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$396+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$1,130
(KLM)

One-way from

$396
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$894
Provider with most accurate pricing for Chicago Midway-Naples flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Naples flights.
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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. 2% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($51 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 9/301:00 pmMDW - NAP
2 stops15h 35mDelta
Tue 10/76:35 amNAP - MDW
2 stops22h 09mDelta
Deal found 4/28$917
This KLM deal was found by Cheapflights users on 4/28. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:00 amMDW - NAP
1 stop18h 00mKLM
Tue 10/79:00 amNAP - MDW
1 stop15h 58mKLM
Deal found 4/28$1,038
This Air France deal was found by Cheapflights users on 4/28. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/121:09 pmMDW - NAP
2 stops15h 26mAir France
Thu 6/199:00 amNAP - MDW
1 stop16h 02mAir France
Deal found 4/28$1,227
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/149:15 amMDW - NAP
3 stops29h 45mMultiple Airlines
Sun 9/2110:20 amNAP - MDW
3 stops37h 04mMultiple Airlines
Deal found 4/28$1,260

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 April 29, 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

1:00 pm-11:35 am

2 stops15h 35m

Naples

Tue 10/7

6:35 am-9:44 pm

2 stops22h 09m

$917

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 9/27

6:00 am-7:00 am

1 stop18h 00m

Naples

Tue 10/7

9:00 am-5:58 pm

1 stop15h 58m

$1,038

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 6/12

1:09 pm-11:35 am

2 stops15h 26m

Naples

Thu 6/19

9:00 am-6:02 pm

1 stop16h 02m

$1,227

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 9/14

9:15 am-10:00 pm

3 stops29h 45m

Naples

Sun 9/21

10:20 am-4:24 pm

3 stops37h 04m

$1,260

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 5/30

9:40 am-5:50 pm

3 stops49h 10m

$396

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 6/18

6:00 am-8:10 am

2 stops19h 10m

$838

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 6/21

4:26 pm-8:10 am

2 stops32h 44m

$853

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Naples flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Naples

Rainfall in Naples by month

Plan your trip to Naples by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Naples ranges from 0.9 - 6.4 inches per month. November is typically the wettest month, when rainfall can reach 6.4 in. July is typically the driest time to visit Naples when rainfall is around 0.9 in.

Temperature in Naples by month

Plan your trip to Naples by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Naples, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).

Reviews of airlines servicing Naples

Get insights into the airlines that provide service to Naples. 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 Naples. Reviews last updated April 29, 2025.
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air France
7.4
Good
1,444 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Naples one-way?

    For one-way options, check prices for KLM. According to our data, you can fly for as low as $834. Users have also found prices from $838 and $999 on Delta and Air France, respectively.

  • 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 $1,238). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Ravello
Caserta
Conca Dei Marini
Praiano
Sant'Agnello
Vico Equense
Procida

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