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$231+ Cheap flights from Hawaii to Midway (MDW)

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Hawaii to Midway

Keep the following information in mind while searching for Hawaii to Midway flight deals. Data was last updated August 14, 2025.

Round-trip from

$428
(Delta)

One-way from

$231
(Southwest)

Popular in

July

Cheapest in

November

Average price

$678
From Hawaii to Chicago Midway
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One-way flight from Hawaii to Chicago Midway
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Highest demand for flights based on searches. 10% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 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 Hawaii to Midway

Cheapest flights from Hawaii to Midway
Explore the most affordable flight options available from Hawaii to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 11/74:45 pmHNL - MDW
1 stop11h 55mDelta
Tue 11/119:30 amMDW - HNL
2 stops16h 15mDelta
Deal found 8/14$428
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/291:00 pmHNL - MDW
2 stops14h 53mDelta
Thu 10/309:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 8/13$434
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 11/74:45 pmHNL - MDW
1 stop11h 55mDelta
Mon 11/106:00 amMDW - HNL
1 stop13h 02mDelta
Deal found 8/14$453
This Southwest deal was found by Cheapflights users on 8/13. 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.
Fri 9/128:05 amHNL - MDW
1 stop11h 25mSouthwest
Tue 9/161:35 pmMDW - HNL
1 stop12h 25mSouthwest
Deal found 8/13$454
This Delta deal was found by Cheapflights users on 8/14. 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 11/62:20 pmHNL - MDW
2 stops14h 35mDelta
Mon 11/106:00 amMDW - HNL
1 stop13h 02mDelta
Deal found 8/14$458
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 10/61:20 pmHNL - MDW
2 stops14h 20mDelta
Tue 10/149:35 amMDW - HNL
2 stops15h 51mDelta
Deal found 8/14$464
This Southwest deal was found by Cheapflights users on 8/12. 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 10/229:10 pmHNL - MDW
1 stop10h 25mSouthwest
Mon 10/279:25 pmMDW - HNL
1 stop17h 55mSouthwest
Deal found 8/12$481
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/291:00 pmHNL - MDW
2 stops14h 53mDelta
Tue 10/286:00 amMDW - HNL
1 stop12h 32mDelta
Deal found 8/13$488
This Southwest deal was found by Cheapflights users on 8/13. 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.
Fri 9/128:05 amHNL - MDW
1 stop11h 25mSouthwest
Fri 9/1912:10 pmMDW - HNL
1 stop13h 50mSouthwest
Deal found 8/13$491
This Delta deal was found by Cheapflights users on 8/13. 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 10/11:15 pmHNL - MDW
2 stops14h 25mDelta
Fri 10/319:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 8/13$494
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/291:00 pmHNL - MDW
2 stops14h 53mDelta
Mon 10/277:10 pmMDW - HNL
2 stops21h 07mDelta
Deal found 8/13$504
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/291:00 pmHNL - MDW
2 stops14h 53mDelta
Sat 11/14:23 pmMDW - HNL
2 stops34h 03mDelta
Deal found 8/13$505

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hawaii to Midway 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 14, 2025.
Use the filters below to find and compare flights from Hawaii to Chicago Midway Airport that are best for you.

Fly from

Hawaii

Fly to

Midway

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 11/7

4:45 pm-8:40 am

1 stop11h 55m

Chicago Midway

Tue 11/11

9:30 am-9:45 pm

2 stops16h 15m

$428

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 9/29

1:00 pm-8:53 am

2 stops14h 53m

Chicago Midway

Thu 10/30

9:20 am-8:26 pm

2 stops16h 06m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 9/30

1:15 pm-8:40 am

2 stops14h 25m

Chicago Midway

Tue 10/28

9:35 am-7:09 pm

2 stops14h 34m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 9/30

1:15 pm-8:53 am

2 stops14h 38m

Chicago Midway

Wed 10/29

9:20 am-8:26 pm

2 stops16h 06m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 9/29

1:00 pm-8:53 am

2 stops14h 53m

Chicago Midway

Fri 10/31

9:20 am-8:26 pm

2 stops16h 06m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sat 11/8

2:20 pm-8:45 am

2 stops14h 25m

Chicago Midway

Wed 11/12

9:30 am-8:20 pm

2 stops14h 50m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 9/12

1:00 pm-8:53 am

2 stops14h 53m

Chicago Midway

Tue 9/16

9:20 am-8:35 pm

2 stops16h 15m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 9/30

1:15 pm-8:53 am

2 stops14h 38m

Chicago Midway

Thu 10/30

9:20 am-8:26 pm

2 stops16h 06m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

10:15 pm-6:25 pm

2 stops15h 10m

Chicago Midway

Fri 10/31

9:20 am-8:26 pm

2 stops16h 06m

$434

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 11/6

2:20 pm-8:55 am

2 stops14h 35m

Chicago Midway

Tue 11/11

9:30 am-9:45 pm

2 stops16h 15m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 47 results
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Best time to book a flight from Hawaii to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Hawaii 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 Hawaii to Chicago Midway Airport

What is the cheapest time of day to fly from HI to MDW?

Find hourly flight availability from Hawaii to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Hawaii to Chicago Midway Airport as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Hawaii to Midway. 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 Hawaii to Chicago Midway Airport?

    Most travelers choose Honolulu - Chicago Midway, Kahului - Chicago Midway or Kona Intl - Chicago Midway when deciding on the best route from Hawaii to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Hawaii to Chicago Midway Airport (average of $160). Flying from Hawaii to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Hawaii to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Baltimore to O'Hare Intl flights
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LaGuardia to Midway flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to Midway flights
Austin to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
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Atlanta to O'Hare Intl flights
Atlanta to Midway flights
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San Jose to O'Hare Intl flights
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Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Love Field to Midway flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
San Diego to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
Seattle to Midway flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Orlando to Midway flights
Cleveland to O'Hare Intl flights
Los Angeles to Midway flights
Oakland to O'Hare Intl flights
Boston to Midway flights

Top airline flying from Hawaii to Midway

Discover the top airline that operate flights from Hawaii to Midway. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$606Average$788FlexibilityNo cancel feeOn-time63%

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