$231 Find Cheap Flights from Chicago Midway Airport to Maui

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 11/18. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Maui

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Maui

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kahului
Kahului1 stop$491
Kahului
Kahului1 stop$491

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, Oct 22 - Wed, Oct 29
Southwest Logo
6:05 am - 12:25 pmMDW-OGG
11h 20m1 stop
Southwest Logo
8:30 pm - 1:20 pmOGG-MDW
11h 50m1 stop
$491Southwest
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Thu, Oct 30 - Tue, Nov 4
Southwest Logo
7:45 am - 4:30 pmMDW-OGG
13h 45m1 stop
Southwest Logo
9:35 pm - 3:00 pmOGG-MDW
13h 25m2 stops
$497Southwest
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Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:15 am - 1:10 pmMDW-OGG
11h 55m1 stop
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$506Southwest
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Wed, Oct 22 - Wed, Oct 29
Southwest Logo
7:40 am - 4:30 pmMDW-OGG
13h 50m2 stops
Southwest Logo
8:30 pm - 1:20 pmOGG-MDW
11h 50m1 stop
$511Southwest
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Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:15 am - 2:50 pmMDW-OGG
13h 35m2 stops
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$513Southwest
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Wed, Oct 22 - Tue, Oct 28
Southwest Logo
6:25 am - 12:50 pmMDW-OGG
11h 25m1 stop
Southwest Logo
8:30 pm - 12:25 pmOGG-MDW
10h 55m1 stop
$521Southwest
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Tue, Oct 28 - Tue, Nov 4
Southwest Logo
7:40 am - 4:30 pmMDW-OGG
13h 50m2 stops
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$527Southwest
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Wed, Dec 3 - Wed, Dec 10
Delta Logo
6:00 am - 7:27 pmMDW-OGG
17h 27m2 stops
Delta Logo
1:45 pm - 8:46 amOGG-MDW
15h 01m2 stops
$532Delta
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Tue, Sep 23 - Mon, Sep 29
Southwest Logo
6:40 am - 1:00 pmMDW-OGG
11h 20m1 stop
Southwest Logo
8:30 pm - 12:15 pmOGG-MDW
10h 45m1 stop
$537Southwest
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Tue, Nov 11 - Mon, Nov 17
Delta Logo
6:00 am - 7:21 pmMDW-OGG
17h 21m2 stops
Delta Logo
10:20 pm - 6:18 pmOGG-MDW
15h 58m2 stops
$624Delta
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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 $318, prices are generally cheapest when you fly direct.

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

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 Maui, 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 Maui is August, when tickets cost $630 (return) on average. On the other hand, the most expensive months are November and May, when the average cost of round-trip tickets is $1,673 and $1,138 respectively.

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Good to know

Low seasonSeptember
Cheapest flight$231
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 12% lower on average.
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.

  • What is the cheapest time of day to fly to Maui?

    The cheapest time of day to fly to Maui is generally in the morning, when round-trip flights cost $741 on average. The most expensive time of day to fly to Maui is generally in the morning, which is peak travel time and where the average cost of a ticket is $741.

Reviews of the top airline flying from Midway to Maui

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maui. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Maui? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

6.0 GoodCarl, Aug 2025MSY - BWI
Read more Southwest reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Everything you need to know for your flight to Maui

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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