MDW

$292 Find Cheap Flights from The Big Island to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 8/28. 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

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Flight Deals

Cheap Flights from The Big Island to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from The Big Island to Midway 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 The Big Island to Midway

Thu, Oct 15 - Tue, Oct 20
Southwest Logo
10:00 am - 5:50 amKOA  Kona Intl-MDW Chicago Midway
14h 50m1 stop Sacramento Intl
Southwest Logo
10:15 am - 6:10 pmMDW  Chicago Midway-KOA Kona Intl
12h 55m2 stops San Jose Honolulu
$590Southwest
Thu, Oct 15 - Tue, Oct 20
Southwest Logo
11:40 am - 5:55 amKOA  Kona Intl-MDW Chicago Midway
13h 15m2 stops Honolulu Oakland
Southwest Logo
10:15 am - 6:10 pmMDW  Chicago Midway-KOA Kona Intl
12h 55m2 stops San Jose Honolulu
$595Southwest
Thu, Oct 15 - Wed, Oct 21
Southwest Logo
10:00 am - 5:50 amKOA  Kona Intl-MDW Chicago Midway
14h 50m1 stop Sacramento Intl
Southwest Logo
6:05 am - 12:35 pmMDW  Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
$614Southwest
Thu, Oct 15 - Wed, Oct 21
Southwest Logo
10:00 am - 5:50 amKOA  Kona Intl-MDW Chicago Midway
14h 50m1 stop Sacramento Intl
Southwest Logo
10:15 am - 9:30 pmMDW  Chicago Midway-KOA Kona Intl
16h 15m2 stops San Jose Honolulu
$620Southwest
Thu, Oct 15 - Wed, Oct 21
Southwest Logo
11:40 am - 5:55 amKOA  Kona Intl-MDW Chicago Midway
13h 15m2 stops Honolulu Oakland
Southwest Logo
10:15 am - 6:10 pmMDW  Chicago Midway-KOA Kona Intl
12h 55m2 stops San Jose Honolulu
$625Southwest
Fri, Oct 16 - Wed, Oct 21
Southwest Logo
11:40 am - 5:55 amKOA  Kona Intl-MDW Chicago Midway
13h 15m2 stops Honolulu Oakland
Southwest Logo
6:05 am - 12:35 pmMDW  Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
$675Southwest
Fri, Oct 16 - Wed, Oct 21
Southwest Logo
11:40 am - 5:55 amKOA  Kona Intl-MDW Chicago Midway
13h 15m2 stops Honolulu Oakland
Southwest Logo
10:15 am - 9:30 pmMDW  Chicago Midway-KOA Kona Intl
16h 15m2 stops San Jose Honolulu
$680Southwest
Wed, Sep 2 - Tue, Sep 8
Delta Logo
10:05 pm - 6:33 pmKOA  Kona Intl-MDW Chicago Midway
15h 28m2 stops Los Angeles Los Angeles Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 46m2 stops Detroit Metropolitan Wayne County Los Angeles Los Angeles
$735Delta
Fri, Oct 16 - Thu, Oct 22
Delta Logo
10:02 pm - 6:00 pmKOA  Kona Intl-MDW Chicago Midway
14h 58m2 stops Los Angeles Los Angeles Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 7:26 pmMDW  Chicago Midway-KOA Kona Intl
14h 57m2 stops Detroit Metropolitan Wayne County Los Angeles Los Angeles
$1,475Delta
Wed, Sep 9 - Sun, Sep 13
Delta Logo
10:10 pm - 10:44 pmKOA  Kona Intl-MDW Chicago Midway
19h 34m2 stops Los Angeles Los Angeles Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
18h 10m2 stops Atlanta Hartsfield-Jackson Los Angeles Los Angeles
$1,646Delta
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Good to know

Low season

January

Cheapest flight

$292
Most popular time to fly and prices are also 9% lower on average.
Flight from Kailua-Kona to Chicago Midway Airport

FAQs for booking The Big Island to Chicago Midway Airport flights

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

    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 The Big Island to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 The Big Island to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to The Big Island with another airline.

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

    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 Chicago Midway Airport from The Big Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)