$227 Find Cheap Flights from Chicago Midway Airport to Hawaii - 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 Hawaii departing on 8/25. 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 Hawaii

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Honolulu
Honolulu1 stop$620
Kahului
Kahului2 stops$560
Kailua-Kona
Kailua-Kona1 stop$454
Lihue
Lihue2 stops$435
Hilo
Hilo1 stop$494
Honolulu
Honolulu1 stop$620
Kahului
Kahului2 stops$560
Kailua-Kona
Kailua-Kona1 stop$454
Lihue
Lihue2 stops$435
Hilo
Hilo1 stop$494

Book Cheap Midway to Hawaii 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 Hawaii 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 Hawaii

Wed, Oct 28 - Sun, Nov 1
Delta Logo
9:29 am - 7:14 pm
MDW
-
LIH
14h 45m
2 stops
Delta Logo
9:47 pm - 4:47 pm
LIH
-
MDW
15h 00m
2 stops
$435Delta
Sat, Nov 14 - Tue, Nov 24
Delta Logo
9:30 am - 8:13 pm
MDW
-
LIH
14h 43m
2 stops
Delta Logo
9:40 pm - 4:39 pm
LIH
-
MDW
14h 59m
2 stops
$443Delta
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
8:35 pm - 12:05 pm
KOA
-
MDW
10h 30m
1 stop
$454Southwest
Wed, Oct 28 - Sun, Nov 1
Delta Logo
9:29 am - 7:14 pm
MDW
-
LIH
14h 45m
2 stops
Delta Logo
9:47 pm - 4:47 pm
LIH
-
MDW
15h 00m
2 stops
$455Delta
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
8:35 pm - 3:15 pm
KOA
-
MDW
13h 40m
2 stops
$460Southwest
Wed, Oct 28 - Sun, Nov 1
Delta Logo
9:29 am - 7:14 pm
MDW
-
LIH
14h 45m
2 stops
Delta Logo
9:47 pm - 4:47 pm
LIH
-
MDW
15h 00m
2 stops
$463Delta
Tue, Oct 20 - Tue, Nov 3
Delta Logo
9:29 am - 7:19 pm
MDW
-
LIH
14h 50m
2 stops
Delta Logo
10:51 pm - 4:47 pm
LIH
-
MDW
13h 56m
2 stops
$485Delta
Fri, Dec 4 - Sat, Dec 12
Delta Logo
9:30 am - 8:13 pm
MDW
-
LIH
14h 43m
2 stops
Delta Logo
9:40 pm - 6:04 pm
LIH
-
MDW
16h 24m
2 stops
$485Delta
Wed, Oct 28 - Sun, Nov 1
Delta Logo
9:29 am - 7:14 pm
MDW
-
LIH
14h 45m
2 stops
Delta Logo
9:47 pm - 4:47 pm
LIH
-
MDW
15h 00m
2 stops
$485Delta
Sat, Nov 7 - Wed, Nov 11
Delta Logo
9:29 am - 8:14 pm
MDW
-
LIH
14h 45m
2 stops
Delta Logo
9:40 pm - 4:39 pm
LIH
-
MDW
14h 59m
2 stops
$492Delta
Booking Insights

KAYAK's insights & trends for Midway to Hawaii flights

Get data-powered insights and trends into flights from Midway to Hawaii to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago Midway Airport to Hawaii?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Hawaii departing in September.

Flight prices are below average for this route right now.

Flights to Hawaii from Chicago Midway Airport usually cost between $621 and $728 in September.
The lowest price found in the past 5 days was $620 on Southwest (Sep 1-Sep 10).

What is the cheapest month to fly from Chicago Midway Airport to Hawaii?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Hawaii, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Hawaii is January, when tickets cost $429 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,011 and $909 respectively.

Find deals

Good to know

Low season

September

Cheapest flight

$227
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway Airport to Honolulu

FAQs - booking Hawaii flights

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

    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 Hawaii.

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

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

    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 Hawaii 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 Hawaii?

    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 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 from Midway to Hawaii

Information on your arrival and departure airports

Chicago Midway Airport (MDW)