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Cheap flights from Chicago Midway Airport to Naples from $250

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 10/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Naples (MDW-NAP)

Cheap round-trip flights

Delta Logo
2:00 pm - 11:30 amMDW-NAP
14h 30m2 stops
Delta Logo
6:15 am - 6:34 pmNAP-MDW
19h 19m2 stops
$640Delta
Find Deal
dom., feb. 8 - jue., feb. 19
Delta Logo
10:35 am - 11:30 amMDW-NAP
17h 55m2 stops
Delta Logo
12:15 pm - 6:08 pmNAP-MDW
36h 53m2 stops
$653Delta
Find Deal
dom., feb. 8 - lun., feb. 16
Air France Logo
2:00 pm - 11:30 amMDW-NAP
14h 30m2 stops
Air France Logo
6:15 am - 6:34 pmNAP-MDW
19h 19m2 stops
$665Air France
Find Deal
mié., feb. 11 - jue., feb. 19
Delta Logo
1:00 pm - 11:10 amMDW-NAP
15h 10m2 stops
Delta Logo
6:15 am - 6:36 pmNAP-MDW
19h 21m2 stops
$666Delta
Find Deal
mié., dic. 3 - mié., dic. 10
Air France Logo
2:00 pm - 11:30 amMDW-NAP
14h 30m2 stops
Air France Logo
6:15 am - 6:08 pmNAP-MDW
18h 53m2 stops
$690Air France
Find Deal
mié., feb. 11 - mar., feb. 17
Air France Logo
10:35 am - 7:00 amMDW-NAP
13h 25m1 stop
Air France Logo
6:15 am - 6:25 pmNAP-MDW
19h 10m2 stops
$691Air France
Find Deal
mié., oct. 22 - vie., nov. 7
Delta Logo
9:35 am - 7:00 amMDW-NAP
14h 25m2 stops
Delta Logo
6:15 am - 5:43 pmNAP-MDW
18h 28m2 stops
$696Delta
Find Deal
mié., oct. 22 - vie., nov. 7
Delta Logo
6:23 pm - 9:15 pmMDW-NAP
20h 52m2 stops
Delta Logo
6:15 am - 6:25 pmNAP-MDW
19h 10m2 stops
$710Delta
Find Deal
lun., oct. 27 - vie., nov. 7
KLM Logo
6:00 am - 7:00 amMDW-NAP
18h 00m1 stop
KLM Logo
9:00 am - 5:35 pmNAP-MDW
15h 35m1 stop
$981KLM
Find Deal
lun., sep. 8 - mar., sep. 16
KLM Logo
6:00 am - 7:00 amMDW-NAP
18h 00m1 stop
KLM Logo
9:00 am - 9:36 pmNAP-MDW
19h 36m1 stop
$1,031KLM
Find Deal
lun., sep. 8 - mar., sep. 23

Delta flights from Chicago Midway Airport to Naples

Our best Delta deals on Chicago Midway Airport to Naples flight tickets
Delta
Feb 8
MDW2:00 pmChicago Midway
14h 30m
2 stops
NAP11:30 amNaples
Feb 19
NAP6:15 amNaples
19h 19m
2 stops
MDW6:34 pmChicago Midway
$640
Find similar
Delta
Feb 8
MDW10:35 amChicago Midway
17h 55m
2 stops
NAP11:30 amNaples
Feb 16
NAP12:15 pmNaples
36h 53m
2 stops
MDW6:08 pmChicago Midway
$653
Find similar
Delta
Dec 3
MDW1:00 pmChicago Midway
15h 10m
2 stops
NAP11:10 amNaples
Dec 10
NAP6:15 amNaples
19h 21m
2 stops
MDW6:36 pmChicago Midway
$666
Find similar

Air France flights from Chicago Midway Airport to Naples

Our best Air France deals on Chicago Midway Airport to Naples flight tickets
Air France
Feb 11
MDW2:00 pmChicago Midway
14h 30m
2 stops
NAP11:30 amNaples
Feb 19
NAP6:15 amNaples
19h 19m
2 stops
MDW6:34 pmChicago Midway
$665
Find similar
Air France
Feb 11
MDW2:00 pmChicago Midway
14h 30m
2 stops
NAP11:30 amNaples
Feb 17
NAP6:15 amNaples
18h 53m
2 stops
MDW6:08 pmChicago Midway
$690
Find similar
Air France
Oct 22
MDW10:35 amChicago Midway
13h 25m
1 stop
NAP7:00 amNaples
Nov 7
NAP6:15 amNaples
19h 10m
2 stops
MDW6:25 pmChicago Midway
$691
Find similar

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 agosto 18, 2025.
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

dom. 2/8

2:00 pm-11:30 am

2 stops14h 30m

Naples

jue. 2/19

6:15 am-6:34 pm

2 stops19h 19m

$640

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

dom. 2/8

10:35 am-11:30 am

2 stops17h 55m

Naples

lun. 2/16

12:15 pm-6:08 pm

2 stops36h 53m

$653

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

mié. 2/11

2:00 pm-11:30 am

2 stops14h 30m

Naples

jue. 2/19

6:15 am-6:34 pm

2 stops19h 19m

$665

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

mié. 12/3

1:00 pm-11:10 am

2 stops15h 10m

Naples

mié. 12/10

6:15 am-6:36 pm

2 stops19h 21m

$666

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

mié. 2/11

2:00 pm-11:30 am

2 stops14h 30m

Naples

mar. 2/17

6:15 am-6:08 pm

2 stops18h 53m

$690

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

mié. 10/22

10:35 am-7:00 am

1 stop13h 25m

Naples

vie. 11/7

6:15 am-6:25 pm

2 stops19h 10m

$691

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

mié. 10/22

9:35 am-7:00 am

2 stops14h 25m

Naples

vie. 11/7

6:15 am-5:43 pm

2 stops18h 28m

$696

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

lun. 10/27

6:23 pm-9:15 pm

2 stops20h 52m

Naples

vie. 11/7

6:15 am-6:25 pm

2 stops19h 10m

$710

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

lun. 9/8

6:00 am-7:00 am

1 stop18h 00m

Naples

mar. 9/16

9:00 am-5:35 pm

1 stop15h 35m

$981

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

lun. 9/8

6:00 am-7:00 am

1 stop18h 00m

Naples

mar. 9/23

9:00 am-9:36 pm

1 stop19h 36m

$1,031

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 Monday is the least expensive day to fly to Naples. Tickets to fly out on this day can be as low as $1,005. 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 $1,273.

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 morning. Our users have found flights to Naples in the morning for as low as $705. At noon is when there is more demand to fly to Naples, so prices are often more expensive at around $1,228 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

Best Price Found

$250

Fastest flight time

13h 25m

Direct flights

None

Airports in Naples

1 airport
The best one-way flight to Naples from Chicago Midway Airport in the past 72 hours is $250. The best round-trip flight deal from Chicago Midway Airport to Naples found on momondo in the last 72 hours is $640.
The fastest flight from Chicago Midway Airport to Naples takes 13h 25m
There are no direct flights from Chicago Midway Airport to Naples. Popular non-direct route for this connection is Chicago Midway Airport - Naples Airport.
There is 1 airport near Naples: Naples (NAP)
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 25m.

  • 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
Capri
Sorrento
Positano
Praiano
Ravello
Ischia
Pompei
Maiori
Minori
Sant'Agnello
Ercolano
Procida
Vico Equense
Atrani
Nola
Anacapri
Vietri sul Mare
Furore
Caserta

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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