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$292+ Cheap flights from Midway (MDW) to Maui

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
feb. 4 — feb. 111
mar. 2/4
mar. 2/11
1 adult, Economy
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Cheap flight deals from Midway to Maui

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Maui (zzFUK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$441
(Delta)

One-way from

$292
(Delta)

Popular in

March

Cheapest in

September

Average price

$573
Provider with most accurate pricing for Chicago (CHI)-Kahului flight deals.
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From Chicago Midway to Maui
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One-way flight from Chicago Midway to Maui
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Highest demand for flights based on searches. 6% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Find flight deals from Midway to Maui

Cheapest flights from Midway to Maui
Explore the most affordable flight options available from Midway to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 30, 2025.

This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/269:33 amMDW - OGG
2 stops14h 22mDelta
lun. 3/35:25 pmOGG - MDW
1 stop12h 47mDelta
Deal found 1/30$462
This Kissandfly.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/36:40 amMDW - OGG
2 stops18h 03mMultiple Airlines
lun. 3/1012:30 pmOGG - MDW
2 stops22h 02mMultiple Airlines
Deal found 1/30$493
This Southwest deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/257:20 amMDW - OGG
1 stop13h 00mSouthwest
jue. 3/68:50 amOGG - MDW
1 stop10h 40mSouthwest
Deal found 1/29$549

Find flights from Midway to Maui within your budget

Customize your flight search to find flights from Midway to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 30, 2025.

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Fly to

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Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

dom. 3/2

6:00 am-5:39 pm

1 stop15h 39m

Kahului

mié. 3/5

2:25 pm-8:51 am

2 stops14h 26m

$441

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

lun. 3/3

6:40 am-8:43 pm

2 stops18h 03m

Kahului

lun. 3/10

12:30 pm-3:32 pm

2 stops22h 02m

$493

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mar. 2/25

7:20 am-4:20 pm

1 stop13h 00m

Kahului

jue. 3/6

8:50 am-11:30 pm

1 stop10h 40m

$549

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

vie. 2/28

6:00 am-5:39 pm

1 stop15h 39m

$292

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mié. 4/16

5:35 am-1:00 pm

1 stop12h 25m

$293

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mar. 2/18

7:05 am-8:43 pm

2 stops17h 38m

$334

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

sáb. 2/22

6:40 am-8:58 pm

3 stops18h 18m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Best time to book a flight from Midway to Maui

Have a flexible travel schedule? Discover the best time to fly to Maui from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway to Maui

Get recent, data-driven insights about flights from Midway to Maui including ideal travel times, pricing trends, and more.

Rainfall in Maui by month

Plan your trip to Maui by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maui ranges from 0.1 - 3.8 inches per month. January is typically the wettest month, when rainfall can reach 3.8 in. June is typically the driest time to visit Maui when rainfall is around 0.1 in.

Temperature in Maui by month

Plan your trip to Maui by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maui, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 71.6 F).

Reviews of airlines servicing Maui

Get insights into the airlines that provide service to Maui. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maui. Reviews last updated enero 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier from Chicago to Maui by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.0
Okay
3,424 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Midway to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Maui one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $292. Users have also found prices from $293 and $334 on Southwest and Frontier, respectively.

  • Can I find deals for flights from Midway to Maui that include hotel bookings?

    Yes. In addition to deals on Midway to Maui flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Maui?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Maui.

  • Can I find deals for business class flights from Midway to Maui?

    Yes. Cheapflights offers flight deals from Midway to Maui by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Maui?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Maui (average of $391). Flying from Chicago Midway Airport to Maui in June is currently the most expensive (average of $576). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top airline flying from Midway to Maui

Discover the top airline that operate flights from Midway to Maui. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$741FlexibilityNo cancel feeOn-time63%
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