Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago Midway Airport to The Big Island from $266

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 9/7. 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
Tue 6/18
Tue 6/25

Search hundreds of travel sites at once for deals on flights to The Big Island

In the last 7 days travelers have searched 41,904,688 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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$447

Good to know

Cheapest flight

$266
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 10647 reviews
8.2Boarding
8.0Entertainment
7.4Food
8.6Crew
7.9Comfort
Airline reviews

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

2.0 MediocreRick, May 2024HNL - LAX
Read more about Delta reviews

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

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!

Book cheap flights from Chicago to The Big Island

Recent round-trip flight deals

8/29Thu
2 stopsDelta
13h 50mMDW-KOA
9/3Tue
2 stopsDelta
15h 18mKOA-MDW
$447
9/18Wed
2 stopsDelta
13h 59mMDW-KOA
9/27Fri
2 stopsDelta
16h 20mKOA-MDW
$469
8/30Fri
2 stopsDelta
13h 50mMDW-KOA
9/6Fri
2 stopsDelta
16h 21mKOA-MDW
$487
9/7Sat
2 stopsDelta
13h 50mMDW-KOA
9/13Fri
2 stopsDelta
16h 20mKOA-MDW
$497
9/5Thu
2 stopsDelta
13h 50mMDW-KOA
9/13Fri
2 stopsDelta
16h 20mKOA-MDW
$527
9/7Sat
2 stopsDelta
13h 50mMDW-KOA
9/16Mon
2 stopsDelta
16h 20mKOA-MDW
$532
9/6Fri
2 stopsDelta
13h 50mMDW-KOA
9/13Fri
2 stopsDelta
16h 20mKOA-MDW
$557
9/5Thu
2 stopsDelta
13h 50mMDW-KOA
9/16Mon
2 stopsDelta
16h 20mKOA-MDW
$562
9/7Sat
2 stopsDelta
13h 50mMDW-KOA
9/17Tue
2 stopsDelta
16h 20mKOA-MDW
$563
8/9Fri
2 stopsDelta
13h 50mMDW-KOA
8/23Fri
2 stopsDelta
15h 18mKOA-MDW
$592

Search by stops

Search by airline

Search by price

Recent one-way flight deals

9/7Sat
2 stopsDelta
13h 50mMDW-KOA
$266
8/31Sat
2 stopsDelta
13h 50mMDW-KOA
$291
8/31Sat
2 stopsDelta
13h 50mMDW-KOA
$296
9/10Tue
2 stopsDelta
27h 37mMDW-KOA
$304
9/6Fri
2 stopsDelta
29h 26mMDW-KOA
$314
9/8Sun
2 stopsDelta
17h 25mMDW-KOA
$375
6/5Wed
2 stopsDelta
14h 03mMDW-KOA
$396
6/19Wed
2 stopsDelta
16h 20mMDW-KOA
$539
8/5Mon
2 stopsDelta
17h 25mMDW-KOA
$669
8/5Mon
2 stopsDelta
17h 09mMDW-ITO
$793

Search by stops

Search by airline

Search by price

Last minute flights from Midway to The Big Island

Last minute flight, train and bus deals

5/24Fri
multi-stopDelta
14h 03mMDW-KOA
5/31Fri
multi-stopDelta
15h 13mKOA-MDW
$892
5/20Mon
multi-stopDelta
14h 03mMDW-KOA
5/27Mon
multi-stopDelta
14h 32mKOA-MDW
$912

Search by stops

Search by airline

Search by price

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