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Find cheap flights from Chicago Midway Airport to The Big Island from $315

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to The Big Island departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

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Best The Big Island Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Kailua-Kona
Kailua-Kona2 stops$690

Good to know

Cheapest flight

$315
Flight from Chicago Midway Airport to Kailua-Kona

FAQs - booking The Big Island flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to The Big Island?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to The Big Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to The Big Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to The Big Island from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to The Big Island?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to The Big Island with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to The Big Island?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to The Big Island from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Midway to The Big Island

 
Need help choosing which airline to fly with from Midway to The Big Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10848 reviews
8.2Boarding
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

8.0 ExcellentAnonymous, May 2024ATL - ATW
Read more about Delta reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

Book cheap flights from Chicago to The Big Island

Recent round-trip flight deals

5/15Wed
2 stopsDelta
17h 35mMDW-KOA
5/21Tue
2 stopsDelta
15h 27mKOA-MDW
$690
5/31Fri
2 stopsDelta
13h 49mMDW-KOA
6/7Fri
2 stopsDelta
19h 12mKOA-MDW
$782
5/21Tue
2 stopsDelta
14h 03mMDW-KOA
5/27Mon
2 stopsDelta
16h 25mKOA-MDW
$802
8/6Tue
2 stopsDelta
13h 56mMDW-KOA
8/14Wed
2 stopsDelta
16h 21mKOA-MDW
$855
5/17Fri
2 stopsDelta
14h 03mMDW-KOA
5/24Fri
2 stopsDelta
14h 15mKOA-MDW
$888
8/6Tue
2 stopsDelta
13h 56mMDW-KOA
8/14Wed
2 stopsDelta
16h 21mKOA-MDW
$889
10/8Tue
2 stopsDelta
13h 59mMDW-KOA
10/30Wed
2 stopsDelta
16h 20mKOA-MDW
$891
8/15Thu
2 stopsDelta
15h 17mMDW-KOA
8/19Mon
2 stopsDelta
16h 21mKOA-MDW
$898
6/2Sun
2 stopsDelta
14h 03mMDW-KOA
6/9Sun
2 stopsDelta
15h 31mKOA-MDW
$912
5/15Wed
2 stopsDelta
17h 30mMDW-KOA
5/20Mon
2 stopsDelta
16h 25mKOA-MDW
$950

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Recent one-way flight deals

6/5Wed
2 stopsDelta
14h 03mMDW-KOA
$315
8/10Sat
2 stopsDelta
13h 56mMDW-KOA
$396
5/31Fri
2 stopsDelta
13h 49mMDW-KOA
$538
7/27Sat
2 stopsDelta
16h 34mMDW-KOA
$539
5/9Thu
2 stopsDelta
13h 49mMDW-KOA
$546
6/20Thu
2 stopsDelta
14h 01mMDW-KOA
$606
6/2Sun
2 stopsDelta
13h 37mMDW-ITO
$696
6/22Sat
2 stopsDelta
15h 16mMDW-ITO
$866
6/19Wed
2 stopsDelta
13h 56mMDW-KOA
$892
6/21Fri
2 stopsDelta
15h 10mMDW-ITO
$1,126

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Last minute flights from Midway to The Big Island

Last minute flight, train and bus deals

5/7Tue
multi-stopDelta
13h 49mMDW-KOA
5/8Wed
multi-stopDelta
15h 24mKOA-MDW
$812
5/7Tue
multi-stopDelta
13h 49mMDW-KOA
5/8Wed
multi-stopDelta
16h 02mKOA-MDW
$813
5/9Thu
multi-stopDelta
13h 49mMDW-KOA
5/20Mon
multi-stopDelta
16h 25mKOA-MDW
$1,107
5/9Thu
multi-stopDelta
13h 49mMDW-KOA
5/18Sat
multi-stopDelta
16h 25mKOA-MDW
$1,138

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Chicago Midway Airport - The Big Island Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

The Big Island - Chicago Midway Airport

Cabin classes:

$527
$546
$292
$27