Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to Naples from $430

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Naples departing on 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Naples

Cheap round-trip flights

Enter your travel dates to find the best prices.
KLM Logo
1:10 pm - 9:35 am
MDW
-
NAP
14h 25m
2 stops
KLM Logo
6:35 am - 5:54 pm
NAP
-
MDW
17h 19m
2 stops
$561KLM
Tue, Mar 10 - Tue, Mar 17
Delta Logo
1:49 pm - 3:50 pm
MDW
-
NAP
19h 01m
2 stops
Delta Logo
6:15 am - 6:40 pm
NAP
-
MDW
18h 25m
2 stops
$609Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
6:34 pm - 6:15 pm
MDW
-
NAP
16h 41m
2 stops
Delta Logo
6:05 am - 4:25 pm
NAP
-
MDW
17h 20m
2 stops
$709Delta
Sun, Apr 12 - Thu, Apr 23
Delta Logo
9:30 am - 11:30 am
MDW
-
NAP
19h 00m
2 stops
Delta Logo
10:15 am - 10:28 pm
NAP
-
MDW
19h 13m
2 stops
$809Delta
Sat, Apr 4 - Fri, Apr 17
Delta Logo
10:45 am - 11:30 am
MDW
-
NAP
17h 45m
2 stops
Delta Logo
6:05 am - 6:40 pm
NAP
-
MDW
19h 35m
2 stops
$859Delta
Wed, Apr 1 - Wed, Apr 8
Delta Logo
1:22 pm - 3:15 pm
MDW
-
NAP
18h 53m
2 stops
Delta Logo
6:05 am - 5:56 pm
NAP
-
MDW
18h 51m
2 stops
$914Delta
Mon, May 11 - Fri, May 22
Delta Logo
1:22 pm - 3:15 pm
MDW
-
NAP
18h 53m
2 stops
Delta Logo
6:05 am - 5:56 pm
NAP
-
MDW
18h 51m
2 stops
$917Delta
Mon, May 11 - Wed, May 20
Delta Logo
10:35 am - 7:05 am
MDW
-
NAP
13h 30m
1 stop
Delta Logo
6:05 am - 6:31 pm
NAP
-
MDW
19h 26m
2 stops
$955Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
9:30 am - 7:05 am
MDW
-
NAP
14h 35m
2 stops
Delta Logo
6:05 am - 6:31 pm
NAP
-
MDW
19h 26m
2 stops
$959Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
10:45 am - 11:30 am
MDW
-
NAP
17h 45m
2 stops
Delta Logo
6:05 am - 6:40 pm
NAP
-
MDW
19h 35m
2 stops
$962Delta
Wed, Apr 1 - Wed, Apr 8

Delta flights from Chicago Midway Airport to Naples

Our best Delta deals on Chicago Midway Airport to Naples flight tickets
Delta
Mar 2
MDW1:49 pmChicago Midway
19h 01m
2 stops
NAP3:50 pmNaples
Mar 9
NAP6:15 amNaples
18h 25m
2 stops
MDW6:40 pmChicago Midway
$609
Delta
Apr 12
MDW6:34 pmChicago Midway
16h 41m
2 stops
NAP6:15 pmNaples
Apr 23
NAP6:05 amNaples
17h 20m
2 stops
MDW4:25 pmChicago Midway
$709
Delta
Apr 4
MDW9:30 amChicago Midway
19h 00m
2 stops
NAP11:30 amNaples
Apr 17
NAP10:15 amNaples
19h 13m
2 stops
MDW10:28 pmChicago Midway
$809

KLM flights from Chicago Midway Airport to Naples

Our best KLM deals on Chicago Midway Airport to Naples flight tickets
KLM
Mar 10
MDW1:10 pmChicago Midway
14h 25m
2 stops
NAP9:35 amNaples
Mar 17
NAP6:35 amNaples
17h 19m
2 stops
MDW5:54 pmChicago Midway
$561
KLM
Aug 8
MDW10:35 amChicago Midway
13h 30m
1 stop
NAP7:05 amNaples
Aug 17
NAP9:15 amNaples
19h 31m
1 stop
MDW9:46 pmChicago Midway
$973

