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Midway

$259+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheap 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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$259
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$712
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
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One-way flight from O'ahu to Chicago Midway
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Highest demand for flights based on searches. 10% potential increase in price ($85 potential increase over avg. RT price).
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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 November 2025
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Find 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 November 20, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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 12/155:37 pmHNL - MDW
2 stops14h 57mDelta
Thu 1/16:00 amMDW - HNL
1 stop13h 04mDelta
Deal found 11/19$447
This Delta deal was found by Cheapflights users on 11/17. 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 12/2411:35 pmHNL - MDW
2 stops13h 44mDelta
Fri 1/26:00 amMDW - HNL
1 stop15h 25mDelta
Deal found 11/17$526
This Southwest deal was found by Cheapflights users on 11/18. 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 12/259:25 pmHNL - MDW
1 stop14h 15mSouthwest
Wed 12/318:20 amMDW - HNL
1 stop16h 40mSouthwest
Deal found 11/18$572
This Delta deal was found by Cheapflights users on 11/18. 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 11/252:19 pmHNL - MDW
2 stops14h 35mDelta
Tue 12/99:59 amMDW - HNL
2 stops15h 49mDelta
Deal found 11/18$600

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 November 20, 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

Thu 1/15

1:55 pm-8:52 am

2 stops14h 57m

Chicago Midway

Mon 1/19

6:00 am-3:11 pm

1 stop13h 11m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/12

4:44 pm-8:52 am

1 stop12h 08m

Chicago Midway

Sun 1/18

9:32 am-9:28 pm

2 stops15h 56m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/15

5:37 pm-12:34 pm

2 stops14h 57m

Chicago Midway

Thu 1/1

6:00 am-3:04 pm

1 stop13h 04m

$447

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/12

9:00 pm-2:45 pm

1 stop13h 45m

Chicago Midway

Sun 1/18

8:15 am-9:00 pm

1 stop16h 45m

$450

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 12/24

11:35 pm-5:19 pm

2 stops13h 44m

Chicago Midway

Fri 1/2

6:00 am-5:25 pm

1 stop15h 25m

$526

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

10:42 pm-3:18 pm

2 stops36h 36m

$259

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 12/26

11:35 pm-5:19 pm

2 stops13h 44m

$269

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/22

4:45 pm-8:49 am

1 stop12h 04m

$302

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 12/21

9:39 pm-1:59 pm

3 stops36h 20m

$311

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/29

9:36 pm-10:12 pm

3 stops44h 36m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 15 results
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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 November 20, 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 November 20, 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
8.0
Very good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 14h 57m. 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$516Average$778FlexibilityNo cancel feeOn-time63%

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