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$293+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NAP
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$788
(Delta)

One-way from

$293
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$1,221
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. 3% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This KLM deal was found by Cheapflights users on 6/10. 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
Mon 9/296:10 amNAP - MDW
2 stops17h 13mKLM
Deal found 6/10$781
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 8/166:04 amMDW - NAP
1 stop17h 56mDelta
Sat 8/236:10 amNAP - MDW
2 stops18h 27mDelta
Deal found 6/11$788
This Air France deal was found by Cheapflights users on 6/12. 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.
Sat 11/15:59 pmMDW - NAP
2 stops15h 51mAir France
Tue 11/116:05 amNAP - MDW
2 stops19h 31mAir France
Deal found 6/12$1,039
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Wed 7/169:40 amMDW - NAP
3 stops25h 15mMultiple Airlines
Wed 7/2311:35 amNAP - MDW
2 stops35h 49mMultiple Airlines
Deal found 6/11$1,172

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 June 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

Sat 8/16

6:04 am-7:00 am

1 stop17h 56m

Naples

Sat 8/23

6:10 am-5:37 pm

2 stops18h 27m

$788

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 8/16

10:11 am-7:00 am

1 stop13h 49m

Naples

Sat 8/23

9:00 am-9:12 pm

1 stop19h 12m

$815

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/26

1:08 pm-11:35 am

2 stops15h 27m

Naples

Sun 8/31

9:00 am-9:12 pm

1 stop19h 12m

$1,086

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 7/16

9:40 am-5:55 pm

3 stops25h 15m

Naples

Wed 7/23

11:35 am-4:24 pm

2 stops35h 49m

$1,172

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 6/22

9:40 am-12:20 pm

2 stops43h 40m

$324

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 7/14

6:00 am-7:05 am

1 stop18h 05m

$526

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 7/14

6:00 am-8:10 am

2 stops19h 10m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 2025.
Read through reviews of airlines operating flights from Chicago to Naples, such as Delta, KLM and Air France. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,463 reviews
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $446. Users have also found prices from $548 and $1,286 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 $1,217). 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
Conca Dei Marini
Caserta
Ravello
Sant'Agnello
Vico Equense
Praiano
Procida

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O'Hare Intl to Naples flights

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