$292 Find Cheap Flights from Chicago Midway Airport to The Big Island - 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 from Midway to The Big Island departing on 9/16. 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

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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-Kona1 stop$584
Hilo
Hilo1 stop$584
Kailua-Kona
Kailua-Kona1 stop$584
Hilo
Hilo1 stop$584

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, Nov 3 - Tue, Nov 10
Southwest Logo
5:50 am - 2:00 pmMDW  Chicago Midway-KOA Kona Intl
12h 10m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:30 pm - 2:10 pmKOA  Kona Intl-MDW Chicago Midway
12h 40m1 stop Las Vegas Harry Reid Intl
$584Southwest
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
6:50 am - 12:45 pmMDW  Chicago Midway-KOA Kona Intl
10h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
8:35 pm - 1:30 pmKOA  Kona Intl-MDW Chicago Midway
11h 55m1 stop Las Vegas Harry Reid Intl
$584Southwest
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
5:50 am - 2:00 pmMDW  Chicago Midway-KOA Kona Intl
12h 10m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:30 pm - 2:10 pmKOA  Kona Intl-MDW Chicago Midway
12h 40m1 stop Las Vegas Harry Reid Intl
$584Southwest
Mon, Nov 9 - Fri, Nov 13
Southwest Logo
5:45 am - 1:40 pmMDW  Chicago Midway-KOA Kona Intl
11h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:00 am - 5:45 amKOA  Kona Intl-MDW Chicago Midway
16h 45m1 stop Sacramento Intl
$584Southwest
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
6:40 am - 12:35 pmMDW  Chicago Midway-ITO Hilo Intl
10h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
8:45 pm - 12:05 pmITO  Hilo Intl-MDW Chicago Midway
10h 20m1 stop Las Vegas Harry Reid Intl
$584Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
6:50 am - 12:45 pmMDW  Chicago Midway-KOA Kona Intl
10h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
10:00 am - 5:45 amKOA  Kona Intl-MDW Chicago Midway
14h 45m1 stop Sacramento Intl
$589Southwest
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
6:40 am - 12:35 pmMDW  Chicago Midway-ITO Hilo Intl
10h 55m1 stop Las Vegas Harry Reid Intl
Southwest Logo
8:45 pm - 2:20 pmITO  Hilo Intl-MDW Chicago Midway
12h 35m2 stops Las Vegas Harry Reid Intl Dallas Love Field
$590Southwest
Sat, Nov 7 - Wed, Nov 11
Delta Logo
4:19 pm - 8:27 pmMDW  Chicago Midway-KOA Kona Intl
32h 08m2 stops Atlanta Hartsfield-Jackson Los Angeles
Delta Logo
9:40 pm - 10:56 pmKOA  Kona Intl-MDW Chicago Midway
21h 16m2 stops Los Angeles Atlanta Hartsfield-Jackson
$613Delta
Sat, Jan 23 - Tue, Jan 26
Delta Logo
5:35 pm - 6:39 pmMDW  Chicago Midway-KOA Kona Intl
29h 04m2 stops Minneapolis St Paul Los Angeles
Delta Logo
9:40 pm - 4:50 pmKOA  Kona Intl-MDW Chicago Midway
15h 10m2 stops Los Angeles Minneapolis St Paul
$635Delta
Sat, Jan 23 - Wed, Jan 27
Delta Logo
5:35 pm - 6:39 pmMDW  Chicago Midway-KOA Kona Intl
29h 04m2 stops Minneapolis St Paul Los Angeles
Delta Logo
9:40 pm - 4:50 pmKOA  Kona Intl-MDW Chicago Midway
15h 10m2 stops Los Angeles Minneapolis St Paul
$635Delta
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 $401, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight

$292
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.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)