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Naples that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 3/10

1:10 pm-9:35 am

2 stops14h 25m

Naples

Tue 3/17

6:35 am-5:54 pm

2 stops17h 19m

$561

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 3/2

1:49 pm-3:50 pm

2 stops19h 01m

Naples

Mon 3/9

6:15 am-6:40 pm

2 stops18h 25m

$609

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 4/12

6:34 pm-6:15 pm

2 stops16h 41m

Naples

Thu 4/23

6:05 am-4:25 pm

2 stops17h 20m

$709

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 4/4

9:30 am-11:30 am

2 stops19h 00m

Naples

Fri 4/17

10:15 am-10:28 pm

2 stops19h 13m

$809

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/1

10:45 am-11:30 am

2 stops17h 45m

Naples

Wed 4/8

6:05 am-6:40 pm

2 stops19h 35m

$859

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 5/11

1:22 pm-3:15 pm

2 stops18h 53m

Naples

Fri 5/22

6:05 am-5:56 pm

2 stops18h 51m

$914

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 5/11

1:22 pm-3:15 pm

2 stops18h 53m

Naples

Wed 5/20

6:05 am-5:56 pm

2 stops18h 51m

$917

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 8/8

10:35 am-7:05 am

1 stop13h 30m

Naples

Sat 8/15

6:05 am-6:31 pm

2 stops19h 26m

$955

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 8/8

9:30 am-7:05 am

2 stops14h 35m

Naples

Sat 8/15

6:05 am-6:31 pm

2 stops19h 26m

$959

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 4/1

10:45 am-11:30 am

2 stops17h 45m

Naples

Wed 4/8

6:05 am-6:40 pm

2 stops19h 35m

$962

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Naples from

How to get the cheapest flight ticket from Chicago Midway Airport to Naples

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Naples?

Our data shows that Tuesday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $887. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Naples for around $1,183.

What is the cheapest time of day to depart on your flight to Naples?

Our data shows that the cheapest Chicago Midway Airport to Naples flights are usually those with departure times in the evening. Our users have found flights to Naples in the evening for as low as $1,025. In the afternoon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,131 per ticket.

When to book flights from Chicago Midway Airport to Naples

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Naples according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Naples (MDW to NAP) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Naples

Fastest flight time

13h 19m

Direct flights

None
The fastest flight from Chicago Midway Airport to Naples takes 13h 19m
There are no direct flights from Chicago Midway Airport to Naples. There are no popular flight routes from Chicago Midway Airport to Naples.
Search flight deals

  • How far is Chicago Midway to Naples by plane?

    The distance between Chicago Midway and Naples is about 4931.9 mi. In terms of flight time, this usually takes a little over 13h 19m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Naples Airport?

    Prices for flights from Chicago Midway Airport to Naples Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Naples Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Naples Airport.

  • What documentation or ID do you need to fly to Naples Airport?

    The travel and health documents required for your trip to Naples Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Naples Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Naples?

Book flights to Naples if you plan to visit one of these locations
Amalfi
Positano
Capri
Sorrento
Praiano
Ravello
Ischia
Maiori
Sant'Agnello
Pompei
Procida
Atrani
Anacapri
Furore
Minori
Ercolano
Vietri sul Mare
Nola
Vico Equense
Conca Dei Marini

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Naples?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Naples for you.

Can I find flights from Chicago to Naples with flexible booking policies on momondo?

Yes. All flights to Naples from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Naples?

Once you have performed a search for Chicago to Naples flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Naples right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Naples from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Naples trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 3/13
Fri 3/20
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Italy

Airports servicing Campania

Salerno Costa d'Amalfi Airport