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$311+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$589
(Delta)

One-way from

$311
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$884
From Chicago Midway to Naples
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One-way flight from Chicago Midway to Naples
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Highest demand for flights based on searches. 1% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($48 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 9/306:30 pmMDW - NAP
2 stops16h 45mDelta
Tue 10/79:00 amNAP - MDW
1 stop20h 14mDelta
Deal found 9/10$589
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 9/226:00 amMDW - NAP
1 stop18h 00mDelta
Thu 10/26:10 amNAP - MDW
2 stops19h 25mDelta
Deal found 9/10$597
This Trip.com deal was found by Cheapflights users on 9/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:35 amMDW - NAP
1 stop13h 25mKLM
Wed 11/54:45 pmNAP - MDW
2 stops30h 29mKLM
Deal found 9/10$605
This Trip.com deal was found by Cheapflights users on 9/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:30 pmMDW - NAP
1 stop29h 30mMultiple Airlines
Tue 10/146:10 amNAP - MDW
2 stops23h 04mMultiple Airlines
Deal found 9/9$626
This Air France deal was found by Cheapflights users on 9/11. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:00 amMDW - NAP
1 stop18h 00mMultiple Airlines
Tue 10/79:00 amNAP - MDW
1 stop20h 14mMultiple Airlines
Deal found 9/11$630
This KLM deal was found by Cheapflights users on 9/10. 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.
Mon 9/226:00 amMDW - NAP
1 stop18h 00mKLM
Thu 10/29:00 amNAP - MDW
1 stop19h 36mKLM
Deal found 9/10$662
This Delta deal was found by Cheapflights users on 9/11. 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.
Sun 9/286:00 amMDW - NAP
2 stops19h 10mDelta
Tue 10/79:00 amNAP - MDW
1 stop20h 14mDelta
Deal found 9/11$666
This KLM deal was found by Cheapflights users on 9/10. 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.
Sun 9/216:30 pmMDW - NAP
1 stop29h 30mKLM
Thu 10/29:00 amNAP - MDW
1 stop15h 35mKLM
Deal found 9/10$667
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 10/206:00 amMDW - NAP
1 stop18h 00mDelta
Sat 11/1511:50 amNAP - MDW
2 stops18h 42mDelta
Deal found 9/9$681

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 September 11, 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

Tue 9/30

6:30 pm-6:15 pm

2 stops16h 45m

Naples

Tue 10/7

9:00 am-10:14 pm

1 stop20h 14m

$589

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 10/20

10:35 am-7:00 am

1 stop13h 25m

Naples

Wed 11/5

4:45 pm-4:14 pm

2 stops30h 29m

$605

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 11/5

10:40 am-11:10 am

2 stops17h 30m

Naples

Tue 11/18

6:15 am-6:08 pm

2 stops18h 53m

$662

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 9/21

6:30 pm-7:00 am

1 stop29h 30m

Naples

Thu 10/2

9:00 am-5:35 pm

1 stop15h 35m

$667

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 10/20

6:00 am-7:00 am

1 stop18h 00m

Naples

Sat 11/15

11:50 am-11:32 pm

2 stops18h 42m

$681

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/21

6:00 am-8:10 am

2 stops19h 10m

Naples

Sun 11/16

11:50 am-11:32 pm

2 stops18h 42m

$686

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/14

6:00 am-8:10 am

2 stops19h 10m

Naples

Tue 10/21

9:00 am-10:14 pm

1 stop20h 14m

$700

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 9/21

6:15 pm-6:15 pm

2 stops17h 00m

Naples

Thu 10/2

6:10 am-6:35 pm

2 stops19h 25m

$708

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 10/8

6:00 am-7:00 am

1 stop18h 00m

Naples

Mon 10/13

6:10 am-6:25 pm

2 stops19h 15m

$748

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/14

8:05 am-6:50 pm

3 stops51h 45m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 20 results
1
2

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 25m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Naples?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Naples (average of $703). Flying from Chicago Midway Airport to Naples in June is currently the most expensive (average of $1,202). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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