MDW

$224 Find Cheap Flights from Hawaii to Chicago Midway Airport

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 11/24. 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

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Flight Deals

Cheap Flights from Hawaii to Midway

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

Mon, Nov 17 - Mon, Jan 12
Delta Logo
4:45 pm - 8:52 amHNL-MDW
12h 07m1 stop
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
$475Delta
Find Deal
Mon, Nov 17 - Mon, Jan 12
Delta Logo
4:45 pm - 1:07 pmHNL-MDW
16h 22m2 stops
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
$480Delta
Find Deal
Mon, Nov 17 - Mon, Jan 12
Delta Logo
4:45 pm - 11:52 amHNL-MDW
15h 07m2 stops
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
$486Delta
Find Deal
Mon, Nov 17 - Mon, Jan 5
Delta Logo
4:45 pm - 8:52 amHNL-MDW
12h 07m1 stop
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
$511Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
2:50 pm - 8:40 amHNL-MDW
12h 50m1 stop
Delta Logo
9:35 am - 8:26 pmMDW-HNL
15h 51m2 stops
$516Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
1:20 pm - 8:55 amHNL-MDW
14h 35m2 stops
Delta Logo
9:35 am - 8:26 pmMDW-HNL
15h 51m2 stops
$522Delta
Find Deal
Mon, Oct 27 - Mon, Nov 3
Southwest Logo
9:05 pm - 3:15 pmHNL-MDW
13h 10m2 stops
Southwest Logo
8:20 am - 9:00 pmMDW-HNL
16h 40m1 stop
$539Southwest
Find Deal
Tue, Feb 24 - Fri, Feb 27
Southwest Logo
9:25 pm - 12:35 pmKOA-MDW
11h 10m1 stop
Southwest Logo
5:00 am - 1:45 pmMDW-KOA
12h 45m1 stop
$579Southwest
Find Deal
Tue, Feb 24 - Fri, Feb 27
Southwest Logo
7:00 pm - 12:35 pmKOA-MDW
13h 35m2 stops
Southwest Logo
5:00 am - 1:45 pmMDW-KOA
12h 45m1 stop
$584Southwest
Find Deal
Mon, Oct 13 - Mon, Oct 20
Multiple Airlines Logo
3:01 pm - 11:25 pmHNL-MDW
27h 24m1 stop
Multiple Airlines Logo
5:28 pm - 11:10 amMDW-HNL
46h 42m2 stops
$669Multiple Airlines
Find Deal

Everything you should know

Cheapest round-trip
$475
Delta
Mon 11/17Mon 1/12
HNL - MDW • 1 stop
Cheapest one-way
$224
Southwest
Mon 11/24
KOA - MDW • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$224
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Kailua-Kona to Chicago Midway Airport

FAQs for booking Hawaii to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Hawaii 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 Hawaii to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii 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 Hawaii 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 Hawaii 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 Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii 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 Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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