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Find cheap flights from Chicago Midway Airport to Maui from $416

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 7/10. 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
0 bags
Mon 7/1
Mon 7/8

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Best Maui Flight Deals

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

Kahului
Kahului2 stops$678

Good to know

Low season

August

High season

June

Cheapest flight

$416
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 62% increase in price.
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 to Maui from Chicago Midway Airport 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 to Maui with an airline and back to Chicago Midway Airport 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 to Maui from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Midway to Maui

 
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
DeltaOverall score based on 10419 reviews
7.9Comfort
8.6Crew
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Book cheap flights from Chicago to Maui

Recent round-trip flight deals

8/16Fri
2 stopsDelta
15h 02mMDW-OGG
8/22Thu
2 stopsDelta
16h 38mOGG-MDW
$678
10/24Thu
2 stopsDelta
15h 56mMDW-OGG
11/3Sun
2 stopsDelta
16h 51mOGG-MDW
$772
8/5Mon
2 stopsDelta
18h 35mMDW-OGG
8/12Mon
2 stopsDelta
15h 43mOGG-MDW
$923
7/27Sat
2 stopsDelta
18h 35mMDW-OGG
7/30Tue
2 stopsDelta
15h 22mOGG-MDW
$987
10/4Fri
2 stopsDelta
15h 41mMDW-OGG
10/12Sat
2 stopsDelta
15h 01mOGG-MDW
$1,002
7/24Wed
2 stopsDelta
15h 02mMDW-OGG
7/29Mon
2 stopsDelta
16h 39mOGG-MDW
$1,005
11/17Sun
2 stopsDelta
15h 56mMDW-OGG
11/23Sat
1 stopDelta
12h 42mOGG-MDW
$1,027
10/21Mon
2 stopsDelta
15h 56mMDW-OGG
10/26Sat
2 stopsDelta
15h 05mOGG-MDW
$1,032
7/2Tue
2 stopsDelta
18h 36mMDW-OGG
7/8Mon
2 stopsDelta
16h 39mOGG-MDW
$1,092
6/28Fri
3 stops
34h 57mMDW-OGG
7/5Fri
3 stops
34h 34mOGG-MDW
$1,673

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Recent one-way flight deals

7/10Wed
2 stopsDelta
15h 17mMDW-OGG
$416
8/31Sat
2 stopsDelta
15h 17mMDW-OGG
$516
8/31Sat
3 stopsWestJet
37h 01mMDW-OGG
$862

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Last minute flights from Midway to Maui

Last minute flight, train and bus deals

6/4Tue
multi-stopDelta
14h 24mMDW-OGG
6/11Tue
multi-stopDelta
15h 06mOGG-MDW
$952

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Chicago Midway Airport - Maui Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Maui - Chicago Midway Airport

Cabin classes:

$639
$728
$477
$37

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