Find Cheap Flights from Chicago Midway to Kailua-Kona (MDW - KOA)

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Looking for a cheap flight? 25% of our users found flights on this route for $815 or less.

FAQs for Booking Chicago Midway to Kailua-Kona Flights

How long does a flight from Chicago Midway to Kailua-Kona take?
An average nonstop flight takes 13h 57m, covering a distance of 4216 miles.
Which airlines provide the cheapest flights from Chicago Midway to Kailua-Kona?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($701)
Do I need a passport to fly between Chicago Midway and Kailua-Kona?
No.

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

Airports
Origin
Chicago
$701
only
$701
Destination
Kailua-Kona
$701
only
$701
Mon, Apr 16
MDW
KOA
13h 57m
Thu, Apr 26
KOA
MDW
12h 35m
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
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Tue, Apr 17
MDW
KOA
14h 52m
Thu, Apr 26
KOA
MDW
15h 14m
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
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Mediocre 2.0

Delayed

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Wed, Apr 18
MDW
KOA
13h 57m
Thu, Apr 26
KOA
MDW
15h 14m
Trip: 9 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
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

MSP
CLT
Mediocre 2.0

Delayed

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

Thu, Apr 19
MDW
KOA
15h 44m
Thu, Apr 26
KOA
MDW
12h 35m
Trip: 8 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
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Mediocre 2.0

Delayed

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Mon, Apr 23
MDW
KOA
14h 52m
Thu, May 3
KOA
MDW
12h 17m
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
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

SLC
YYZ
Excellent 9.6

Z

Tue, Apr 24
MDW
KOA
14h 52m
Thu, May 3
KOA
MDW
12h 17m
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
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

MSP
CLT
Mediocre 2.0

Delayed

Wed, Apr 25
MDW
KOA
13h 57m
Mon, May 7
KOA
MDW
12h 17m
Trip: 13 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
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 9.6

Z

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

Thu, Apr 26
MDW
KOA
13h 57m
Mon, May 7
KOA
MDW
14h 26m
Trip: 12 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
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

SLC
YYZ
Excellent 9.6

Z

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Mon, Apr 30
MDW
KOA
15h 44m
Mon, May 7
KOA
MDW
13h 24m
Trip: 8 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
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

MSP
CLT
Mediocre 2.0

Delayed

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

Tue, May 1
MDW
KOA
13h 58m
Mon, May 7
KOA
MDW
13h 43m
Trip: 7 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
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

SLC
YYZ
Excellent 9.6

Z

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Tue, May 15
MDW
KOA
15h 36m
Tue, May 22
KOA
MDW
12h 17m
Trip: 8 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
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Wed, May 16
MDW
KOA
15h 36m
Tue, May 22
KOA
MDW
12h 17m
Trip: 7 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
AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

MSP
CLT
Mediocre 2.0

Delayed

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

Mon, May 21
MDW
KOA
15h 36m
Tue, May 29
KOA
MDW
12h 17m
Trip: 9 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
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Mediocre 2.0

Delayed

Wed, May 23
MDW
KOA
15h 36m
Mon, Jun 4
KOA
MDW
13h 24m
Trip: 13 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
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Mon, Apr 16
MDW
KOA
13h 57m
Thu, Apr 26
KOA
MDW
12h 35m
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
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

AMS
JFK
Excellent 8.3

The seat in Comfort+ was comfortable. The crew was very professional and also friendly and pleasant. The flight departed on time and arrived early.

Food was mediocre.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

Wed, Apr 18
MDW
KOA
15h 44m
Thu, Apr 26
KOA
MDW
14h 10m
Trip: 9 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
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Mediocre 2.0

Delayed

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

Mon, Apr 9
MDW
KOA
15h 31m
Mon, Apr 23
KOA
MDW
14h 29m
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
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CLT
Mediocre 2.0

Delayed

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

Wed, Apr 11
MDW
KOA
15h 44m
Wed, Apr 25
KOA
MDW
14h 10m
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
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

SLC
YYZ
Excellent 9.6

Z

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Thu, Apr 12
MDW
KOA
15h 44m
Wed, Apr 25
KOA
MDW
14h 29m
Trip: 14 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
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

Mon, Apr 23
MDW
KOA
14h 52m
Wed, May 2
KOA
MDW
13h 24m
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
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

ATL
MDW
Okay 4.6

Flight delayed 2 hrs

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Chicago Midway to Kailua-Kona Flight Information

Flights Arrive in Kailua-Kona
Flights Depart from Chicago Midway
Flight Price $701
Distance 4216 miles
Airlines Delta
*
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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.