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$306+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This KAYAK deal was found by Cheapflights users on 2/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:35 am
MDW
-
NAP
1 stop13h 30m
Scandinavian Airlines
Tue 8/256:05 am
NAP
-
MDW
2 stops17h 22m
Scandinavian Airlines
Deal found 2/4$557
This Delta deal was found by Cheapflights users on 2/3. 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 3/31:49 pm
MDW
-
NAP
2 stops19h 01m
Delta
Tue 3/106:15 am
NAP
-
MDW
2 stops18h 25m
Delta
Deal found 2/3$559
This Delta deal was found by Cheapflights users on 2/1. 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.
Mon 2/161:49 pm
MDW
-
NAP
2 stops19h 01m
Delta
Wed 3/46:15 am
NAP
-
MDW
2 stops19h 25m
Delta
Deal found 2/1$560
This KLM deal was found by Cheapflights users on 2/3. 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 3/101:10 pm
MDW
-
NAP
2 stops14h 25m
KLM
Tue 3/176:35 am
NAP
-
MDW
2 stops17h 19m
KLM
Deal found 2/3$561
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:29 pm
MDW
-
NAP
2 stops13h 16m
KLM
Thu 3/126:35 am
NAP
-
MDW
2 stops17h 19m
KLM
Deal found 2/2$661
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:31 am
MDW
-
NAP
2 stops18h 59m
Delta
Tue 5/56:05 am
NAP
-
MDW
2 stops19h 31m
Delta
Deal found 2/2$710
This KLM deal was found by Cheapflights users on 2/1. 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 2/269:34 am
MDW
-
NAP
2 stops17h 11m
KLM
Wed 3/46:15 am
NAP
-
MDW
2 stops18h 30m
KLM
Deal found 2/1$721
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:30 am
MDW
-
NAP
2 stops14h 35m
Delta
Tue 8/2510:15 am
NAP
-
MDW
2 stops18h 31m
Delta
Deal found 2/4$724
This Delta deal was found by Cheapflights users on 2/1. 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.
Mon 4/136:00 am
MDW
-
NAP
2 stops19h 10m
Delta
Mon 4/2010:15 am
NAP
-
MDW
2 stops19h 13m
Delta
Deal found 2/1$747
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:59 pm
MDW
-
NAP
2 stops17h 16m
Delta
Sat 8/226:05 am
NAP
-
MDW
2 stops19h 26m
Delta
Deal found 2/2$786
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/281:28 pm
MDW
-
NAP
2 stops14h 42m
Multiple Airlines
Sat 3/76:15 am
NAP
-
MDW
2 stops16h 59m
Multiple Airlines
Deal found 2/2$817
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/201:23 pm
MDW
-
NAP
2 stops18h 52m
Delta
Mon 5/46:05 am
NAP
-
MDW
2 stops23h 23m
Delta
Deal found 2/2$819

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$559
(Delta)

One-way from

$306
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$540
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 ($234 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 5, 2026.
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

Tue 3/10

2:05 pm-3:50 pm

2 stops19h 45m

Naples

Tue 3/17

6:15 am-5:54 pm

2 stops17h 39m

$559

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 2/16

1:49 pm-3:50 pm

2 stops19h 01m

Naples

Wed 3/4

6:15 am-6:40 pm

2 stops19h 25m

$560

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 3/5

1:29 pm-9:45 am

2 stops13h 16m

Naples

Thu 3/12

6:35 am-5:54 pm

2 stops17h 19m

$661

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 4/26

9:31 am-11:30 am

2 stops18h 59m

Naples

Tue 5/5

6:05 am-6:36 pm

2 stops19h 31m

$710

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 2/28

1:28 pm-11:10 am

2 stops14h 42m

Naples

Sat 3/7

6:15 am-4:14 pm

2 stops16h 59m

$817

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 4/20

1:23 pm-3:15 pm

2 stops18h 52m

Naples

Mon 5/4

6:05 am-10:28 pm

2 stops23h 23m

$819

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 4/14

6:00 am-8:10 am

2 stops19h 10m

Naples

Sun 4/19

6:05 am-5:58 pm

2 stops18h 53m

$835

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 3/30

9:30 am-11:30 am

2 stops19h 00m

Naples

Tue 4/14

10:15 am-10:28 pm

2 stops19h 13m

$851

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 5/11

1:22 pm-3:15 pm

2 stops18h 53m

Naples

Wed 5/20

6:05 am-5:56 pm

2 stops18h 51m

$860

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 4/9

9:30 am-11:30 am

2 stops19h 00m

Naples

Sun 4/19

6:05 am-5:58 pm

2 stops18h 53m

$895

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 19 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 February.
ProviderPrice AccuracyTrust Score*
OvagoPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Naples flight deals on Cheapflights vs. FlightHub >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 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 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 13h 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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Alternative routes for Midway to Naples

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