$277 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 9/25. 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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Flights Deals

Best Maui Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kahului
Kahului2 stops$468
Kahului
Kahului2 stops$468

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.
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 - Tue, Nov 11
Southwest Logo
6:00 am - 2:40 pmMDW-OGG
13h 40m2 stops
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$468Southwest
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Thu, Nov 13 - Tue, Nov 18
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
10:10 pm - 6:07 pmOGG-MDW
15h 57m2 stops
$476Delta
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Wed, Oct 22 - Tue, Nov 11
Southwest Logo
6:25 am - 1:00 pmMDW-OGG
11h 35m1 stop
Southwest Logo
9:35 pm - 1:40 pmOGG-MDW
12h 05m1 stop
$481Southwest
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Wed, Sep 10 - Wed, Sep 17
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:25 pm - 2:30 pmOGG-MDW
13h 05m1 stop
$510Southwest
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Wed, Sep 10 - Wed, Sep 17
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:25 pm - 7:50 pmOGG-MDW
18h 25m2 stops
$516Southwest
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Tue, Aug 19 - Wed, Aug 27
Southwest Logo
6:10 am - 12:25 pmMDW-OGG
11h 15m1 stop
Southwest Logo
8:30 pm - 12:20 pmOGG-MDW
10h 50m1 stop
$543Southwest
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Tue, Aug 19 - Wed, Aug 27
Southwest Logo
6:10 am - 12:25 pmMDW-OGG
11h 15m1 stop
Southwest Logo
8:30 pm - 2:40 pmOGG-MDW
13h 10m2 stops
$548Southwest
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Mon, Sep 29 - Mon, Oct 6
Southwest Logo
5:15 am - 12:25 pmMDW-OGG
12h 10m1 stop
Southwest Logo
8:30 pm - 3:30 pmOGG-MDW
14h 00m1 stop
$559Southwest
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Mon, Sep 29 - Mon, Oct 6
Southwest Logo
5:15 am - 12:25 pmMDW-OGG
12h 10m1 stop
Southwest Logo
8:25 pm - 1:35 pmOGG-MDW
12h 10m2 stops
$564Southwest
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Fri, Oct 31 - Tue, Nov 4
Delta Logo
6:00 am - 6:23 pmMDW-OGG
17h 23m2 stops
Delta Logo
10:10 pm - 6:07 pmOGG-MDW
15h 57m2 stops
$593Delta
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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 $339, 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
High seasonFebruary
Cheapest flight$277
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 13% 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 4252 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.6Entertainment
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

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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