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$231+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$474
(Delta)

One-way from

$231
(Southwest)

Popular in

December

Cheapest in

February

Average price

$866
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. 4% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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 10mDelta
Wed 9/244:10 pmHNL - MDW
2 stops15h 18mDelta
Deal found 7/28$474
This Southwest deal was found by Cheapflights users on 7/29. 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.
Tue 8/196:10 amMDW - OGG
1 stop11h 15mSouthwest
Tue 9/28:30 pmOGG - MDW
1 stop10h 45mSouthwest
Deal found 7/29$480
This Southwest deal was found by Cheapflights users on 7/29. 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.
Tue 8/191:35 pmMDW - HNL
1 stop12h 25mSouthwest
Tue 8/269:10 pmHNL - MDW
1 stop16h 55mSouthwest
Deal found 7/29$481
This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 9/17:55 amMDW - LIH
2 stops15h 15mSouthwest
Wed 9/108:40 pmLIH - MDW
1 stop12h 50mSouthwest
Deal found 7/29$491
This Southwest deal was found by Cheapflights users on 7/28. 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 7/28$508
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:00 amMDW - KOA
2 stops17h 53mDelta
Thu 11/69:30 pmKOA - MDW
2 stops31h 10mDelta
Deal found 7/29$613
This Delta deal was found by Cheapflights users on 7/28. 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.
Sun 9/289:35 amMDW - LIH
2 stops14h 24mDelta
Mon 10/69:40 pmLIH - MDW
2 stops15h 03mDelta
Deal found 7/28$614
This Delta deal was found by Cheapflights users on 7/28. 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 9/46:00 amMDW - OGG
2 stops17h 40mDelta
Mon 9/812:00 pmOGG - MDW
2 stops15h 35mDelta
Deal found 7/28$685
This Southwest deal was found by Cheapflights users on 7/27. 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 - ITO
2 stops16h 55mSouthwest
Sat 11/86:00 amITO - MDW
2 stops12h 45mSouthwest
Deal found 7/27$694
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/279:20 amMDW - ITO
2 stops40h 10mDelta
Mon 9/299:43 amITO - MDW
2 stops26h 52mDelta
Deal found 7/28$906

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 July 30, 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

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/17

9:20 am-8:30 pm

2 stops16h 10m

Honolulu

Wed 9/24

4:10 pm-12:28 pm

2 stops15h 18m

$474

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 8/19

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Wed 8/27

8:25 pm-2:30 pm

1 stop13h 05m

$480

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 8/19

1:35 pm-9:00 pm

1 stop12h 25m

Honolulu

Tue 8/26

9:10 pm-7:05 pm

1 stop16h 55m

$481

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 9/1

7:55 am-6:10 pm

2 stops15h 15m

Lihue

Wed 9/10

8:40 pm-2:30 pm

1 stop12h 50m

$491

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 9/13

8:25 am-6:10 pm

2 stops14h 45m

Kona Intl

Tue 9/23

8:30 pm-11:45 am

1 stop10h 15m

$579

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 9/28

9:35 am-6:59 pm

2 stops14h 24m

Lihue

Mon 10/6

9:40 pm-5:43 pm

2 stops15h 03m

$614

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 9/2

9:15 am-7:00 pm

2 stops14h 45m

Kona Intl

Tue 9/9

8:41 pm-6:37 pm

2 stops16h 56m

$634

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 9/4

6:00 am-6:40 pm

2 stops17h 40m

Kahului

Mon 9/8

12:00 pm-8:35 am

2 stops15h 35m

$685

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 8/19

6:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

Fri 8/22

6:00 am-11:25 pm

2 stops12h 25m

$714

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

9:20 am-8:30 pm

2 stops40h 10m

Hilo Intl

Mon 9/29

9:43 am-5:35 pm

2 stops26h 52m

$906

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 20 results
1
2

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 July 30, 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
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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

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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 Seattle flights
Midway to Sky Harbor Intl flights
Midway to Los Angeles flights
O'Hare Intl to Burbank 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$606FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$498Average$773FlexibilityNo cancel feeOn-time63%

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