$327 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 10/25. 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

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

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

Thu, Oct 30 - Thu, Nov 20
Southwest Logo
7:45 am - 4:30 pmMDW-OGG
13h 45m1 stop
Southwest Logo
9:35 pm - 1:05 pmOGG-MDW
11h 30m1 stop
$447Southwest
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Thu, Oct 30 - Thu, Nov 20
Southwest Logo
7:45 am - 4:30 pmMDW-OGG
13h 45m1 stop
Southwest Logo
9:35 pm - 4:20 pmOGG-MDW
14h 45m2 stops
$452Southwest
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Wed, Dec 10 - Mon, Dec 15
Delta Logo
6:00 am - 8:18 pmMDW-OGG
18h 18m2 stops
Delta Logo
5:10 pm - 9:54 amOGG-MDW
12h 44m1 stop
$458Delta
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Tue, Nov 11 - Tue, Nov 18
Delta Logo
6:00 am - 6:56 pmMDW-OGG
16h 56m2 stops
Delta Logo
10:20 pm - 6:18 pmOGG-MDW
15h 58m2 stops
$463Delta
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Thu, Dec 4 - Sat, Dec 13
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
5:10 pm - 9:54 amOGG-MDW
12h 44m1 stop
$477Delta
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Thu, Jan 29 - Thu, Feb 5
Delta Logo
6:00 am - 3:30 pmMDW-OGG
13h 30m1 stop
Delta Logo
1:55 pm - 8:54 amOGG-MDW
14h 59m2 stops
$480Delta
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Thu, Feb 5 - Wed, Feb 11
Southwest Logo
5:10 am - 1:30 pmMDW-OGG
12h 20m1 stop
Southwest Logo
9:25 pm - 11:50 amOGG-MDW
10h 25m1 stop
$481Southwest
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Thu, Dec 4 - Sat, Dec 13
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
5:10 pm - 12:34 pmOGG-MDW
15h 24m2 stops
$482Delta
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Wed, Jan 21 - Fri, Jan 30
Delta Logo
9:30 am - 7:15 pmMDW-OGG
13h 45m2 stops
Delta Logo
5:00 pm - 9:56 amOGG-MDW
12h 56m1 stop
$484Delta
Find Deal
Thu, Feb 5 - Wed, Feb 11
Southwest Logo
5:10 am - 1:30 pmMDW-OGG
12h 20m1 stop
Southwest Logo
7:00 pm - 12:15 pmOGG-MDW
13h 15m2 stops
$486Southwest
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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 $333, prices are generally cheapest when you fly direct.

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Good to know

Low seasonAugust
Cheapest flight$357
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 16% 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 4237 reviews
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

mandatory demand customer to check their carry on because not enough people check bags.

6.0 GoodHung, Oct 2025PHX - ABQ
Read more Southwest reviews

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

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.

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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