MDW

$205 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 9/10. 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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Flights 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, Nov 6 - Sun, Nov 9
Southwest Logo
8:00 am - 1:30 amHNL-MDW
13h 30m1 stop
Southwest Logo
7:45 am - 4:15 pmMDW-HNL
12h 30m1 stop
$409Southwest
Find Deal
Thu, Nov 6 - Sun, Nov 9
Southwest Logo
9:25 pm - 4:20 pmHNL-MDW
14h 55m2 stops
Southwest Logo
7:45 am - 4:15 pmMDW-HNL
12h 30m1 stop
$414Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
8:05 am - 12:35 amHNL-MDW
11h 30m1 stop
Southwest Logo
9:25 pm - 10:20 amMDW-HNL
17h 55m1 stop
$442Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
8:05 am - 12:35 amHNL-MDW
11h 30m1 stop
Southwest Logo
5:05 am - 12:50 pmMDW-HNL
12h 45m2 stops
$459Southwest
Find Deal
Thu, Nov 6 - Sun, Nov 9
Southwest Logo
9:25 pm - 4:20 pmHNL-MDW
14h 55m2 stops
Southwest Logo
5:25 am - 4:15 pmMDW-HNL
14h 50m2 stops
$492Southwest
Find Deal
Fri, Aug 29 - Fri, Sep 5
Southwest Logo
11:35 am - 5:10 amHNL-MDW
12h 35m2 stops
Southwest Logo
12:10 pm - 9:00 pmMDW-HNL
13h 50m1 stop
$498Southwest
Find Deal
Mon, Sep 8 - Wed, Sep 24
Delta Logo
10:06 pm - 6:37 pmHNL-MDW
15h 31m2 stops
Delta Logo
9:20 am - 8:30 pmMDW-HNL
16h 10m2 stops
$504Delta
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
8:15 am - 5:00 amHNL-MDW
15h 45m2 stops
Southwest Logo
5:05 am - 12:50 pmMDW-HNL
12h 45m2 stops
$510Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
8:05 am - 12:35 amHNL-MDW
11h 30m1 stop
Southwest Logo
11:00 am - 9:00 pmMDW-HNL
15h 00m1 stop
$514Southwest
Find Deal
Wed, Sep 3 - Sun, Sep 7
Delta Logo
4:09 pm - 12:28 pmHNL-MDW
15h 19m2 stops
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
$538Delta
Find Deal
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Good to know

Low seasonJanuary
Cheapest flight$205
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 7% increase in price.
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.

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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