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Cheap flights from Chicago Midway Airport to Naples from $415

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 9/30. 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

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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
10:35 am - 7:05 am
MDW
-
NAP
13h 30m
1 stop
KLM Logo
9:05 am - 9:45 pm
NAP
-
MDW
19h 40m
1 stop
$911KLM
Tue, Oct 13 - Wed, Oct 21
Delta Logo
12:30 pm - 11:30 am
MDW
-
NAP
16h 00m
2 stops
Delta Logo
9:05 am - 9:45 pm
NAP
-
MDW
19h 40m
1 stop
$915Delta
Tue, Oct 13 - Wed, Oct 21
Delta Logo
6:00 am - 8:10 am
MDW
-
NAP
19h 10m
2 stops
Delta Logo
9:05 am - 9:45 pm
NAP
-
MDW
19h 40m
1 stop
$916Delta
Tue, Oct 13 - Wed, Oct 21
Multiple Airlines Logo
6:45 pm - 3:50 pm
MDW
-
NAP
15h 05m
2 stops
Multiple Airlines Logo
11:20 am - 9:45 pm
NAP
-
MDW
17h 25m
2 stops
$925Multiple Airlines
Tue, Oct 27 - Wed, Nov 4
Delta Logo
9:30 am - 7:05 am
MDW
-
NAP
14h 35m
2 stops
Delta Logo
6:05 am - 4:50 pm
NAP
-
MDW
17h 45m
2 stops
$928Delta
Tue, Oct 13 - Wed, Oct 21
KLM Logo
5:25 pm - 7:05 am
MDW
-
NAP
30h 40m
1 stop
KLM Logo
9:05 am - 9:45 pm
NAP
-
MDW
19h 40m
1 stop
$1,031KLM
Mon, Oct 12 - Mon, Oct 19
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
NAP
18h 05m
1 stop
Multiple Airlines Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$1,044Multiple Airlines
Sat, Sep 19 - Mon, Oct 5
KLM Logo
10:35 am - 7:05 am
MDW
-
NAP
13h 30m
1 stop
KLM Logo
6:35 am - 6:37 pm
NAP
-
MDW
18h 02m
2 stops
$1,049KLM
Sun, Oct 18 - Wed, Oct 28
Delta Logo
10:35 am - 7:05 am
MDW
-
NAP
13h 30m
1 stop
Delta Logo
9:05 am - 9:45 pm
NAP
-
MDW
19h 40m
1 stop
$1,061Delta
Tue, Oct 6 - Wed, Oct 21
Delta Logo
10:35 am - 11:30 am
MDW
-
NAP
17h 55m
2 stops
Delta Logo
9:05 am - 9:45 pm
NAP
-
MDW
19h 40m
1 stop
$1,065Delta
Wed, Oct 7 - Wed, Oct 21

Delta flights from Chicago Midway Airport to Naples

Our best Delta deals on Chicago Midway Airport to Naples flight tickets
Delta
Oct 13
MDW12:30 pmChicago Midway
16h 00m
2 stops
NAP11:30 amNaples
Oct 21
NAP9:05 amNaples
19h 40m
1 stop
MDW9:45 pmChicago Midway
$915
Delta
Oct 13
MDW6:00 amChicago Midway
19h 10m
2 stops
NAP8:10 amNaples
Oct 21
NAP9:05 amNaples
19h 40m
1 stop
MDW9:45 pmChicago Midway
$916
Delta
Oct 13
MDW9:30 amChicago Midway
14h 35m
2 stops
NAP7:05 amNaples
Oct 21
NAP6:05 amNaples
17h 45m
2 stops
MDW4:50 pmChicago Midway
$928

KLM flights from Chicago Midway Airport to Naples

Our best KLM deals on Chicago Midway Airport to Naples flight tickets
KLM
Oct 13
MDW10:35 amChicago Midway
13h 30m
1 stop
NAP7:05 amNaples
Oct 21
NAP9:05 amNaples
19h 40m
1 stop
MDW9:45 pmChicago Midway
$911
KLM
Oct 12
MDW5:25 pmChicago Midway
30h 40m
1 stop
NAP7:05 amNaples
Oct 19
NAP9:05 amNaples
19h 40m
1 stop
MDW9:45 pmChicago Midway
$1,031
KLM
Oct 18
MDW10:35 amChicago Midway
13h 30m
1 stop
NAP7:05 amNaples
Oct 28
NAP6:35 amNaples
18h 02m
2 stops
MDW6:37 pmChicago Midway
$1,049

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 May 23, 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

Tue 10/13

10:35 am-7:05 am

1 stop13h 30m

Naples

Wed 10/21

9:05 am-9:45 pm

1 stop19h 40m

$911

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/13

12:30 pm-11:30 am

2 stops16h 00m

Naples

Wed 10/21

9:05 am-9:45 pm

1 stop19h 40m

$915

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/13

6:00 am-8:10 am

2 stops19h 10m

Naples

Wed 10/21

9:05 am-9:45 pm

1 stop19h 40m

$916

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/27

6:45 pm-3:50 pm

2 stops15h 05m

Naples

Wed 11/4

11:20 am-9:45 pm

2 stops17h 25m

$925

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/13

9:30 am-7:05 am

2 stops14h 35m

Naples

Wed 10/21

6:05 am-4:50 pm

2 stops17h 45m

$928

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Mon 10/12

5:25 pm-7:05 am

1 stop30h 40m

Naples

Mon 10/19

9:05 am-9:45 pm

1 stop19h 40m

$1,031

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 9/19

6:00 am-7:05 am

1 stop18h 05m

Naples

Mon 10/5

9:05 am-9:46 pm

1 stop19h 41m

$1,044
Quickest round-trip

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sun 10/18

10:35 am-7:05 am

1 stop13h 30m

Naples

Wed 10/28

6:35 am-6:37 pm

2 stops18h 02m

$1,049

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 10/6

10:35 am-7:05 am

1 stop13h 30m

Naples

Wed 10/21

9:05 am-9:45 pm

1 stop19h 40m

$1,061

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 10/7

10:35 am-11:30 am

2 stops17h 55m

Naples

Wed 10/21

9:05 am-9:45 pm

1 stop19h 40m

$1,065

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 $880. 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 $864. In the afternoon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,233 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 00m

Direct flights

None
The fastest flight from Chicago Midway Airport to Naples takes 13h 00m
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 00m.

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

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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