HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Midway (MDW) to Naples (NAP) from $282

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 5/19. 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
May 4 — May 111
From?
To?
Sat 5/4
Sat 5/11
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 90% by booking at least 33 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 $1,050.

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 July. Prices are generally better when you fly from Chicago Midway Airport to Naples in January, with the cheapest ticket starting at $591.

When is the cheapest time to fly from Chicago Midway Airport to Naples (MDW - 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 Delta flights from Midway to Naples

Explore cheap flight options specifically provided by Delta for the route between Midway and Naples. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 29, 2024.
Check out some of the cheapest Delta flights we've come across from Chicago to Naples. Make sure to double check the flight details before booking.
Sat 7/206:00 amMDW - NAP
2 stops18h 30mDelta
Sat 7/276:15 amNAP - MDW
2 stops17h 50mDelta
Deal found 4/28$981
Mon 5/1312:42 pmMDW - NAP
2 stops18h 38mDelta
Sun 5/196:25 amNAP - MDW
2 stops22h 36mDelta
Deal found 4/28$1,004
Sun 6/96:00 amMDW - NAP
2 stops18h 30mDelta
Thu 6/206:35 amNAP - MDW
2 stops17h 29mDelta
Deal found 4/28$1,031
Tue 6/46:00 amMDW - NAP
2 stops18h 30mDelta
Tue 6/116:15 amNAP - MDW
2 stops19h 21mDelta
Deal found 4/29$1,040
Thu 6/66:00 amMDW - NAP
2 stops18h 30mDelta
Thu 6/139:30 amNAP - MDW
2 stops19h 16mDelta
Deal found 4/29$1,062
Sat 5/1811:59 amMDW - NAP
2 stops16h 36mDelta
Sun 5/266:15 amNAP - MDW
2 stops17h 40mDelta
Deal found 4/29$1,074
Wed 6/126:00 amMDW - NAP
2 stops18h 30mDelta
Thu 6/276:15 amNAP - MDW
2 stops17h 49mDelta
Deal found 4/29$1,309
Wed 6/126:00 amMDW - NAP
2 stops18h 30mDelta
Thu 6/276:15 amNAP - MDW
2 stops17h 49mDelta
Deal found 4/28$1,364
Wed 7/246:00 amMDW - NAP
2 stops18h 30mDelta
Sat 8/36:15 amNAP - MDW
2 stops19h 11mDelta
Deal found 4/28$1,379

Cheap Air France flights from Midway to Naples

Explore cheap flight options specifically provided by Air France for the route between Midway and Naples. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,948,547 searches. Data last updated April 29, 2024.
Browse through some of the cheapest Air France flights traveling from Chicago to Naples. Make sure to examine the flight information before completing your reservation.
Fri 7/122:25 pmMDW - NAP
2 stops20h 50mAir France
Mon 7/227:15 pmNAP - MDW
2 stops28h 50mAir France
Deal found 4/28$1,141
Sat 7/275:45 pmMDW - NAP
2 stops21h 10mAir France
Mon 8/57:15 pmNAP - MDW
2 stops29h 44mAir France
Deal found 4/29$1,276
Thu 5/232:15 pmMDW - NAP
2 stops24h 40mAir France
Sun 6/96:15 amNAP - MDW
2 stops18h 44mAir France
Deal found 4/28$1,557
Thu 5/162:15 pmMDW - NAP
2 stops14h 20mAir France
Sat 5/256:15 amNAP - MDW
2 stops16h 58mAir France
Deal found 4/29$1,562
Fri 6/141:24 pmMDW - NAP
2 stops25h 31mAir France
Sun 7/73:10 pmNAP - MDW
2 stops32h 55mAir France
Deal found 4/28$1,617
Fri 6/141:24 pmMDW - NAP
2 stops25h 31mAir France
Sun 7/77:15 pmNAP - MDW
2 stops30h 11mAir France
Deal found 4/29$1,679

