MDW

$221 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 5/7. 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 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

Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$362Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$368Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$438Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$444Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
8:55 pm - 2:20 pm
HNL
-
MDW
12h 25m
2 stops
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$464Southwest
Thu, Apr 16 - Wed, Apr 29
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
$480Delta
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
$485Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
11:45 am - 9:00 pm
MDW
-
HNL
14h 15m
2 stops
$491Southwest
Tue, May 5 - Mon, May 11
Southwest Logo
11:05 am - 5:45 am
HNL
-
MDW
13h 40m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$511Southwest
Mon, Apr 13 - Mon, Apr 20
Delta Logo
8:50 pm - 6:36 pm
KOA
-
MDW
16h 46m
2 stops
Delta Logo
6:00 am - 7:03 pm
MDW
-
KOA
18h 03m
2 stops
$573Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$221
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 2% 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
Lansing
Valparaiso
Chesterton
Schererville
Munster
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)