$290 Find Cheap Flights from Chicago Midway Airport to The Big Island

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 3/16. 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$462
Hilo
Hilo2 stops$631
Kailua-Kona
Kailua-Kona2 stops$462
Hilo
Hilo2 stops$631

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

Tue, Feb 24 - Tue, Mar 3
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
10:55 pm - 6:40 pm
KOA
-
MDW
15h 45m
2 stops
$462Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
10:15 pm - 5:54 pm
KOA
-
MDW
14h 39m
2 stops
$465Delta
Wed, Mar 4 - Wed, Mar 18
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$481Southwest
Wed, Mar 4 - Wed, Mar 18
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$501Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
7:05 am - 12:10 am
KOA
-
MDW
13h 05m
2 stops
$514Southwest
Mon, Feb 23 - Mon, Mar 2
Delta Logo
7:20 pm - 6:30 pm
MDW
-
KOA
27h 10m
2 stops
Delta Logo
10:55 pm - 5:37 pm
KOA
-
MDW
14h 42m
2 stops
$529Delta
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
9:25 pm - 2:45 pm
KOA
-
MDW
13h 20m
2 stops
$530Southwest
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
9:25 pm - 12:35 pm
KOA
-
MDW
11h 10m
1 stop
$546Southwest
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
10:00 am - 9:25 pm
MDW
-
KOA
16h 25m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$552Southwest
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
5:05 am - 2:45 pm
MDW
-
KOA
13h 40m
2 stops
Southwest Logo
8:25 pm - 2:50 pm
KOA
-
MDW
13h 25m
1 stop
$557Southwest
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 $376, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$290
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 4267 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

10.0 ExcellentJoseph, Jan 2026
BWI - RIC
Read more Southwest reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)