Cheap Midway to Naples flights in April & May 2024

Find cheap flight options from Midway to Naples specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Prices were last updated on April 29, 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.
Mon 5/1312:42 pmMDW - NAP
2 stops18h 38mDelta
Sun 5/196:25 amNAP - MDW
2 stops22h 36mDelta
Deal found 4/28$1,004
Sat 5/1811:59 amMDW - NAP
2 stops16h 36mDelta
Sun 5/266:15 amNAP - MDW
2 stops17h 40mDelta
Deal found 4/29$1,074
Sun 5/58:40 amMDW - NAP
3 stops30h 15mMultiple Airlines
Sun 5/196:15 amNAP - MDW
3 stops22h 22mMultiple Airlines
Deal found 4/28$1,142
Wed 5/225:47 pmMDW - NAP
2 stops17h 28mDelta
Fri 5/316:25 amNAP - MDW
2 stops17h 41mDelta
Deal found 4/28$1,406
Thu 5/232:15 pmMDW - NAP
2 stops24h 40mAir France
Sun 6/96:15 amNAP - MDW
2 stops18h 44mAir France
Deal found 4/28$1,557
Sun 5/55:45 pmMDW - NAP
2 stops17h 30mDelta
Sun 5/196:25 amNAP - MDW
2 stops22h 36mDelta
Deal found 4/28$1,667
Sat 5/115:47 pmMDW - NAP
2 stops17h 28mDelta
Tue 5/216:25 amNAP - MDW
2 stops22h 36mDelta
Deal found 4/28$1,887
Mon 5/2012:42 pmMDW - NAP
2 stops18h 38mDelta
Sat 5/259:30 amNAP - MDW
2 stops19h 31mDelta
Deal found 4/28$1,927
Thu 5/21:25 pmMDW - NAP
2 stops15h 10mDelta
Thu 5/96:25 amNAP - MDW
2 stops22h 36mDelta
Deal found 4/29$1,967

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 2,948,547 searches. Data last updated April 29, 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.
Sun 8/181:10 pmMDW - NAP
2 stops15h 25mDelta
Tue 8/276:35 amNAP - MDW
2 stops22h 12mDelta
Deal found 4/28$755
Thu 10/312:05 pmMDW - NAP
2 stops17h 40mAir France
Sat 11/166:10 amNAP - MDW
2 stops18h 49mAir France
Deal found 4/28$821
Thu 8/156:00 amMDW - NAP
2 stops18h 30mDelta
Mon 8/266:35 amNAP - MDW
2 stops22h 12mDelta
Deal found 4/28$828
Sun 9/15:59 pmMDW - NAP
2 stops20h 56mDelta
Wed 9/116:35 amNAP - MDW
2 stops18h 24mDelta
Deal found 4/28$900
Fri 10/256:00 amMDW - NAP
2 stops18h 30mDelta
Sat 11/96:10 amNAP - MDW
2 stops18h 55mDelta
Deal found 4/28$950
Sat 9/215:00 pmMDW - NAP
2 stops18h 15mDelta
Sat 9/286:15 amNAP - MDW
2 stops18h 50mDelta
Deal found 4/28$978
Sat 7/206:00 amMDW - NAP
2 stops18h 30mDelta
Sat 7/276:15 amNAP - MDW
2 stops17h 50mDelta
Deal found 4/28$981
Sat 8/319:35 amMDW - NAP
2 stops19h 00mDelta
Mon 9/96:35 amNAP - MDW
2 stops17h 28mDelta
Deal found 4/28$985
Sun 8/113:45 pmMDW - NAP
2 stops19h 30mAir France
Sat 8/177:15 pmNAP - MDW
2 stops28h 48mAir France
Deal found 4/28$996

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 2,948,547 searches. Data last updated April 29, 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.
Sun 5/58:40 amMDW - NAP
3 stops30h 15mMultiple Airlines
Sun 5/196:15 amNAP - MDW
3 stops22h 22mMultiple Airlines
Deal found 4/28$1,142
Sun 5/55:45 pmMDW - NAP
2 stops17h 30mDelta
Sun 5/196:25 amNAP - MDW
2 stops22h 36mDelta
Deal found 4/28$1,667

