Find cheap flights from Chicago Midway Airport to Kailua-Kona

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MDW — KOA
Jun 24 — Jul 11
Round-trip
1 adult
Economy
0 bags
From?
To?
Fri 6/24
Fri 7/1

When to book flights from Chicago Midway Airport to Kona Intl

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight from MDW to Kailua-Kona

  • Morning departure is around 30% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago Midway Airport to Kailua-Kona flights

Top airline flying Chicago Midway to Kona Intl

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 30918 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

After a delay, the flight departed and it was a smooth flight. Good service from the flight crew and we arrived home nearly on time.

Read more about Delta

After a delay, the flight departed and it was a smooth flight. Good service from the flight crew and we arrived home nearly on time.

Flight was canceled due to damaged aircraft

More upbeat team at board warm boarding crew but not as upbeat as they need to be in my opinion

Service Excellent

Had a crying baby the whole flight. When we arrived at the gate we had to wait for the gangway.

The TSA screening is absolutely unnecessary. It is dehumanizing and has been proven to be in-effective!

Pros: "Very comfortable"
Pros: "The best"
Cons: "Nothing"
Cons: "Always delays , three times late before took off and than while landing ! First class seat and seat tray don’t close , tv doesn’t work how it suppose too"
Pros: "Great entertainment features and free drinks."
Cons: "Ran out of certain types of food"
Pros: "The poor cabin stewardess was working the whole time as it was a short flight."
Cons: "This is a horrible route, they charge you more than flying to Europe and give you a one hour ride in a cramped plane where you can't even bring in a carry-on. The cost is insane but is one of the reasons Wall Street loves Delta as they are racking in the profits for very little service."
Pros: "Connecting flight attendant was extremely helpful"
Cons: "Delayed due to weather this missed the first connection then bumped from first class by a rude gate agent in Atlanta"
Pros: "There was an available seat next to me"
Cons: "I had to walk from one end of Minneapolis airport to the other end all within 35 mins to catch a connecting flight, tram was not in service. Not fun!!!"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Food was great. Especially the ice cream."
Pros: "Loved the plane, people and timeliness"
Pros: "Crew had pleasant personalities.. not stoic annoyed faces"
Cons: "People should wait their turn getting off the planes “Wait until the seat in front of you is empty,” says the elementary school teacher .."
Pros: "Nothing"
Cons: "Everything. Awful plane, seats and service"
Cons: "Seat assignment at gate and it changed 3 times to Accommodate others."
Cons: "Leg room"
Cons: "At least one hour late"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Pros: "2: 1/2 delay"
Cons: "They put us on the plane after waiting 11/2 hours, we all had to deplane as the mechanical problems were not done correctly. We waited another hour to correct before leaving. The gate agent was able to get me on a later connecting flight to Charleston. That was a positive."
Pros: "Great customer service. Crew was super friendly and flight was smooth and on time."
Pros: "Crew was friendly, flight ran on time."
Cons: "Can you make the seats any smaller? Cabin space is tight and for people who suffer from claustrophobia it makes it difficult traveling. More cabin space with raising the fares would be great!"
Cons: "Cabin was too hot since the very beginning. Even in first class."
Cons: "Security in PRG was little bit strong They ask my about my last job - 15 years ago if I did not fight with my Manager(I forgat his name)"
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "The flight was on time. Airport personnel were courteous & efficient. Airplane was clean. Pilot was friendly. A passenger had a peanut allergy so Delta distributed almonds, instead. Nice. Overall, I like Delta."
Cons: "Leg room was just barely adequate. It was a small plane-nothing could be done about that."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Cons: "Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight."
Pros: "Was switched to United airlines by delta due to plane issues. Houston to Laf"
Pros: "Movie"
Cons: "Break downs again... At least this time they found another plane."
Pros: "Zones are more delineated."
Cons: "People were obviously cutting in line and edging up before their zones were called."
Pros: "Nice smooth flight"
Pros: "The boarding agents were especially helpful and friendly to my disabled wife, travelling in a wheelchair."
Pros: "Entertainment system was good, great crew, great food, great service"
Cons: "Airplanes are filthy; asked for Coke without ice & the flight attendant filled my cup halfway. Unbelievably cheap! I was afraid to ask for more, for fear that I'd get an up charge!"
Pros: "Crew smiling at the end of the flight."
Cons: "Cheap coffee (although it says Starbucks, I have tried better)."
Pros: "I'm not sure but it seemed as though the isle was wider than before or other airlines. It looks as nice not having the beverage cart hit my elbow when it went down the isle."
Pros: "I got home. That's the highlight. We didn't have any incidents."
Cons: "Took off late because the bus to transport flight attendants were late. Backed up once into New York. Had to circle several times. Once landed we waited in a queue behind 10 aircraft."
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Pros: "Crew was great. The video game quiz re knowledge of cities worldwide was entertaining and educational"
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."
Cons: "For some reason I had to get my seat at the gate and waste extra time for it"
Pros: "I like the fact that I was able to get on this"
Cons: "Delta is completely messed up. My luggage was supposed to travel with me to Boston. But it didn't. Delta waisted my time. Horrible customer su"
Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."
Cons: "The flight aborted landing in Sun Valley. The reason is because the airplane you send there can only land in a 10 Kt tail wind. This is unacceptable, number one, but if you insist on using this aircraft you should at least have a shuttle available for us from the diverting airport in Twin Falls or perhaps just quit serving Haley and just serve an airport that you can land in with great regularity again this is unacceptable and will certainly mean that I think twice about using Delta in the future."
Cons: "No meals was available for VEG. people."
Pros: "Staff of KLM were friendly."
Cons: "Despite checking in online and selecting a window seat, I ended up in the middle seat of the middle row with two large neighbours and I had half of each in my seat."
COVID-19 information

