Find Cheap Flights from Chicago Midway to Naples (MDW - NAP)

Search hundreds of travel sites at once for deals on flights to Naples

Fri 2/23
Fri 3/2
Any month
Compare vs. KAYAK |

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $864 or less.

FAQs for Booking Chicago Midway to Naples Flights

How long does a flight from Chicago Midway to Naples take?
An average nonstop flight takes 15h 43m, covering a distance of 4935 miles.
Which airlines provide the cheapest flights from Chicago Midway to Naples?
In the past 3 days, the cheapest round-trip tickets were found on KLM ($1222), Multiple Airlines ($1256) and Air France ($1256).
Do I need a passport to fly between Chicago Midway and Naples?
Yes.

Book cheap flights from Chicago Midway to Naples (round-trip)

Airports
Origin
Chicago
$1222
only
$1222
Destination
Naples
$1222
only
$1222
Wed, Apr 4
MDW
NAP
15h 43m
Thu, Apr 19
NAP
MDW
18h 44m
$1222
Trip: 16 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
AMS
TPE
Excellent 9.3

Service impeccable!

They have one line of executive class after the kitchen and toilet, is very noisy.

AMS
NCL
Good 7.6

Pretty basic one hour flight so there's not much to complain about or praise about. I got some sleep which was good.

The crew had their general Dutch aloofness on form. Chatted to one of the stewardesses in Dutch up until she saw I had a British passport then she decided she could only speak English to me.

PTY
AMS
Good 6.3

KLM crews look unhappy with their work. Everything they do is a favor not duty.

BCN
AMS
Excellent 9.3

The food was excelent

I have to pay to pay a little more confort

AMS
DTW
Mediocre 2.0

Amesterdam airport employee was really rude

Wed, Apr 11
MDW
NAP
16h 10m
Wed, Apr 18
NAP
MDW
23h 15m
$1256
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 21
MDW
NAP
15h 58m
Sat, Apr 28
NAP
MDW
23h 13m
$1256
Trip: 8 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 2195 reviews
Overall
7.6
Boarding
7.7
Comfort
7.3
Crew
8.2
Entertainment
6.8
Food
7.1
CDG
TXL
Excellent 10.0

Speed, professionalism

Nothing

CDG
MIA
Good 7.3

The airbus 380 was great and the staff very nice

Too mych bad smells after a few hours

BEY
CDG
Good 6.0

Nothing special

They start serving late the apperitif before taking off and take it back right after.

CAI
CDG
Mediocre 2.0

Its been a week. My trip has ended. I still do not have my bags. Terrible customer service.

CDG
BLL
Mediocre 2.0

Its been a week. My trip has ended. I still do not have my bags. Terrible customer service.

Tue, Apr 24
MDW
NAP
16h 10m
Tue, May 8
NAP
MDW
18h 38m
$1256
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
DTW
Excellent 10.0

I like service

GDL
ATL
Excellent 9.6

Expensive food

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

Tue, Apr 10
MDW
NAP
17h 42m
Thu, Apr 19
NAP
MDW
23h 15m
$1256
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
LAX
AMS
Mediocre 2.0

My bagage broke

I paid extra fee for extra bagage which was tv and i paid insurance my tv broke and no one responces for it

PTY
AMS
Good 6.3

KLM crews look unhappy with their work. Everything they do is a favor not duty.

AMS
LAX
Okay 4.0

The cabin crew were pretty good. That's about all that was good.

I paid almost $400 for upgraded seats. When I got to the airport-- no seats-- both ways!! i didn't even have regular seat assignments. I had to choose from the last few seats available. The ticket agent, the gate agent and the cabin crew all did nothing to make up for the fact that their system screwed up and stuck me in a cramped coach seat in the back of the plane for 11 hours-- TWICE! Beyond that, KLM must have one of the oldest fleets in the sky. Both ways LAX->AMS->LAX, I was on a 30-35 year old 747 with no wifi, no power and a ten-year-old entertainment system. Never again.

IAD
AMS
Mediocre 2.0

They stole my money

AMS
BLL
Good 6.5

Nice seats, comfortable.

Again, no aisle seat for SkyTeam Gold member. Also, my baggage was lost. First bag arrived a day late, second after I had left Billund and it was six days before the bag with my clothes reached me. I was told I will have 100 euro credit for clothing, but in the winter and for 6 days, this was not even close to the amount I needed for clothing and necessities, to have my time here.

Mon, Apr 16
MDW
NAP
16h 10m
Wed, May 2
NAP
MDW
23h 28m
$1256
Trip: 17 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 25
MDW
NAP
16h 10m
Wed, May 9
NAP
MDW
21h 07m
$1256
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

GDL
ATL
Excellent 9.6

Expensive food

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Thu, Apr 19
MDW
NAP
17h 42m
Sat, Apr 28
NAP
MDW
23h 13m
$1256
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
BCN
AMS
Excellent 9.3

The food was excelent

I have to pay to pay a little more confort

AMS
LAX
Okay 4.0

The cabin crew were pretty good. That's about all that was good.

