HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Midway (MDW) to Naples (NAP) from $357

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 7/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — NAP
Jun 14 — Jun 211
From?
To?
Fri 6/14
Fri 6/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

How far in advance should I book a flight from Chicago Midway Airport to Naples?

Find a great deal and save up to 8% by booking at least 36 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago Midway Airport to Naples within the next two weeks, with the cheapest ticket starting at $662.

What is the cheapest month to fly from Chicago Midway Airport to Naples?

Flights from Chicago Midway Airport to Naples lean towards being more expensive in June. Prices are generally better when you fly from Chicago Midway Airport to Naples in February, with the cheapest ticket starting at $474.

What is the cheapest time of day to fly from MDW to NAP?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Naples as you normally would.

Cheap Midway to Naples flights in June & July 2024

Find cheap flight options from Midway to Naples specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Prices were last updated on June 9, 2024.
These are some of the best deals we've found on flights to Naples in 2024 at this time. Check back soon for alternative fares.
Fri 7/126:00 amMDW - NAP
2 stops18h 30mDelta
Fri 7/266:15 amNAP - MDW
2 stops19h 24mDelta
Deal found 6/8$1,018
Fri 7/56:00 amMDW - NAP
2 stops18h 30mDelta
Wed 7/106:35 amNAP - MDW
2 stops17h 28mDelta
Deal found 6/9$1,067
Thu 7/410:41 amMDW - NAP
2 stops17h 54mAir France
Mon 7/85:15 pmNAP - MDW
2 stops32h 24mAir France
Deal found 6/9$1,087
Sat 7/66:00 amMDW - NAP
2 stops18h 30mDelta
Sat 7/136:15 amNAP - MDW
2 stops19h 24mDelta
Deal found 6/8$1,088
Sun 7/75:45 pmMDW - NAP
2 stops21h 10mDelta
Sun 7/146:15 amNAP - MDW
2 stops19h 24mDelta
Deal found 6/7$1,119
Sun 6/91:24 pmMDW - NAP
2 stops17h 56mDelta
Thu 6/206:15 amNAP - MDW
2 stops19h 21mDelta
Deal found 6/8$1,128
Fri 7/126:00 amMDW - NAP
2 stops18h 30mDelta
Mon 7/226:15 amNAP - MDW
2 stops17h 48mDelta
Deal found 6/8$1,135
Sun 7/71:24 pmMDW - NAP
2 stops15h 11mAir France
Fri 7/196:15 amNAP - MDW
2 stops19h 24mAir France
Deal found 6/8$1,164
Sun 7/76:00 amMDW - NAP
2 stops18h 30mDelta
Sun 7/146:15 amNAP - MDW
2 stops17h 48mDelta
Deal found 6/9$1,176

Midway to Naples 2024 flight deals

Discover exclusive flight deals for travel between Midway and Naples in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
These are some of the best deals we've found on flights to Naples in 2024 at this time. Check back soon for alternative fares.
Thu 9/125:45 pmMDW - NAP
2 stops17h 30mDelta
Thu 9/266:15 amNAP - MDW
2 stops19h 09mDelta
Deal found 6/8$959
Sat 9/75:45 pmMDW - NAP
2 stops17h 30mDelta
Sat 9/146:35 amNAP - MDW
2 stops17h 29mDelta
Deal found 6/9$992
Fri 7/126:00 amMDW - NAP
2 stops18h 30mDelta
Fri 7/266:15 amNAP - MDW
2 stops19h 24mDelta
Deal found 6/8$1,018
Thu 9/191:08 pmMDW - NAP
2 stops15h 27mDelta
Mon 9/306:15 amNAP - MDW
2 stops19h 09mDelta
Deal found 6/8$1,019
Fri 10/111:10 pmMDW - NAP
2 stops15h 50mDelta
Sat 10/196:15 amNAP - MDW
2 stops18h 01mDelta
Deal found 6/8$1,028
Thu 9/191:08 pmMDW - NAP
2 stops15h 27mDelta
Sat 10/56:15 amNAP - MDW
2 stops19h 09mDelta
Deal found 6/7$1,065
Fri 7/56:00 amMDW - NAP
2 stops18h 30mDelta
Wed 7/106:35 amNAP - MDW
2 stops17h 28mDelta
Deal found 6/9$1,067
Thu 7/410:41 amMDW - NAP
2 stops17h 54mAir France
Mon 7/85:15 pmNAP - MDW
2 stops32h 24mAir France
Deal found 6/9$1,087
Sat 7/66:00 amMDW - NAP
2 stops18h 30mDelta
Sat 7/136:15 amNAP - MDW
2 stops19h 24mDelta
Deal found 6/8$1,088