Safety measures for airlines flying from Chicago Midway Airport to Kailua-Kona

Airlines flying from Chicago Midway Airport to Kailua-Kona have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago Midway Airport to Kailua-Kona

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway Airport to Kailua-Kona

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway Airport to Kailua-Kona

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway Airport to Kailua-Kona

Flexible cancellations

Waiving of change fees. Search flexible flights from Chicago Midway Airport to Kailua-Kona

Book cheap flights from Chicago Midway Airport to Kailua-Kona

Recent round-trip flight deals

10/26Wed
2 stopsDelta
28h 36mMDW-KOA
11/4Fri
2 stopsDelta
17h 57mKOA-MDW
$609
12/5Mon
2 stopsDelta
27h 33mMDW-KOA
12/13Tue
2 stopsDelta
21h 59mKOA-MDW
$623
10/30Sun
2 stopsDelta
28h 36mMDW-KOA
11/8Tue
2 stopsDelta
16h 26mKOA-MDW
$640
10/25Tue
2 stopsDelta
28h 36mMDW-KOA
11/2Wed
2 stopsDelta
16h 59mKOA-MDW
$647
11/1Tue
2 stopsDelta
30h 18mMDW-KOA
11/9Wed
2 stopsDelta
18h 07mKOA-MDW
$667
11/8Tue
2 stopsDelta
14h 18mMDW-KOA
11/16Wed
2 stopsDelta
18h 07mKOA-MDW
$669
11/2Wed
2 stopsDelta
17h 33mMDW-KOA
11/9Wed
2 stopsDelta
18h 07mKOA-MDW
$721
11/29Tue
2 stopsDelta
27h 33mMDW-KOA
12/7Wed
2 stopsDelta
18h 07mKOA-MDW
$727
12/7Wed
2 stopsDelta
14h 17mMDW-KOA
12/14Wed
2 stopsDelta
13h 25mKOA-MDW
$751
11/7Mon
2 stopsDelta
28h 43mMDW-KOA
11/16Wed
2 stopsDelta
17h 20mKOA-MDW
$753
11/14Mon
2 stopsDelta
27h 48mMDW-KOA
11/23Wed
2 stopsDelta
21h 55mKOA-MDW
$757
12/11Sun
2 stopsDelta
28h 42mMDW-KOA
12/20Tue
2 stopsDelta
21h 23mKOA-MDW
$809
7/11Mon
3 stopsMultiple Airlines
29h 24mMDW-KOA
7/15Fri
2 stopsMultiple Airlines
22h 20mKOA-MDW
$838
8/30Tue
2 stopsDelta
16h 32mMDW-KOA
9/7Wed
2 stopsDelta
14h 32mKOA-MDW
$858
8/24Wed
2 stopsDelta
14h 13mMDW-KOA
8/29Mon
2 stopsDelta
16h 17mKOA-MDW
$880
10/26Wed
2 stopsDelta
14h 11mMDW-KOA
11/2Wed
2 stopsDelta
16h 01mKOA-MDW
$909
10/29Sat
2 stopsDelta
14h 11mMDW-KOA
11/5Sat
2 stopsDelta
16h 26mKOA-MDW
$946
12/5Mon
2 stopsDelta
14h 17mMDW-KOA
12/12Mon
2 stopsDelta
15h 03mKOA-MDW
$964
11/4Fri
2 stopsDelta
17h 33mMDW-KOA
11/11Fri
2 stopsDelta
14h 35mKOA-MDW
$970
8/26Fri
2 stopsDelta
15h 38mMDW-KOA
8/29Mon
2 stopsDelta
16h 17mKOA-MDW
$988

