$452 Find Cheap Flights from Chicago Midway Airport to The Big Island

This is the cheapest round-trip 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 4/20. 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
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to The Big Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to The Big Island, as well as popular online travel agencies
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Cheap Flights from Midway to The Big Island

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kailua-Kona
Kailua-Kona2 stops$452
Hilo
Hilo2 stops$930
Kailua-Kona
Kailua-Kona2 stops$452
Hilo
Hilo2 stops$930

Book Cheap Midway to The Big Island Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to The Big Island that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to The Big Island

Mon, Apr 20 - Mon, Apr 27
Southwest Logo
5:10 am - 2:30 pm
MDW
-
KOA
14h 20m
2 stops
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$452Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
5:10 am - 2:30 pm
MDW
-
KOA
14h 20m
2 stops
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$457Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
10:20 am - 9:25 pm
MDW
-
KOA
16h 05m
2 stops
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$484Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
10:20 am - 9:25 pm
MDW
-
KOA
16h 05m
2 stops
Southwest Logo
7:00 pm - 12:00 pm
KOA
-
MDW
12h 00m
2 stops
$489Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$498Southwest
Mon, Apr 13 - Mon, Apr 20
Southwest Logo
5:10 am - 1:15 pm
MDW
-
KOA
13h 05m
1 stop
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$501Southwest
Mon, Apr 13 - Mon, Apr 20
Southwest Logo
5:10 am - 2:30 pm
MDW
-
KOA
14h 20m
2 stops
Southwest Logo
8:25 pm - 12:00 pm
KOA
-
MDW
10h 35m
1 stop
$508Southwest
Fri, Apr 17 - Thu, Apr 23
Southwest Logo
5:10 am - 1:15 pm
MDW
-
KOA
13h 05m
1 stop
Southwest Logo
8:25 pm - 2:20 pm
KOA
-
MDW
12h 55m
2 stops
$511Southwest
Thu, Mar 26 - Wed, Apr 1
Delta Logo
6:00 am - 5:27 pm
MDW
-
ITO
16h 27m
2 stops
Delta Logo
12:21 pm - 8:50 am
ITO
-
MDW
15h 29m
2 stops
$1,295Delta
Thu, Mar 26 - Tue, Mar 31
Delta Logo
6:00 am - 4:15 pm
MDW
-
ITO
15h 15m
2 stops
Delta Logo
1:46 pm - 8:50 am
ITO
-
MDW
14h 04m
2 stops
$1,328Delta
Booking Insights

KAYAK's insights & trends for Midway to The Big Island flights

Get data-powered insights and trends into flights from Midway to The Big Island to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago Midway Airport to The Big Island?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $381, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$452
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 from Chicago Midway Airport to The Big Island 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 from Chicago Midway Airport to The Big Island with an airline and back 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 from Chicago Midway Airport to The Big Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to The Big Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to The Big Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4324 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Everything you need to know for your flight to The Big Island

Information on your arrival and departure airports

Chicago Midway Airport (MDW)