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Cheap flights from Chicago Midway Airport to Naples from $471

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 7/4. 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

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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.
Delta Logo
10:35 am - 7:05 am
MDW
-
NAP
13h 30m
1 stop
Delta Logo
6:05 am - 6:05 pm
NAP
-
MDW
19h 00m
2 stops
$775Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
10:35 am - 7:05 am
MDW
-
NAP
13h 30m
1 stop
Delta Logo
6:05 am - 9:46 pm
NAP
-
MDW
22h 41m
2 stops
$776Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
10:35 am - 11:30 am
MDW
-
NAP
17h 55m
2 stops
Delta Logo
6:05 am - 6:05 pm
NAP
-
MDW
19h 00m
2 stops
$779Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
10:35 am - 11:30 am
MDW
-
NAP
17h 55m
2 stops
Delta Logo
6:05 am - 4:27 pm
NAP
-
MDW
17h 22m
2 stops
$780Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
10:35 am - 11:30 am
MDW
-
NAP
17h 55m
2 stops
Delta Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$817Delta
Wed, Aug 12 - Fri, Aug 21
Delta Logo
1:00 pm - 11:30 am
MDW
-
NAP
15h 30m
2 stops
Delta Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$867Delta
Wed, Aug 12 - Fri, Aug 21
KLM Logo
5:25 pm - 7:05 am
MDW
-
NAP
30h 40m
1 stop
KLM Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$870KLM
Wed, Aug 12 - Fri, Aug 21
KLM Logo
5:25 pm - 7:05 am
MDW
-
NAP
30h 40m
1 stop
KLM Logo
9:05 am - 9:46 pm
NAP
-
MDW
19h 41m
1 stop
$920KLM
Wed, Aug 12 - Fri, Aug 21
Delta Logo
11:05 am - 7:05 am
MDW
-
NAP
13h 00m
1 stop
Delta Logo
6:05 am - 6:31 pm
NAP
-
MDW
19h 26m
2 stops
$926Delta
Tue, Jul 28 - Tue, Aug 25
Delta Logo
5:10 pm - 6:15 pm
MDW
-
NAP
18h 05m
2 stops
Delta Logo
6:05 am - 9:46 pm
NAP
-
MDW
22h 41m
2 stops
$930Delta
Tue, Jul 28 - Tue, Aug 25

Delta flights from Chicago Midway Airport to Naples

Our best Delta deals on Chicago Midway Airport to Naples flight tickets
Delta
Aug 18
MDW10:35 amChicago Midway
13h 30m
1 stop
NAP7:05 amNaples
Aug 25
NAP6:05 amNaples
19h 00m
2 stops
MDW6:05 pmChicago Midway
$775
Delta
Aug 18
MDW10:35 amChicago Midway
13h 30m
1 stop
NAP7:05 amNaples
Aug 25
NAP6:05 amNaples
22h 41m
2 stops
MDW9:46 pmChicago Midway
$776
Delta
Aug 18
MDW10:35 amChicago Midway
17h 55m
2 stops
NAP11:30 amNaples
Aug 25
NAP6:05 amNaples
19h 00m
2 stops
MDW6:05 pmChicago Midway
$779

KLM flights from Chicago Midway Airport to Naples

Our best KLM deals on Chicago Midway Airport to Naples flight tickets
KLM
Aug 12
MDW5:25 pmChicago Midway
30h 40m
1 stop
NAP7:05 amNaples
Aug 21
NAP9:05 amNaples
19h 41m
1 stop
MDW9:46 pmChicago Midway
$870
KLM
Aug 12
MDW5:25 pmChicago Midway
30h 40m
1 stop
NAP7:05 amNaples
Aug 21
NAP9:05 amNaples
19h 41m
1 stop
MDW9:46 pmChicago Midway
$920
KLM
May 6
MDW1:24 pmChicago Midway
19h 21m
2 stops
NAP3:45 pmNaples
May 20
NAP6:35 amNaples
18h 58m
2 stops
MDW6:33 pmChicago Midway
$1,123

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 April 2, 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 8/18

10:35 am-7:05 am

1 stop13h 30m

Naples

Tue 8/25

6:05 am-6:05 pm

2 stops19h 00m

$775

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/18

10:35 am-7:05 am

1 stop13h 30m

Naples

Tue 8/25

6:05 am-9:46 pm

2 stops22h 41m

$776

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/18

10:35 am-11:30 am

2 stops17h 55m

Naples

Tue 8/25

6:05 am-6:05 pm

2 stops19h 00m

$779

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 8/18

10:35 am-11:30 am

2 stops17h 55m

Naples

Tue 8/25

6:05 am-4:27 pm

2 stops17h 22m

$780

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

10:35 am-11:30 am

2 stops17h 55m

Naples

Fri 8/21

9:05 am-9:46 pm

1 stop19h 41m

$817

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

1:00 pm-11:30 am

2 stops15h 30m

Naples

Fri 8/21

9:05 am-9:46 pm

1 stop19h 41m

$867

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

5:25 pm-7:05 am

1 stop30h 40m

Naples

Fri 8/21

9:05 am-9:46 pm

1 stop19h 41m

$870

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 8/12

5:25 pm-7:05 am

1 stop30h 40m

Naples

Fri 8/21

9:05 am-9:46 pm

1 stop19h 41m

$920
Quickest round-trip

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 7/28

11:05 am-7:05 am

1 stop13h 00m

Naples

Tue 8/25

6:05 am-6:31 pm

2 stops19h 26m

$926

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Tue 7/28

5:10 pm-6:15 pm

2 stops18h 05m

Naples

Tue 8/25

6:05 am-9:46 pm

2 stops22h 41m

$930

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 Tuesday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $878. 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 $971. In the afternoon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,142 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
Capri
Sorrento
Praiano
Ravello
Ischia
Maiori
Sant'Agnello
Pompei
Procida
Minori
Vietri sul Mare
Anacapri
Furore
Atrani
Nola
Ercolano
Conca Dei Marini
Piano di Sorrento

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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