$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 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

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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Flights Deals

Best Maui Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Kahului
Kahului1 stop$550
Kahului
Kahului1 stop$550

Cheap Flights from Midway to Maui

 
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.

Recent round-trip flight deals from Midway to Maui

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Maui.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
6:10 am - 12:25 pmMDW-OGG
11h 15m1 stop
Southwest Logo
8:30 pm - 1:55 pmOGG-MDW
12h 25m1 stop
$550Southwest
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Tue, Sep 2 - Tue, Sep 9
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:30 pm - 1:55 pmOGG-MDW
12h 25m1 stop
$555Southwest
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:30 pm - 1:45 pmOGG-MDW
12h 15m2 stops
$560Southwest
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
5:10 am - 12:25 pmMDW-OGG
12h 15m1 stop
Southwest Logo
8:30 pm - 1:55 pmOGG-MDW
12h 25m1 stop
$580Southwest
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Thu, Aug 21 - Tue, Aug 26
Southwest Logo
5:10 am - 12:25 pmMDW-OGG
12h 15m1 stop
Southwest Logo
8:30 pm - 3:55 pmOGG-MDW
14h 25m2 stops
$585Southwest
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Thu, Aug 21 - Tue, Aug 26
Delta Logo
6:00 am - 7:33 pmMDW-OGG
18h 33m2 stops
Delta Logo
12:05 pm - 8:46 amOGG-MDW
15h 41m2 stops
$641Delta
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Sat, Aug 9 - Mon, Sep 8
Southwest Logo
5:35 am - 1:00 pmMDW-OGG
12h 25m1 stop
Southwest Logo
8:25 pm - 2:30 pmOGG-MDW
13h 05m1 stop
$644Southwest
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Thu, Aug 7 - Thu, Aug 14
Delta Logo
9:20 am - 7:25 pmMDW-OGG
15h 05m2 stops
Delta Logo
12:00 pm - 8:40 amOGG-MDW
15h 40m2 stops
$648Delta
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Sat, May 24 - Thu, May 29
Southwest Logo
5:10 am - 12:25 pmMDW-OGG
12h 15m1 stop
Southwest Logo
8:25 pm - 2:40 pmOGG-MDW
13h 15m2 stops
$649Southwest
Find Deal
Thu, Aug 7 - Thu, Aug 14
Southwest Logo
5:10 am - 12:25 pmMDW-OGG
12h 15m1 stop
Southwest Logo
10:05 am - 5:00 amOGG-MDW
13h 55m2 stops
$658Southwest
Find Deal
Mon, Sep 29 - Mon, Oct 6
Useful Info

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.

Which airlines provide the cheapest flights from Chicago Midway Airport to Maui?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Maui were found on Southwest ($550) and Delta ($641).

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Good to know

Low seasonAugust
High seasonFebruary
Cheapest flight$327
Best time to beat the crowds with an average 30% 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.

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 4293 reviews
7.1Food
8.0Comfort
8.6Crew
8.2Boarding
7.6Entertainment
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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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