Midway to Naples flights leaving soon

Find last-minute flight options from Midway to Naples for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
Have a look at some of the flights available from Chicago to Naples departing last-minute. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Fri 6/141:24 pmMDW - NAP
2 stops15h 36mAir France
Sun 7/76:15 amNAP - MDW
2 stops19h 22mAir France
Deal found 6/8$1,794
Fri 6/141:24 pmMDW - NAP
2 stops15h 36mDelta
Sun 7/76:15 amNAP - MDW
2 stops19h 22mDelta
Deal found 6/9$1,890

One-way flights to Naples from Midway

Search for one-way flight options from Midway to Naples. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
Users traveling one-way from Chicago to Naples can select one of these great deals. Users can also find round-trip Chicago to Naples flights by using the search form above.
Sun 7/79:04 pmMDW - NAP
2 stops41h 01mMultiple Airlines
Deal found 6/9$357
Sun 7/79:04 pmMDW - NAP
3 stops52h 11mMultiple Airlines
Deal found 6/9$368
Fri 6/285:15 pmMDW - NAP
3 stops46h 40mMultiple Airlines
Deal found 6/9$555
Fri 6/289:34 amMDW - NAP
2 stops19h 01mDelta
Deal found 6/9$962

Find flights from Midway to Naples within your budget

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 3,020,828 searches. Data last updated June 9, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$948 - $1,463

Route

Depart

Return

Price

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 6/24

2 stops18h 30m

Naples

Wed 7/3

2 stops19h 22m

$948

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 9/7

2 stops17h 30m

Naples

Sat 9/14

2 stops17h 29m

$992

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 7/12

2 stops18h 30m

Naples

Fri 7/26

2 stops19h 24m

$1,018

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 7/7

2 stops19h 01m

Naples

Fri 7/19

2 stops19h 24m

$1,053

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 7/5

2 stops18h 30m

Naples

Wed 7/10

2 stops17h 28m

$1,067

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 7/4

2 stops17h 54m

Naples

Mon 7/8

2 stops32h 24m

$1,087

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 9/6

2 stops19h 02m

Naples

Sun 9/22

2 stops18h 47m

$1,138

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 7/7

3 stops31h 00m

Naples

Sun 7/14

2 stops33h 27m

$1,283

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 7/7

3 stops20h 35m

Naples

Sun 7/14

3 stops18h 27m

$1,463

Flights are sorted by cheapest first

Deals found on 6/9

No data available for this route at this time. Please check back soon.

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.

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 9, 2024.
Read through reviews of airlines operating flights from Chicago to Naples, such as Delta 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
10,295 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,295 reviews
Delta
8.0
Very good
10,295 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Air France
7.5
Good
1,711 reviews
Delta
8.0
Very good
10,295 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

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.

  • Can I find flights from Chicago Midway Airport to Naples for under $1,000 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Naples for under $1,000. The cheapest flight booked recently is on Delta for just $948, but on average you can expect to pay $1,310.

  • Are there last-minute flights available from Chicago Midway Airport to Naples for under $1,800?

    There are currently 2+ open flights from Chicago Midway Airport to Naples within the next 7 days for less than $1,800.

  • What does MDW to NAP mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago Midway Airport to Naples Airport flight would often be abbreviated as a MDW to NAP flight.

  • Can I find deals for flights from Midway to Naples that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Naples flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Naples with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Naples flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to Naples that allow pets onboard?

    Many airlines flying from Midway to Naples offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Naples?

    Yes, you can often find last-minute deals on Midway to Naples flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Naples flight deals updated?

    The Chicago Midway Airport to Naples flight deals you see on this page were last updated on 6/9.

  • 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 $663). Flying from Chicago Midway Airport to Naples in June is currently the most expensive (average of $1,398). 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

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
Orlando to Las Vegas flights
Charlotte to Miami flights
Tampa to New York flights
Fresno to Las Vegas flights
New York to Paris flights
Portland to Phoenix flights
Miami to Denver flights
New York to Guyana flights
Las Vegas to Miami flights
San Francisco to Dubai flights
Chicago Midway Airport to Nassau flights

Search flights from Midway to Naples by cabin class

Find flights from Midway to Naples, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Gaziantep
Flights to Miyakojima Hirara
Flights to Figari-Sud Corse
Flights to Mason City
Flights to Komatsu
Flights to Sendai
Flights to Rhinelander Oneida County
Flights to Constanţa Mihail Kogalniceanu
Flights to Brainerd Crow Wing County
Flights to Reus
Flights to Virac
Flights to Neiva La Marguita
Flights to Pellston Emmet County
Flights to Urumqi
Flights to Bastia Poretta
Flights to Samos
Flights to Hyannis Barnstable
Flights to Provincetown
Flights to Alghero-Fertilia
Flights to Laayoune Hassan I
Flights to Devils Lake
Flights to Vava'u Lupepau'U
Flights to Hakodate
Flights to Edremit/Korfez
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.
View all available airlines