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Midway

$262+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Nov 4 — Nov 111
Tue 11/4
Tue 11/11
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 October 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$479
(Delta)

One-way from

$263
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$541
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. 13% potential increase in price ($112 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 October 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 October 5, 2025.

This Southwest deal was found by Cheapflights users on 10/5. 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 10/319:10 pmHNL - MDW
1 stop14h 40mSouthwest
Mon 11/38:20 amMDW - HNL
1 stop16h 40mSouthwest
Deal found 10/5$479
This Delta deal was found by Cheapflights users on 10/5. 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 10/313:10 pmHNL - MDW
1 stop13h 35mDelta
Mon 11/39:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 10/5$484
This Southwest deal was found by Cheapflights users on 10/5. 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 11/68:00 amHNL - MDW
1 stop13h 30mSouthwest
Wed 11/128:20 amMDW - HNL
1 stop16h 40mSouthwest
Deal found 10/5$511
This Delta deal was found by Cheapflights users on 10/4. 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 10/283:10 pmHNL - MDW
1 stop13h 35mDelta
Thu 10/306:00 amMDW - HNL
1 stop12h 32mDelta
Deal found 10/4$524
This Delta deal was found by Cheapflights users on 10/5. 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
Wed 11/129:41 amMDW - HNL
2 stops16h 08mDelta
Deal found 10/5$535
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/11:00 pmHNL - MDW
2 stops42h 30mMultiple Airlines
Sat 11/82:57 pmMDW - HNL
1 stop24h 56mMultiple Airlines
Deal found 10/4$553
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/29:35 pmHNL - MDW
2 stops20h 36mMultiple Airlines
Sun 11/99:00 amMDW - HNL
1 stop30h 53mMultiple Airlines
Deal found 10/3$565
This Delta deal was found by Cheapflights users on 10/5. 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 12/154:45 pmHNL - MDW
1 stop12h 09mDelta
Thu 1/16:00 amMDW - HNL
1 stop13h 04mDelta
Deal found 10/5$569

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 October 5, 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

Fri 11/7

4:45 pm-8:40 am

1 stop11h 55m

Chicago Midway

Tue 11/11

6:00 am-3:01 pm

1 stop13h 01m

$479

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/31

4:15 pm-12:31 pm

2 stops15h 16m

Chicago Midway

Mon 11/3

9:20 am-9:26 pm

2 stops16h 06m

$490

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 11/6

8:00 am-1:30 am

1 stop13h 30m

Chicago Midway

Wed 11/12

5:15 am-4:10 pm

2 stops14h 55m

$516

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 10/28

3:10 pm-9:45 am

1 stop13h 35m

Chicago Midway

Thu 10/30

6:00 am-1:32 pm

1 stop12h 32m

$524

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 11/6

2:20 pm-8:55 am

2 stops14h 35m

Chicago Midway

Wed 11/12

9:41 am-9:49 pm

2 stops16h 08m

$535

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sat 1/31

8:10 am-5:05 am

1 stop16h 55m

$262

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 12/16

4:06 pm-2:32 pm

2 stops42h 26m

$267

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 12/16

9:55 pm-5:15 pm

1 stop15h 20m

$272

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 12/23

4:45 pm-8:49 am

1 stop12h 04m

$285

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/22

4:45 pm-8:49 am

1 stop12h 04m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

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 October 5, 2025.

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

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 October 5, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta 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
4,237 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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 11h 55m. Delta provides one of the quickest options available for as low as $479. O'ahu and Chicago Midway Airport are separated by a distance of 4243 mi. This flight may include one or multiple stops.

  • 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.

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

    Currently, April is the cheapest month in which you can book a flight from O'ahu to Chicago Midway Airport (average of $160). Flying from O'ahu 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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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 October 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$516Average$778FlexibilityNo cancel feeOn-time63%

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