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$449+ Cheap flights from Midway (MDW) to Naples (NAP)

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Midway to Naples

Cheapest flights from Midway to Naples
Explore the most affordable flight options available from Midway to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This KLM deal was found by Cheapflights users on 12/10. 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 12/259:29 amMDW - NAP
2 stops17h 16mKLM
Thu 1/156:15 amNAP - MDW
2 stops19h 17mKLM
Deal found 12/10$770
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:29 pmMDW - NAP
2 stops33h 16mKLM
Sun 12/1411:50 amNAP - MDW
2 stops18h 57mKLM
Deal found 12/10$1,161
This KLM deal was found by Cheapflights users on 12/10. 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 12/259:29 amMDW - NAP
2 stops17h 16mKLM
Mon 12/296:35 amNAP - MDW
2 stops17h 51mKLM
Deal found 12/10$1,261
This KLM deal was found by Cheapflights users on 12/9. 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 12/259:29 amMDW - NAP
2 stops17h 16mKLM
Wed 12/316:35 amNAP - MDW
2 stops17h 51mKLM
Deal found 12/9$1,377
This Delta deal was found by Cheapflights users on 12/9. 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 12/246:08 pmMDW - NAP
2 stops20h 07mDelta
Sun 12/286:15 amNAP - MDW
2 stops23h 07mDelta
Deal found 12/9$1,523
This Delta deal was found by Cheapflights users on 12/9. 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 12/246:08 pmMDW - NAP
2 stops20h 07mDelta
Mon 12/296:15 amNAP - MDW
2 stops23h 07mDelta
Deal found 12/9$1,524
This KLM deal was found by Cheapflights users on 12/9. 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 12/256:08 pmMDW - NAP
2 stops14h 42mMultiple Airlines
Tue 12/306:35 amNAP - MDW
2 stops17h 51mMultiple Airlines
Deal found 12/9$1,892
This Delta deal was found by Cheapflights users on 12/10. 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.
Tue 12/1612:50 pmMDW - NAP
2 stops20h 00mDelta
Sun 1/116:15 amNAP - MDW
2 stops22h 52mDelta
Deal found 12/10$2,007
This Delta deal was found by Cheapflights users on 12/11. 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 12/1210:49 amMDW - NAP
2 stops17h 21mDelta
Fri 12/196:15 amNAP - MDW
2 stops19h 03mDelta
Deal found 12/11$2,023
This Delta deal was found by Cheapflights users on 12/9. 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 12/249:50 amMDW - NAP
2 stops18h 20mDelta
Wed 12/316:15 amNAP - MDW
2 stops18h 04mDelta
Deal found 12/9$2,330
This Mytrip deal was found by Cheapflights users on 12/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2111:00 amMDW - NAP
3 stops25h 35mMultiple Airlines
Sun 12/288:10 amNAP - MDW
3 stops32h 55mMultiple Airlines
Deal found 12/11$2,408
This Air France deal was found by Cheapflights users on 12/9. 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.
Thu 12/256:08 pmMDW - NAP
2 stops14h 42mAir France
Thu 1/16:15 amNAP - MDW
2 stops18h 04mAir France
Deal found 12/9$2,424

Find flight deals from Midway to Naples

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Naples (NAP). 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$661
(KLM)

One-way from

$449
(Air France)

Popular in

June

Cheapest in

February

Average price

$932
Provider with most accurate pricing for Chicago Midway-Naples flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Naples flights.
Search Deals
From Chicago Midway to Naples
Search Deals
One-way flight from Chicago Midway to Naples
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($239 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Naples 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 December 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Naples that are best for you.

Fly from

Midway

Fly to

Naples

Route

Depart

Return

Price

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 1/7

9:32 am-9:15 pm

2 stops28h 43m

Naples

Thu 1/15

12:15 pm-5:37 pm

2 stops36h 22m

$770

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 12/25

9:29 am-9:45 am

2 stops17h 16m

Naples

Thu 1/15

6:15 am-6:32 pm

2 stops19h 17m

$770

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 1/6

1:28 pm-9:15 pm

2 stops24h 47m

Naples

Thu 1/15

12:15 pm-5:37 pm

2 stops36h 22m

$770

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 1/6

1:28 pm-9:15 pm

2 stops24h 47m

Naples

Mon 1/12

12:15 pm-10:07 pm

2 stops40h 52m

$778

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 1/8

6:14 pm-9:15 pm

2 stops20h 01m

Naples

Thu 1/15

6:15 am-10:07 pm

2 stops22h 52m

$815

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 4/5

12:47 pm-11:30 am

2 stops15h 43m

Naples

Tue 4/14

10:15 am-8:38 am

2 stops29h 23m

$849

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/29

5:59 pm-6:15 pm

2 stops17h 16m

Naples

Thu 5/14

10:15 am-9:45 pm

2 stops18h 30m

$849

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 4/4

6:35 pm-10:05 pm

2 stops44h 30m

Naples

Tue 4/14

10:15 am-8:38 am

2 stops29h 23m

$854

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/15

5:59 pm-6:15 pm

2 stops17h 16m

Naples

Wed 4/22

6:10 am-9:45 pm

2 stops22h 35m

$856

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 3/11

10:49 am-11:10 am

2 stops18h 21m

Naples

Fri 3/20

6:15 am-10:29 pm

2 stops22h 14m

$868

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 11 results
1
2

Compare providers for flights from Midway to Naples

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 Midway to Naples in December.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*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 Chicago Midway Airport-Naples flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Naples flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Naples flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Naples 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 Chicago Midway Airport-Naples 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 Midway to Naples

Have a flexible travel schedule? Discover the best time to fly to Naples from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Naples. 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 into for flights to Naples from Chicago Midway?

    Naples (NAP) is the airport you will fly into if you book a flight from Chicago Midway to Naples. You should not have trouble finding flights to Naples from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Naples airport from Chicago Midway. It is only a 2.9 mi journey from Naples (NAP) to Naples’s city center.

  • How long is the flight from Chicago Midway Airport to Naples?

    There are many flights that can get you from Chicago Midway Airport to Naples in 17h 16m. Fly via Delta or KLM to get the fastest option. There are 4931 mi between Chicago Midway Airport and Naples. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Naples 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 Naples?

Book flights to Naples if you plan to visit one of these locations
Praiano
Ravello
Conca Dei Marini
Maiori
Sant'Agnello
Vico Equense

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