Airlines start at $484 one-way.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $448. On average you can expect to pay $649. The most popular route, (Naples - Chicago O'Hare Intl), can usually be booked for $450.

  • Can I find deals for flights from Naples to Chicago that include hotel bookings?

    Yes. In addition to deals on Naples to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Naples to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Naples to Chicago.

  • Can I find deals for business class flights from Naples to Chicago?

    Yes. Cheapflights offers flight deals from Naples to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Naples to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Naples to O'Hare Intl flights

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 enero 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$664Average$877FlexibilityNo cancel feeOn-time71%

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