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$242+ Cheap flights from Midway (MDW) to O'ahu

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

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

Round-trip from

$476
(Southwest)

One-way from

$242
(Southwest)

Popular in

December

Cheapest in

January

Average price

$787
From Chicago Midway to O'ahu
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One-way flight from Chicago Midway to O'ahu
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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 O'ahu

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

This Southwest deal was found by Cheapflights users on 8/11. 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 10/279:25 pmMDW - HNL
1 stop17h 55mSouthwest
Sun 11/28:00 amHNL - MDW
1 stop13h 30mSouthwest
Deal found 8/11$476
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/110:15 pmMDW - HNL
1 stop17h 05mSouthwest
Fri 12/59:25 pmHNL - MDW
1 stop10h 35mSouthwest
Deal found 8/14$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.
Wed 9/36:00 amMDW - HNL
1 stop12h 15mDelta
Thu 9/43:00 pmHNL - MDW
1 stop12h 35mDelta
Deal found 8/13$483
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.
Tue 9/239:20 amMDW - HNL
2 stops16h 15mDelta
Tue 10/72:50 pmHNL - MDW
1 stop12h 50mDelta
Deal found 8/14$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.
Sun 11/29:30 pmMDW - HNL
1 stop17h 50mSouthwest
Sun 11/99:55 pmHNL - MDW
1 stop10h 45mSouthwest
Deal found 8/13$491
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:00 amMDW - HNL
1 stop15h 00mSouthwest
Fri 10/319:00 pmHNL - MDW
2 stops14h 25mSouthwest
Deal found 8/14$493
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 10/89:25 pmMDW - HNL
1 stop17h 55mSouthwest
Wed 10/158:05 amHNL - MDW
1 stop11h 20mSouthwest
Deal found 8/12$499
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 11/106:45 pmMDW - HNL
2 stops21h 23mDelta
Thu 11/131:35 pmHNL - MDW
2 stops15h 11mDelta
Deal found 8/13$504
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:40 amMDW - HNL
1 stop18h 20mSouthwest
Mon 10/139:10 pmHNL - MDW
1 stop10h 20mSouthwest
Deal found 8/14$506
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.
Mon 10/2011:00 amMDW - HNL
1 stop15h 00mSouthwest
Mon 10/279:10 pmHNL - MDW
1 stop10h 20mSouthwest
Deal found 8/12$509

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to O'ahu 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 Chicago Midway Airport to O'ahu that are best for you.

Fly from

Midway

Fly to

O'ahu

Route

Depart

Return

Price

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/27

9:25 pm-10:20 am

1 stop17h 55m

Honolulu

Sun 11/2

8:00 am-1:30 am

1 stop13h 30m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop12h 32m

Honolulu

Fri 11/7

4:45 pm-8:40 am

1 stop11h 55m

$483

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 10/31

6:00 am-1:32 pm

1 stop12h 32m

Honolulu

Fri 11/7

4:45 pm-8:40 am

1 stop11h 55m

$483

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/3

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Thu 9/4

3:00 pm-8:35 am

1 stop12h 35m

$483

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/27

8:25 am-9:00 pm

1 stop17h 35m

Honolulu

Thu 10/2

8:05 am-12:35 am

1 stop11h 30m

$488

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/23

9:35 am-8:35 pm

2 stops16h 00m

Honolulu

Tue 10/7

2:50 pm-8:40 am

1 stop12h 50m

$488

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop12h 32m

Honolulu

Thu 11/13

1:35 pm-8:46 am

2 stops15h 11m

$488

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/17

6:00 am-1:23 pm

1 stop12h 23m

Honolulu

Wed 9/24

1:00 pm-8:53 am

2 stops14h 53m

$488

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/10

6:00 am-3:02 pm

1 stop13h 02m

Honolulu

Thu 11/13

1:35 pm-8:46 am

2 stops15h 11m

$488

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 10/31

6:00 am-1:32 pm

1 stop12h 32m

Honolulu

Tue 11/18

1:55 pm-8:46 am

2 stops14h 51m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 22 results
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Best time to book a flight from Midway to O'ahu

Have a flexible travel schedule? Discover the best time to fly to O'ahu 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 O'ahu

What is the cheapest month to book a flight from Chicago Midway Airport to O'ahu?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to O'ahu (average of $469). Flying from Chicago Midway Airport to O'ahu 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 O'ahu

Get insights into the airlines that provide service to O'ahu. 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 O'ahu. Reviews last updated August 14, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to O'ahu, such as Southwest and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

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

  • Can I find deals for flights from Midway to O'ahu that include hotel bookings?

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

  • How can I find direct flights from Midway to O'ahu?

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

  • Can I find deals for business class flights from Midway to O'ahu?

    Yes. Cheapflights offers flight deals from Midway to O'ahu 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 O'ahu?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to O'ahu (average of $469). Flying from Chicago Midway Airport to O'ahu 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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Top 2 airlines flying from Midway to O'ahu

Discover the top 2 airlines that operate flights from Midway to O'ahu. 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
DeltaCheapest$427Average$606FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$559Average$764FlexibilityNo cancel feeOn-time63%

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