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$205+ Cheap flights from Midway (MDW) to Hawaii

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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheap flight deals from Midway to Hawaii

Keep the following information in mind while searching for Midway to Hawaii flight deals. Data was last updated August 11, 2025.

Round-trip from

$477
(Southwest)

One-way from

$205
(Southwest)

Popular in

December

Cheapest in

January

Average price

$787
From Chicago Midway to Hawaii
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One-way flight from Chicago Midway to Hawaii
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Highest demand for flights based on searches. 3% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Midway to Hawaii

Cheapest flights from Midway to Hawaii
Explore the most affordable flight options available from Midway to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2025.

This Southwest deal was found by Cheapflights users on 8/9. 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.
Tue 12/25:15 amMDW - KOA
1 stop12h 25mSouthwest
Tue 12/99:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 8/9$477
This Southwest deal was found by Cheapflights users on 8/8. 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.
Wed 12/38:55 pmMDW - HNL
1 stop18h 25mSouthwest
Wed 12/108:00 amHNL - MDW
1 stop10h 55mSouthwest
Deal found 8/8$481
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 11/265:40 amMDW - OGG
2 stops13h 10mSouthwest
Fri 12/59:25 pmOGG - MDW
1 stop11h 55mSouthwest
Deal found 8/10$485
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 10/2011:00 amMDW - HNL
1 stop15h 00mSouthwest
Thu 10/309:10 pmHNL - MDW
1 stop13h 40mSouthwest
Deal found 8/10$487
This Delta deal was found by Cheapflights users on 8/10. 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.
Thu 11/279:30 amMDW - OGG
2 stops13h 53mDelta
Fri 12/51:45 pmOGG - MDW
2 stops15h 01mDelta
Deal found 8/10$487
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sat 9/138:25 amMDW - HNL
1 stop17h 35mSouthwest
Tue 9/239:05 pmHNL - MDW
1 stop10h 10mSouthwest
Deal found 8/9$488
This Delta deal was found by Cheapflights users on 8/10. 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.
Wed 9/179:20 amMDW - HNL
2 stops16h 15mDelta
Wed 10/81:15 pmHNL - MDW
2 stops14h 40mDelta
Deal found 8/10$494
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 9/106:10 amMDW - OGG
1 stop11h 15mSouthwest
Wed 9/178:25 pmOGG - MDW
1 stop10h 20mSouthwest
Deal found 8/9$505
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sun 11/97:45 amMDW - HNL
1 stop12h 30mSouthwest
Sat 11/159:55 pmHNL - MDW
1 stop10h 45mSouthwest
Deal found 8/9$506
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sun 10/265:15 amMDW - LIH
1 stop12h 40mSouthwest
Sun 11/29:10 pmLIH - MDW
1 stop10h 25mSouthwest
Deal found 8/9$506
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 12/35:15 amMDW - KOA
1 stop12h 25mSouthwest
Wed 12/109:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 8/9$508
This Southwest deal was found by Cheapflights users on 8/10. 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.
Tue 11/45:15 amMDW - OGG
2 stops14h 50mSouthwest
Wed 11/129:25 pmOGG - MDW
2 stops12h 40mSouthwest
Deal found 8/10$510

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Hawaii 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 August 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Hawaii that are best for you.

Fly from

Midway

Fly to

Hawaii

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 2/4

6:10 am-4:25 pm

2 stops14h 15m

Kahului

Wed 2/11

9:35 pm-3:00 pm

1 stop13h 25m

$480

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 11/26

5:40 am-2:50 pm

2 stops13h 10m

Kahului

Fri 12/5

9:25 pm-1:20 pm

1 stop11h 55m

$485

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 11/27

9:30 am-7:23 pm

2 stops13h 53m

Kahului

Fri 12/5

1:45 pm-8:46 am

2 stops15h 01m

$487

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/20

11:00 am-9:00 pm

1 stop15h 00m

Honolulu

Thu 10/30

9:10 pm-3:50 pm

1 stop13h 40m

$487

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/13

8:25 am-9:00 pm

1 stop17h 35m

Honolulu

Tue 9/23

9:05 pm-12:15 pm

1 stop10h 10m

$488

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/17

9:20 am-8:35 pm

2 stops16h 15m

Honolulu

Wed 10/8

1:15 pm-8:55 am

2 stops14h 40m

$494

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 9/10

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Wed 9/17

8:25 pm-11:45 am

1 stop10h 20m

$505

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 10/26

5:15 am-12:55 pm

1 stop12h 40m

Lihue

Sun 11/2

9:10 pm-11:35 am

1 stop10h 25m

$506

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 11/4

5:15 am-4:05 pm

2 stops14h 50m

Kahului

Wed 11/12

9:25 pm-2:05 pm

2 stops12h 40m

$510

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 10/28

6:05 am-1:00 pm

1 stop11h 55m

Kona Intl

Mon 11/3

9:15 pm-11:35 am

1 stop10h 20m

$510

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 57 results
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Best time to book a flight from Midway to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Hawaii

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $469). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $687). 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.

Reviews of airlines servicing Hawaii

Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated August 11, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Hawaii, such as Southwest and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

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

  • What are the most popular routes from Chicago Midway Airport to Hawaii?

    While some choose either Chicago Midway - Kahului or Chicago Midway - Lihue, Chicago Midway - Honolulu is the most popular route from Chicago Midway Airport to Hawaii.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Hawaii 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 Hawaii?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $469). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $687). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Hawaii

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Newark flights
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O'Hare Intl to Fort Lauderdale flights
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Midway to Dallas/Fort Worth flights
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Midway to Tampa flights
O'Hare Intl to George Bush Intcntl flights
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Midway to Denver flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Charlotte flights
Midway to Baltimore flights

Top 2 airlines flying from Midway to Hawaii

Discover the top 2 airlines that operate flights from Midway to Hawaii. 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$606FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$498Average$773FlexibilityNo cancel feeOn-time63%

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