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Recent one-way flight deals

10/26Wed
2 stopsDelta
28h 36mMDW-KOA
11/4Fri
2 stopsDelta
17h 57mKOA-MDW
$609
12/5Mon
2 stopsDelta
27h 33mMDW-KOA
12/13Tue
2 stopsDelta
21h 59mKOA-MDW
$623
10/30Sun
2 stopsDelta
28h 36mMDW-KOA
11/8Tue
2 stopsDelta
16h 26mKOA-MDW
$640
10/25Tue
2 stopsDelta
28h 36mMDW-KOA
11/2Wed
2 stopsDelta
16h 59mKOA-MDW
$647
11/1Tue
2 stopsDelta
30h 18mMDW-KOA
11/9Wed
2 stopsDelta
18h 07mKOA-MDW
$667
11/8Tue
2 stopsDelta
14h 18mMDW-KOA
11/16Wed
2 stopsDelta
18h 07mKOA-MDW
$669
11/2Wed
2 stopsDelta
17h 33mMDW-KOA
11/9Wed
2 stopsDelta
18h 07mKOA-MDW
$721
11/29Tue
2 stopsDelta
27h 33mMDW-KOA
12/7Wed
2 stopsDelta
18h 07mKOA-MDW
$727
12/7Wed
2 stopsDelta
14h 17mMDW-KOA
12/14Wed
2 stopsDelta
13h 25mKOA-MDW
$751
11/7Mon
2 stopsDelta
28h 43mMDW-KOA
11/16Wed
2 stopsDelta
17h 20mKOA-MDW
$753
11/14Mon
2 stopsDelta
27h 48mMDW-KOA
11/23Wed
2 stopsDelta
21h 55mKOA-MDW
$757
12/11Sun
2 stopsDelta
28h 42mMDW-KOA
12/20Tue
2 stopsDelta
21h 23mKOA-MDW
$809
7/11Mon
3 stopsMultiple Airlines
29h 24mMDW-KOA
7/15Fri
2 stopsMultiple Airlines
22h 20mKOA-MDW
$838
8/30Tue
2 stopsDelta
16h 32mMDW-KOA
9/7Wed
2 stopsDelta
14h 32mKOA-MDW
$858
8/24Wed
2 stopsDelta
14h 13mMDW-KOA
8/29Mon
2 stopsDelta
16h 17mKOA-MDW
$880
10/26Wed
2 stopsDelta
14h 11mMDW-KOA
11/2Wed
2 stopsDelta
16h 01mKOA-MDW
$909
10/29Sat
2 stopsDelta
14h 11mMDW-KOA
11/5Sat
2 stopsDelta
16h 26mKOA-MDW
$946
12/5Mon
2 stopsDelta
14h 17mMDW-KOA
12/12Mon
2 stopsDelta
15h 03mKOA-MDW
$964
11/4Fri
2 stopsDelta
17h 33mMDW-KOA
11/11Fri
2 stopsDelta
14h 35mKOA-MDW
$970
8/26Fri
2 stopsDelta
15h 38mMDW-KOA
8/29Mon
2 stopsDelta
16h 17mKOA-MDW
$988

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Chicago Midway Airport - Kailua-Kona Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Kailua-Kona (KOA)United States

Return flight deals:

Kailua-Kona - Chicago Midway Airport

Cabin classes:

$1,993