$257 Find Cheap Flights from Chicago Midway Airport to Maui - 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 Maui departing on 9/1. 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

Book Cheap Midway to Maui 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 Maui 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 Maui

Wed, Dec 9 - Wed, Jan 20
Southwest Logo
5:45 am - 1:10 pm
MDW
-
OGG
11h 25m
1 stop
Southwest Logo
9:25 pm - 12:35 pm
OGG
-
MDW
11h 10m
1 stop
$554Southwest
Sun, Nov 1 - Thu, Nov 12
Southwest Logo
5:45 am - 4:10 pm
MDW
-
OGG
14h 25m
2 stops
Southwest Logo
9:25 pm - 1:30 pm
OGG
-
MDW
12h 05m
1 stop
$560Southwest
Wed, Oct 21 - Tue, Nov 3
Southwest Logo
10:15 am - 6:15 pm
MDW
-
OGG
13h 00m
2 stops
Southwest Logo
9:25 pm - 12:05 pm
OGG
-
MDW
10h 40m
1 stop
$560Southwest
Tue, Jan 26 - Tue, Feb 2
Southwest Logo
10:00 am - 9:15 pm
MDW
-
OGG
15h 15m
2 stops
Southwest Logo
8:15 pm - 11:20 am
OGG
-
MDW
11h 05m
1 stop
$560Southwest
Tue, Nov 17 - Tue, Nov 24
Southwest Logo
5:45 am - 4:40 pm
MDW
-
OGG
14h 55m
2 stops
Southwest Logo
9:25 pm - 4:35 pm
OGG
-
MDW
15h 10m
1 stop
$560Southwest
Tue, Sep 22 - Wed, Sep 30
Southwest Logo
6:50 am - 4:10 pm
MDW
-
OGG
14h 20m
2 stops
Southwest Logo
8:55 pm - 12:10 pm
OGG
-
MDW
10h 15m
1 stop
$560Southwest
Wed, Oct 28 - Tue, Nov 10
Southwest Logo
10:15 am - 6:15 pm
MDW
-
OGG
13h 00m
2 stops
Southwest Logo
11:20 pm - 5:20 pm
OGG
-
MDW
14h 00m
1 stop
$560Southwest
Wed, Dec 9 - Wed, Jan 20
Southwest Logo
5:25 am - 2:40 pm
MDW
-
OGG
13h 15m
2 stops
Southwest Logo
8:15 pm - 11:20 am
OGG
-
MDW
11h 05m
1 stop
$560Southwest
Sun, Jan 24 - Fri, Feb 5
Delta Logo
6:00 am - 2:52 pm
MDW
-
OGG
12h 52m
1 stop
Delta Logo
5:10 pm - 8:49 am
OGG
-
MDW
11h 39m
1 stop
$574Delta
Tue, Jan 26 - Wed, Feb 3
Delta Logo
6:00 am - 2:52 pm
MDW
-
OGG
12h 52m
1 stop
Delta Logo
4:35 pm - 9:52 am
OGG
-
MDW
13h 17m
1 stop
$574Delta
Booking Insights

KAYAK's insights & trends for Midway to Maui flights

Get data-powered insights and trends into flights from Midway to Maui 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 Maui?

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 $411, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight

$257
Flight from Chicago Midway Airport to Kahului

FAQs - booking Maui flights

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

    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 Maui.

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

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

    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 Maui 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 Maui?

    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 Maui 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 Maui

Information on your arrival and departure airports

Chicago Midway Airport (MDW)