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Midway

$281+ Cheap flights from O'ahu 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from O'ahu to Midway

Cheapest flights from O'ahu to Midway
Explore the most affordable flight options available from O'ahu to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Delta deal was found by Cheapflights users on 12/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:00 pmHNL - MDW
1 stop12h 54mDelta
Thu 1/16:00 amMDW - HNL
1 stop15h 00mDelta
Deal found 12/12$657
This Southwest deal was found by Cheapflights users on 12/9. 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 12/99:00 pmHNL - MDW
1 stop14h 00mSouthwest
Mon 12/155:15 amMDW - HNL
1 stop12h 05mSouthwest
Deal found 12/9$750
This Southwest deal was found by Cheapflights users on 12/9. 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.
Fri 12/128:00 amHNL - MDW
1 stop13h 30mSouthwest
Sun 12/149:45 pmMDW - HNL
1 stop17h 35mSouthwest
Deal found 12/9$763
This Southwest deal was found by Cheapflights users on 12/10. 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 12/239:55 pmHNL - MDW
1 stop15h 20mSouthwest
Thu 12/2510:05 amMDW - HNL
2 stops14h 55mSouthwest
Deal found 12/10$820

Find flight deals from O'ahu to Midway

Keep the following information in mind while searching for O'ahu to Midway flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$421
(Southwest)

One-way from

$281
(Delta)

Popular in

July

Cheapest in

September

Average price

$724
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From O'ahu to Chicago Midway
Search Deals
One-way flight from O'ahu to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'ahu 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 December 12, 2025.
Use the filters below to find and compare flights from O'ahu to Chicago Midway Airport that are best for you.

Fly from

O'ahu

Fly to

Midway

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 1/20

1:55 pm-9:08 am

2 stops15h 13m

Chicago Midway

Wed 1/28

6:00 am-3:10 pm

1 stop13h 10m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 1/20

1:55 pm-9:08 am

2 stops15h 13m

Chicago Midway

Tue 1/27

6:00 am-3:10 pm

1 stop13h 10m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 1/23

4:44 pm-11:05 am

2 stops14h 21m

Chicago Midway

Wed 1/28

6:00 am-3:10 pm

1 stop13h 10m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 5/7

11:05 am-6:00 am

1 stop13h 55m

Chicago Midway

Tue 5/12

7:30 am-9:00 pm

2 stops18h 30m

$455

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/12

4:50 pm-10:27 am

1 stop13h 37m

Chicago Midway

Sun 1/18

9:32 am-9:28 pm

2 stops15h 56m

$493

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 4/14

4:10 pm-12:30 pm

2 stops15h 20m

$307

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/23

3:50 pm-9:55 am

1 stop13h 05m

$336

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/1

3:45 pm-8:46 am

1 stop12h 01m

$336

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 6/5

12:15 pm-5:40 am

1 stop12h 25m

$357

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 12/25

9:25 pm-3:40 pm

1 stop14h 15m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 13 results
1
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Best time to book a flight from O'ahu to Midway

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

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

Find hourly flight availability from O'ahu 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 December 12, 2025.

One of the essential ways to save on airfare from O'ahu to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 39% on airfare.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 12, 2025.
Peruse reviews from past customers who have flown with Southwest from O'ahu to Chicago Midway Airport to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

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

  • How long is the flight from O'ahu to Chicago Midway Airport?

    A quick flight from O'ahu to Chicago Midway Airport can take about 15h 13m. Delta provides one of the quickest options available for as low as $429. O'ahu and Chicago Midway Airport are separated by a distance of 4243 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from O'ahu 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from O'ahu to Midway

Discover the top airline that operate flights from O'ahu 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$788FlexibilityNo cancel feeOn-time63%

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