I paid almost $400 for upgraded seats. When I got to the airport-- no seats-- both ways!! i didn't even have regular seat assignments. I had to choose from the last few seats available. The ticket agent, the gate agent and the cabin crew all did nothing to make up for the fact that their system screwed up and stuck me in a cramped coach seat in the back of the plane for 11 hours-- TWICE! Beyond that, KLM must have one of the oldest fleets in the sky. Both ways LAX->AMS->LAX, I was on a 30-35 year old 747 with no wifi, no power and a ten-year-old entertainment system. Never again.

AMS
NCL
Good 7.6

Pretty basic one hour flight so there's not much to complain about or praise about. I got some sleep which was good.

The crew had their general Dutch aloofness on form. Chatted to one of the stewardesses in Dutch up until she saw I had a British passport then she decided she could only speak English to me.

AMS
DTW
Mediocre 2.0

Amesterdam airport employee was really rude

IAD
AMS
Mediocre 2.0

They stole my money

Tue, May 1
MDW
NAP
16h 35m
Thu, May 10
NAP
MDW
23h 23m
$1256
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

JFK
CDG
Excellent 10.0

The food and the service

FLL
DTW
Excellent 10.0

I like service

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

GDL
ATL
Excellent 9.6

Expensive food

Sun, Apr 22
MDW
NAP
17h 42m
Tue, May 1
NAP
MDW
18h 43m
$1256
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
PTY
AMS
Good 6.3

KLM crews look unhappy with their work. Everything they do is a favor not duty.

AMS
LAX
Okay 4.0

The cabin crew were pretty good. That's about all that was good.

I paid almost $400 for upgraded seats. When I got to the airport-- no seats-- both ways!! i didn't even have regular seat assignments. I had to choose from the last few seats available. The ticket agent, the gate agent and the cabin crew all did nothing to make up for the fact that their system screwed up and stuck me in a cramped coach seat in the back of the plane for 11 hours-- TWICE! Beyond that, KLM must have one of the oldest fleets in the sky. Both ways LAX->AMS->LAX, I was on a 30-35 year old 747 with no wifi, no power and a ten-year-old entertainment system. Never again.

LAX
AMS
Mediocre 2.0

My bagage broke

I paid extra fee for extra bagage which was tv and i paid insurance my tv broke and no one responces for it

IAD
AMS
Mediocre 2.0

They stole my money

DMM
AMS
Okay 5.6

Tiny old cramped plane.

Sat, Apr 28
MDW
NAP
37h 15m
Tue, May 8
NAP
MDW
18h 38m
$1261
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

JFK
CDG
Excellent 10.0

The food and the service

Mon, Apr 23
MDW
NAP
15h 58m
Wed, May 2
NAP
MDW
23h 28m
$1256
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
IAD
AMS
Good 7.3

787 is a great airplane. The 3-3-3 seat configuration leaves enough seat width to be just comfortable in coach.

LAX
AMS
Mediocre 2.0

My bagage broke

I paid extra fee for extra bagage which was tv and i paid insurance my tv broke and no one responces for it

AMS
NCL
Good 7.6

Pretty basic one hour flight so there's not much to complain about or praise about. I got some sleep which was good.

The crew had their general Dutch aloofness on form. Chatted to one of the stewardesses in Dutch up until she saw I had a British passport then she decided she could only speak English to me.

AMS
DTW
Mediocre 2.0

Amesterdam airport employee was really rude

AMS
LAX
Okay 4.0

The cabin crew were pretty good. That's about all that was good.

I paid almost $400 for upgraded seats. When I got to the airport-- no seats-- both ways!! i didn't even have regular seat assignments. I had to choose from the last few seats available. The ticket agent, the gate agent and the cabin crew all did nothing to make up for the fact that their system screwed up and stuck me in a cramped coach seat in the back of the plane for 11 hours-- TWICE! Beyond that, KLM must have one of the oldest fleets in the sky. Both ways LAX->AMS->LAX, I was on a 30-35 year old 747 with no wifi, no power and a ten-year-old entertainment system. Never again.

Tue, May 1
MDW
NAP
43h 17m
Fri, May 11
NAP
MDW
33h 47m
$1262
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

GDL
ATL
Excellent 9.6

Expensive food

JFK
CDG
Excellent 10.0

The food and the service

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

Wed, Apr 11
MDW
NAP
19h 25m
Fri, Apr 20
NAP
MDW
23h 15m
$1261
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
DMM
AMS
Okay 5.6

Tiny old cramped plane.

AMS
DTW
Mediocre 2.0

Amesterdam airport employee was really rude

IAD
AMS
Mediocre 2.0

They stole my money

IAD
AMS
Good 7.3

787 is a great airplane. The 3-3-3 seat configuration leaves enough seat width to be just comfortable in coach.

AMS
BLL
Good 6.5

Nice seats, comfortable.

