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$304+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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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 November 12, 2025.

This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:20 amNAP - ORD
1 stop15h 35mAmerican Airlines
Sun 11/308:40 pmORD - NAP
1 stop32h 10mAmerican Airlines
Deal found 11/10$608
This KLM deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:50 amNAP - ORD
1 stop33h 30mKLM
Wed 12/101:23 pmORD - NAP
2 stops14h 47mKLM
Deal found 11/10$620
This Delta deal was found by Cheapflights users on 11/12. 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.
Fri 12/56:15 amNAP - ORD
1 stop15h 55mDelta
Tue 12/95:20 pmORD - NAP
1 stop20h 55mDelta
Deal found 11/12$621
This Delta deal was found by Cheapflights users on 11/11. 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 12/56:15 amNAP - MDW
2 stops18h 45mDelta
Tue 12/91:50 pmMDW - NAP
2 stops19h 00mDelta
Deal found 11/11$625
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:50 amNAP - MDW
2 stops18h 57mDelta
Wed 12/109:59 amMDW - NAP
2 stops18h 11mDelta
Deal found 11/10$626
This KLM deal was found by Cheapflights users on 11/12. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:15 amNAP - ORD
1 stop15h 55mKLM
Wed 12/101:23 pmORD - NAP
2 stops14h 47mKLM
Deal found 11/12$638
This Delta deal was found by Cheapflights users on 11/12. 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.
Sat 12/611:50 amNAP - MDW
2 stops18h 57mDelta
Wed 12/101:14 pmMDW - NAP
2 stops14h 56mDelta
Deal found 11/12$638
This Air France deal was found by Cheapflights users on 11/12. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:45 pmNAP - ORD
1 stop29h 25mAir France
Tue 12/95:20 pmORD - NAP
1 stop20h 55mAir France
Deal found 11/12$644
This Delta deal was found by Cheapflights users on 11/12. 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.
Thu 12/411:50 amNAP - ORD
2 stops19h 11mDelta
Sun 12/76:45 amORD - NAP
2 stops21h 45mDelta
Deal found 11/12$649
This Trip.com deal was found by Cheapflights users on 11/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:15 amNAP - MDW
2 stops24h 32mAir France
Tue 12/91:50 pmMDW - NAP
2 stops19h 00mAir France
Deal found 11/12$652
This American Airlines deal was found by Cheapflights users on 11/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:20 amNAP - ORD
1 stop15h 35mAmerican Airlines
Sun 12/75:40 pmORD - NAP
1 stop13h 30mAmerican Airlines
Deal found 11/12$654
This Expedia deal was found by Cheapflights users on 11/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:35 amNAP - MDW
2 stops24h 12mKLM
Sun 12/71:05 pmMDW - NAP
2 stops18h 15mKLM
Deal found 11/12$656

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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$613
(American Airlines)

One-way from

$304
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$869

Good round-trip deal

$757 or less

Good one-way deal

$450 or less
Provider with most accurate pricing for Naples-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Naples-Chicago (CHI) flights.
Search Deals
From Naples to Chicago (CHI)
Search Deals
One-way flight from Naples to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Naples to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Naples to Chicago (CHI).
Search Deals

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 November 12, 2025.
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

Wed 2/18

6:20 am-6:45 pm

2 stops19h 25m

Chicago O'Hare Intl

Sun 2/22

3:20 pm-1:05 pm

2 stops14h 45m

$613

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 12/4

11:50 am-2:20 pm

1 stop33h 30m

Chicago O'Hare Intl

Wed 12/10

4:25 pm-11:10 am

1 stop11h 45m

$620

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 12/5

6:15 am-3:10 pm

1 stop15h 55m

Chicago O'Hare Intl

Tue 12/9

5:20 pm-9:15 pm

1 stop20h 55m

$621

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 12/5

6:15 am-6:00 pm

2 stops18h 45m

Chicago Midway

Tue 12/9

1:50 pm-3:50 pm

2 stops19h 00m

$625

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 1/16

4:40 pm-1:50 pm

1 stop28h 10m

Chicago O'Hare Intl

Thu 1/22

2:14 pm-3:35 pm

2 stops18h 21m

$626

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 12/4

11:50 am-11:47 pm

2 stops18h 57m

Chicago Midway

Wed 12/10

9:59 am-11:10 am

2 stops18h 11m

$626

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 2/10

6:15 am-10:26 pm

2 stops23h 11m

Chicago Midway

Sun 2/15

11:00 am-11:30 am

2 stops17h 30m

$626

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 2/18

9:50 am-4:20 pm

1 stop13h 30m

Chicago O'Hare Intl

Sun 2/22

4:10 pm-2:10 pm

1 stop15h 00m

$629

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 1/16

6:15 am-10:09 pm

2 stops22h 54m

Chicago Midway

Thu 1/22

1:28 pm-3:50 pm

2 stops19h 22m

$638

NaplesChicago

NAP - MDW

NAPMDW

Naples

Sat 12/6

11:50 am-11:47 pm

2 stops18h 57m

Chicago Midway

Wed 12/10

1:14 pm-11:10 am

2 stops14h 56m

$638

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 26 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 November.
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
No data available for this route at this time. Please check back soon.

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 November 12, 2025.
See what other customers who have flown with 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.
American Airlines
7.2
Good
11,050 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 15h 55m. Fly via American Airlines, KLM, or Delta to get the fastest option. There are 4929 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 2% cheaper than the other options available to this destination.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $417. On average you can expect to pay $706. The most popular route, (Naples - Chicago Midway), can usually be booked for $625.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$664Average$877FlexibilityNo cancel feeOn-time71%

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