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 2,948,547 searches. Data last updated April 29, 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 5/197:49 amMDW - NAP
2 stops31h 56mMultiple Airlines
Deal found 4/27$282
Mon 6/248:27 amMDW - NAP
2 stops31h 23mMultiple Airlines
Deal found 4/28$335
Sun 6/92:26 pmMDW - NAP
3 stops59h 19mMultiple Airlines
Deal found 4/28$381
Sun 6/92:26 pmMDW - NAP
2 stops49h 24mMultiple Airlines
Deal found 4/28$384
Mon 6/248:27 amMDW - NAP
3 stops29h 33mMultiple Airlines
Deal found 4/28$392
Wed 5/87:17 pmMDW - NAP
2 stops44h 28mMultiple Airlines
Deal found 4/27$455
Sun 5/197:23 pmMDW - NAP
3 stops40h 37mMultiple Airlines
Deal found 4/27$479
Thu 5/97:13 pmMDW - NAP
2 stops44h 32mMultiple Airlines
Deal found 4/27$494
Thu 5/97:00 amMDW - NAP
3 stops32h 45mMultiple Airlines
Deal found 4/27$508

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 2,948,547 searches. Data last updated April 29, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$981 - $1,328

Route

Depart

Return

Price

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 7/20

2 stops18h 30m

Naples

Sat 7/27

2 stops17h 50m

$981

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 5/13

2 stops18h 38m

Naples

Sun 5/19

2 stops22h 36m

$1,004

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 6/9

2 stops18h 30m

Naples

Thu 6/20

2 stops17h 29m

$1,031

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 6/4

2 stops18h 30m

Naples

Tue 6/11

2 stops19h 21m

$1,040

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 6/6

2 stops18h 30m

Naples

Thu 6/13

2 stops19h 16m

$1,062

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 7/12

2 stops20h 50m

Naples

Mon 7/22

2 stops28h 50m

$1,141

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 5/5

3 stops30h 15m

Naples

Sun 5/19

3 stops22h 22m

$1,142

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 7/27

2 stops21h 10m

Naples

Mon 8/5

2 stops29h 44m

$1,276

Chicago MidwayNaples

MDW - NAP

MDWNAP

Chicago Midway

Thu 5/23

3 stops31h 55m

Naples

Mon 5/27

3 stops21h 37m

$1,328

Flights are sorted by cheapest first

Deals found on 4/28

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

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, 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
8.1
Very good
10,913 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,913 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Air France
7.6
Good
1,798 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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 $981, but on average you can expect to pay $1,275.

  • Are there last-minute flights available from Chicago Midway Airport to Naples for under $1,200?

    There are currently 2+ open flights from Chicago Midway Airport to Naples within the next 7 days for less than $1,200.

  • 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 4/28.

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 Perugia Sant Egidio
Flights to Biarritz Parme
Flights to Argostoli Cephalonia
Flights to Melilla
Flights to Milas–Bodrum
Flights to Girona Costa Brava
Flights to Hakodate
Flights to Fez Sais
Flights to Constantine Ain El Bey
Flights to Zakynthos Dionsios Salomos
Flights to Bourgas
Flights to Bodø
Flights to Reggio Calabria Tito Menniti
Flights to Bastia Poretta
Flights to Skiathos
Flights to Kalamata
Flights to Batumi
Flights to Menorca/Mahon
Flights to Kristiansand Kjevik
Flights to Champaign University-Willard
Flights to Kagoshima
Flights to Ohrid
Flights to Clermont-Ferrand Aulnat
Flights to Parikia Paros

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway to Naples?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Naples from Midway today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Midway to Naples?

Millions of users choose and trust Cheapflights to book the best flight deals from Midway to Naples for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Midway to Naples with no change fees?

Yes, we can. To see specific flights from Midway to Naples with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Midway to Naples become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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