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Find cheap flights from Chicago Midway Airport to The Big Island from $333

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
Sat 6/15
Sat 6/22

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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$432
Hilo
Hilo2 stops$1,399

Good to know

Cheapest flight

$333
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 10673 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

Book cheap flights from Chicago to The Big Island

Recent round-trip flight deals

8/16Fri
2 stopsDelta
13h 50mMDW-KOA
8/20Tue
2 stopsDelta
15h 18mKOA-MDW
$432
9/6Fri
2 stopsDelta
13h 50mMDW-KOA
9/11Wed
2 stopsDelta
15h 06mKOA-MDW
$572
8/15Thu
2 stopsDelta
17h 25mMDW-KOA
8/22Thu
2 stopsDelta
15h 18mKOA-MDW
$611
7/25Thu
2 stopsDelta
14h 00mMDW-KOA
8/5Mon
2 stopsDelta
15h 18mKOA-MDW
$752
8/6Tue
2 stopsDelta
17h 25mMDW-KOA
8/14Wed
2 stopsDelta
16h 21mKOA-MDW
$793
5/28Tue
2 stopsDelta
13h 49mMDW-KOA
6/1Sat
2 stopsDelta
15h 24mKOA-MDW
$855
7/18Thu
2 stopsDelta
14h 00mMDW-KOA
7/29Mon
2 stopsDelta
15h 23mKOA-MDW
$912
7/26Fri
2 stopsDelta
17h 33mMDW-KOA
8/2Fri
2 stopsDelta
15h 23mKOA-MDW
$930
6/25Tue
2 stopsDelta
16h 20mMDW-KOA
7/3Wed
2 stopsDelta
19h 13mKOA-MDW
$988
7/26Fri
2 stopsDelta
16h 21mMDW-KOA
8/4Sun
2 stopsDelta
15h 22mKOA-MDW
$995

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Recent one-way flight deals

6/5Wed
2 stopsDelta
17h 35mMDW-KOA
$333
6/5Wed
2 stopsDelta
14h 03mMDW-KOA
$356
8/31Sat
2 stopsDelta
13h 34mMDW-ITO
$419
6/19Wed
2 stopsDelta
16h 20mMDW-KOA
$479

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Last minute flights from Midway to The Big Island

Last minute flight, train and bus deals

5/19Sun
multi-stopDelta
13h 49mMDW-KOA
5/29Wed
multi-stopDelta
15h 27mKOA-MDW
$562
5/20Mon
multi-stopDelta
13h 49mMDW-KOA
5/29Wed
multi-stopDelta
15h 27mKOA-MDW
$612
5/18Sat
multi-stopDelta
14h 03mMDW-KOA
5/25Sat
multi-stopDelta
15h 13mKOA-MDW
$646
5/19Sun
multi-stopDelta
13h 49mMDW-KOA
5/31Fri
multi-stopDelta
15h 13mKOA-MDW
$665
5/20Mon
multi-stopDelta
13h 49mMDW-KOA
5/31Fri
multi-stopDelta
15h 13mKOA-MDW
$715
5/21Tue
multi-stopDelta
16h 42mMDW-KOA
5/28Tue
multi-stopDelta
15h 24mKOA-MDW
$772

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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:

$636
$598
$477
$27