HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Naples

$600+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Naples with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$605
(Air France)

One-way from

$600
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$824
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. 23% potential increase in price ($264 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 28, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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 11/249:34 amMDW - NAP
2 stops23h 16mDelta
Mon 12/86:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 10/28$655
This Delta deal was found by Cheapflights users on 10/28. 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 12/101:14 pmMDW - NAP
2 stops14h 56mDelta
Wed 12/176:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 10/28$661
This Delta deal was found by Cheapflights users on 10/27. 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 11/101:15 pmMDW - NAP
2 stops19h 35mDelta
Mon 11/246:15 amNAP - MDW
2 stops19h 03mDelta
Deal found 10/27$681
This Trip.com deal was found by Cheapflights users on 10/27. 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 11/2310:47 amMDW - NAP
2 stops22h 18mMultiple Airlines
Tue 12/96:35 amNAP - MDW
2 stops18h 25mMultiple Airlines
Deal found 10/27$737
This Delta deal was found by Cheapflights users on 10/27. 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 11/81:06 pmMDW - NAP
2 stops19h 44mDelta
Sat 11/1511:50 amNAP - MDW
2 stops18h 50mDelta
Deal found 10/27$801
This Delta deal was found by Cheapflights users on 10/27. 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 12/111:14 pmMDW - NAP
2 stops19h 36mDelta
Thu 12/1811:50 amNAP - MDW
2 stops18h 57mDelta
Deal found 10/27$925
This Delta deal was found by Cheapflights users on 10/27. 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 11/2510:47 amMDW - NAP
2 stops22h 03mDelta
Tue 12/26:15 amNAP - MDW
2 stops18h 45mDelta
Deal found 10/27$1,092
This Delta deal was found by Cheapflights users on 10/27. 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 10/281:48 pmMDW - NAP
2 stops20h 02mDelta
Tue 11/46:15 amNAP - MDW
2 stops22h 59mDelta
Deal found 10/27$1,336
This Delta deal was found by Cheapflights users on 10/27. 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 11/2612:47 pmMDW - NAP
2 stops15h 23mDelta
Sun 11/3011:50 amNAP - MDW
2 stops18h 50mDelta
Deal found 10/27$1,624
This Delta deal was found by Cheapflights users on 10/26. 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 12/249:29 amMDW - NAP
2 stops18h 41mDelta
Fri 1/26:15 amNAP - MDW
2 stops18h 11mDelta
Deal found 10/26$2,204
This Delta deal was found by Cheapflights users on 10/27. 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 12/286:08 pmMDW - NAP
2 stops20h 07mDelta
Fri 1/26:15 amNAP - MDW
2 stops18h 11mDelta
Deal found 10/27$2,360

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 October 28, 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 1/14

1:28 pm-11:30 am

2 stops15h 02m

Naples

Wed 1/21

6:15 am-5:32 pm

2 stops18h 17m

$606

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 11/24

9:34 am-3:50 pm

2 stops23h 16m

Naples

Mon 12/8

6:15 am-6:00 pm

2 stops18h 45m

$655

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 12/10

1:14 pm-11:10 am

2 stops14h 56m

Naples

Wed 12/17

6:15 am-6:00 pm

2 stops18h 45m

$661

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 11/9

6:00 am-11:30 am

2 stops22h 30m

Naples

Mon 11/24

6:15 am-6:18 pm

2 stops19h 03m

$681

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 11/10

1:15 pm-3:50 pm

2 stops19h 35m

Naples

Mon 11/24

6:15 am-6:18 pm

2 stops19h 03m

$681

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 2/23

9:30 am-3:50 pm

2 stops23h 20m

Naples

Sun 3/1

6:15 am-6:34 pm

2 stops19h 19m

$710

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 11/23

10:47 am-4:05 pm

2 stops22h 18m

Naples

Tue 12/9

6:35 am-6:00 pm

2 stops18h 25m

$737

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 4/2

1:00 pm-10:05 pm

2 stops26h 05m

Naples

Mon 4/6

12:30 pm-9:46 pm

2 stops40h 16m

$775

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 11/8

1:06 pm-3:50 pm

2 stops19h 44m

Naples

Sat 11/15

11:50 am-11:40 pm

2 stops18h 50m

$801

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 12/15

8:42 pm-1:40 pm

3 stops33h 58m

$600

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 15h 02m. Fly via KLM or Delta 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Naples

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

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.