Again, no aisle seat for SkyTeam Gold member. Also, my baggage was lost. First bag arrived a day late, second after I had left Billund and it was six days before the bag with my clothes reached me. I was told I will have 100 euro credit for clothing, but in the winter and for 6 days, this was not even close to the amount I needed for clothing and necessities, to have my time here.

Tue, Apr 10
MDW
NAP
37h 31m
Fri, Apr 20
NAP
MDW
18h 39m
$1265
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

FLL
DTW
Excellent 10.0

I like service

GDL
ATL
Excellent 9.6

Expensive food

Thu, Apr 12
MDW
NAP
19h 25m
Fri, Apr 20
NAP
MDW
23h 15m
$1261
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
BCN
AMS
Excellent 9.3

The food was excelent

I have to pay to pay a little more confort

AMS
TPE
Excellent 9.3

Service impeccable!

They have one line of executive class after the kitchen and toilet, is very noisy.

AMS
BLL
Good 6.5

Nice seats, comfortable.

Again, no aisle seat for SkyTeam Gold member. Also, my baggage was lost. First bag arrived a day late, second after I had left Billund and it was six days before the bag with my clothes reached me. I was told I will have 100 euro credit for clothing, but in the winter and for 6 days, this was not even close to the amount I needed for clothing and necessities, to have my time here.

AMS
NCL
Good 7.6

Pretty basic one hour flight so there's not much to complain about or praise about. I got some sleep which was good.

The crew had their general Dutch aloofness on form. Chatted to one of the stewardesses in Dutch up until she saw I had a British passport then she decided she could only speak English to me.

TLV
AMS
Mediocre 2.0

Airlines issue

Profiling certain customers

Fri, Apr 13
MDW
NAP
39h 30m
Mon, Apr 23
NAP
MDW
18h 39m
$1265
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

FLL
DTW
Excellent 10.0

I like service

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

Fri, Apr 13
MDW
NAP
19h 13m
Sun, Apr 22
NAP
MDW
18h 44m
$1261
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
LAX
AMS
Mediocre 2.0

My bagage broke

I paid extra fee for extra bagage which was tv and i paid insurance my tv broke and no one responces for it

AMS
LAX
Okay 4.0

The cabin crew were pretty good. That's about all that was good.

I paid almost $400 for upgraded seats. When I got to the airport-- no seats-- both ways!! i didn't even have regular seat assignments. I had to choose from the last few seats available. The ticket agent, the gate agent and the cabin crew all did nothing to make up for the fact that their system screwed up and stuck me in a cramped coach seat in the back of the plane for 11 hours-- TWICE! Beyond that, KLM must have one of the oldest fleets in the sky. Both ways LAX->AMS->LAX, I was on a 30-35 year old 747 with no wifi, no power and a ten-year-old entertainment system. Never again.

AMS
BLL
Good 6.5

Nice seats, comfortable.

Again, no aisle seat for SkyTeam Gold member. Also, my baggage was lost. First bag arrived a day late, second after I had left Billund and it was six days before the bag with my clothes reached me. I was told I will have 100 euro credit for clothing, but in the winter and for 6 days, this was not even close to the amount I needed for clothing and necessities, to have my time here.

IAD
AMS
Good 7.3

787 is a great airplane. The 3-3-3 seat configuration leaves enough seat width to be just comfortable in coach.

AMS
NCL
Good 7.6

Pretty basic one hour flight so there's not much to complain about or praise about. I got some sleep which was good.

The crew had their general Dutch aloofness on form. Chatted to one of the stewardesses in Dutch up until she saw I had a British passport then she decided she could only speak English to me.

Fri, Apr 20
MDW
NAP
37h 31m
Mon, Apr 30
NAP
MDW
18h 39m
$1265
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

FLL
DTW
Excellent 10.0

I like service

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Sat, Apr 14
MDW
NAP
19h 10m
Mon, Apr 23
NAP
MDW
23h 15m
$1261
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 1756 reviews
Overall
8.0
Boarding
7.9
Comfort
7.7
Crew
8.4
Entertainment
7.1
Food
7.4
LAX
AMS
Mediocre 2.0

My bagage broke

I paid extra fee for extra bagage which was tv and i paid insurance my tv broke and no one responces for it

BCN
AMS
Excellent 9.3

The food was excelent

I have to pay to pay a little more confort

AMS
BLL
Good 6.5

Nice seats, comfortable.

Again, no aisle seat for SkyTeam Gold member. Also, my baggage was lost. First bag arrived a day late, second after I had left Billund and it was six days before the bag with my clothes reached me. I was told I will have 100 euro credit for clothing, but in the winter and for 6 days, this was not even close to the amount I needed for clothing and necessities, to have my time here.

PTY
AMS
Good 6.3

KLM crews look unhappy with their work. Everything they do is a favor not duty.

TLV
AMS
Mediocre 2.0

Airlines issue

Profiling certain customers

Chicago Midway to Naples Flight Information

Flights Arrive in Naples
Flights Depart from Chicago Midway
Flight Price $1222
Distance 4935 miles
Airlines KLM, Air France, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.