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Cheap flights from Chicago Midway Airport to Naples from $338

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 10/13. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Naples

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air France Logo
1:25 pm - 10:35 am
MDW
-
NAP
14h 10m
2 stops
Air France Logo
9:05 am - 10:36 pm
NAP
-
MDW
20h 31m
1 stop
$801Air France
Wed, Aug 19 - Wed, Aug 26
Multiple Airlines Logo
6:05 am - 7:05 am
MDW
-
NAP
18h 00m
1 stop
Multiple Airlines Logo
6:05 am - 4:15 pm
NAP
-
MDW
17h 10m
2 stops
$804Multiple Airlines
Sun, Aug 9 - Tue, Aug 25
Delta Logo
1:25 pm - 11:30 am
MDW
-
NAP
15h 05m
2 stops
Delta Logo
9:05 am - 10:36 pm
NAP
-
MDW
20h 31m
1 stop
$805Delta
Wed, Aug 19 - Wed, Aug 26
Delta Logo
6:05 am - 7:05 am
MDW
-
NAP
18h 00m
1 stop
Delta Logo
6:05 am - 6:33 pm
NAP
-
MDW
19h 28m
2 stops
$812Delta
Sun, Aug 9 - Tue, Aug 25
Delta Logo
9:24 am - 11:30 am
MDW
-
NAP
19h 06m
2 stops
Delta Logo
6:05 am - 6:01 pm
NAP
-
MDW
18h 56m
2 stops
$816Delta
Wed, Aug 19 - Wed, Aug 26
Delta Logo
6:05 am - 8:10 am
MDW
-
NAP
19h 05m
2 stops
Delta Logo
6:05 am - 6:33 pm
NAP
-
MDW
19h 28m
2 stops
$817Delta
Sun, Aug 9 - Tue, Aug 25
Air France Logo
1:25 pm - 10:35 am
MDW
-
NAP
14h 10m
2 stops
Air France Logo
6:05 am - 4:15 pm
NAP
-
MDW
17h 10m
2 stops
$821Air France
Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
6:30 pm - 3:50 pm
MDW
-
NAP
14h 20m
2 stops
Multiple Airlines Logo
11:20 am - 10:10 pm
NAP
-
MDW
17h 50m
2 stops
$827Multiple Airlines
Sun, Dec 13 - Thu, Jan 7
KLM Logo
5:10 pm - 7:05 am
MDW
-
NAP
30h 55m
1 stop
KLM Logo
9:05 am - 10:36 pm
NAP
-
MDW
20h 31m
1 stop
$840KLM
Mon, Aug 17 - Mon, Aug 24
Air France Logo
5:10 pm - 7:05 am
MDW
-
NAP
30h 55m
1 stop
Air France Logo
9:05 am - 10:36 pm
NAP
-
MDW
20h 31m
1 stop
$842Air France
Wed, Aug 19 - Wed, Aug 26

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Delta flights from Chicago Midway Airport to Naples

Our best Delta deals on Chicago Midway Airport to Naples flight tickets
Delta
Aug 19
MDW1:25 pmChicago Midway
15h 05m
2 stops
NAP11:30 amNaples
Aug 26
NAP9:05 amNaples
20h 31m
1 stop
MDW10:36 pmChicago Midway
$805
Delta
Aug 9
MDW6:05 amChicago Midway
18h 00m
1 stop
NAP7:05 amNaples
Aug 25
NAP6:05 amNaples
19h 28m
2 stops
MDW6:33 pmChicago Midway
$812
Delta
Aug 19
MDW9:24 amChicago Midway
19h 06m
2 stops
NAP11:30 amNaples
Aug 26
NAP6:05 amNaples
18h 56m
2 stops
MDW6:01 pmChicago Midway
$816

Air France flights from Chicago Midway Airport to Naples

Our best Air France deals on Chicago Midway Airport to Naples flight tickets
Air France
Aug 19
MDW1:25 pmChicago Midway
14h 10m
2 stops
NAP10:35 amNaples
Aug 26
NAP9:05 amNaples
20h 31m
1 stop
MDW10:36 pmChicago Midway
$801
Air France
Aug 18
MDW1:25 pmChicago Midway
14h 10m
2 stops
NAP10:35 amNaples
Aug 25
NAP6:05 amNaples
17h 10m
2 stops
MDW4:15 pmChicago Midway
$821
Air France
Aug 19
MDW5:10 pmChicago Midway
30h 55m
1 stop
NAP7:05 amNaples
Aug 26
NAP9:05 amNaples
20h 31m
1 stop
MDW10:36 pmChicago Midway
$842

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 July 8, 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

Cheapest round-trip

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/19

1:25 pm-10:35 am

2 stops14h 10m

Naples

Wed 8/26

9:05 am-10:36 pm

1 stop20h 31m

$801

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 8/9

6:05 am-7:05 am

1 stop18h 00m

Naples

Tue 8/25

6:05 am-4:15 pm

2 stops17h 10m

$804

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/19

1:25 pm-11:30 am

2 stops15h 05m

Naples

Wed 8/26

9:05 am-10:36 pm

1 stop20h 31m

$805

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 8/9

6:05 am-7:05 am

1 stop18h 00m

Naples

Tue 8/25

6:05 am-6:33 pm

2 stops19h 28m

$812

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/19

9:24 am-11:30 am

2 stops19h 06m

Naples

Wed 8/26

6:05 am-6:01 pm

2 stops18h 56m

$816

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 8/9

6:05 am-8:10 am

2 stops19h 05m

Naples

Tue 8/25

6:05 am-6:33 pm

2 stops19h 28m

$817
Quickest round-trip

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/18

1:25 pm-10:35 am

2 stops14h 10m

Naples

Tue 8/25

6:05 am-4:15 pm

2 stops17h 10m

$821

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 12/13

6:30 pm-3:50 pm

2 stops14h 20m

Naples

Thu 1/7

11:20 am-10:10 pm

2 stops17h 50m

$827

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 8/17

5:10 pm-7:05 am

1 stop30h 55m

Naples

Mon 8/24

9:05 am-10:36 pm

1 stop20h 31m

$840

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/19

5:10 pm-7:05 am

1 stop30h 55m

Naples

Wed 8/26

9:05 am-10:36 pm

1 stop20h 31m

$842

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 Sunday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $886. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Naples for around $1,235.

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 $908. In the afternoon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,224 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 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Naples takes 13h 10m
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

Frequently asked questions about flying from Chicago Midway Airport to Naples

  • 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 10m.

  • 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
Sorrento
Capri
Praiano
Ischia
Maiori
Ravello
Conca Dei Marini
Procida
Sant'Agnello
Caserta
Pompei
Anacapri
Furore
Massa Lubrense
Minori
Vietri sul Mare
Atrani
Ercolano

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.

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