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$240+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$430
(Delta)

One-way from

$240
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$637
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
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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. 8% potential increase in price ($73 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 January 2026
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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/7. 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 1/306:00 amMDW - HNL
1 stop13h 10mDelta
Sun 2/84:45 pmHNL - MDW
2 stops16h 21mDelta
Deal found 1/7$430
This Southwest deal was found by Cheapflights users on 1/7. 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 2/238:05 amMDW - HNL
2 stops16h 55mSouthwest
Tue 3/39:55 pmHNL - MDW
2 stops14h 40mSouthwest
Deal found 1/7$431
This Delta deal was found by Cheapflights users on 1/8. 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 3/21:49 pmMDW - HNL
2 stops26h 06mDelta
Wed 3/1110:42 pmHNL - MDW
2 stops29h 08mDelta
Deal found 1/8$433
This Delta deal was found by Cheapflights users on 1/7. 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 2/39:33 amMDW - HNL
2 stops15h 55mDelta
Tue 2/101:55 pmHNL - MDW
2 stops14h 57mDelta
Deal found 1/7$435
This Southwest deal was found by Cheapflights users on 1/7. 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 2/210:30 amMDW - HNL
2 stops14h 30mSouthwest
Mon 2/99:00 pmHNL - MDW
1 stop12h 00mSouthwest
Deal found 1/7$436
This Delta deal was found by Cheapflights users on 1/8. 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 3/21:49 pmMDW - HNL
2 stops26h 06mDelta
Thu 3/54:50 pmHNL - MDW
1 stop13h 04mDelta
Deal found 1/8$441
This Delta deal was found by Cheapflights users on 1/7. 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 2/26:00 amMDW - HNL
2 stops19h 28mDelta
Thu 2/54:45 pmHNL - MDW
1 stop12h 07mDelta
Deal found 1/7$442
This Southwest deal was found by Cheapflights users on 1/5. 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.
Wed 4/2210:05 amMDW - HNL
1 stop15h 55mSouthwest
Mon 4/271:00 pmHNL - MDW
1 stop11h 50mSouthwest
Deal found 1/5$451
This Southwest deal was found by Cheapflights users on 1/7. 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 3/38:15 amMDW - HNL
1 stop16h 45mSouthwest
Sat 3/79:15 amHNL - MDW
1 stop15h 45mSouthwest
Deal found 1/7$452
This Delta deal was found by Cheapflights users on 1/8. 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 3/26:00 amMDW - HNL
1 stop13h 11mDelta
Fri 3/67:45 amHNL - MDW
2 stops28h 29mDelta
Deal found 1/8$453

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 January 8, 2026.
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

Tue 2/3

9:33 am-9:28 pm

2 stops15h 55m

Honolulu

Tue 2/10

5:15 pm-9:08 am

1 stop11h 53m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 2/1

9:33 am-9:28 pm

2 stops15h 55m

Honolulu

Sun 2/8

5:15 pm-9:08 am

1 stop11h 53m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 3/18

9:35 am-8:53 pm

2 stops16h 18m

Honolulu

Wed 3/25

4:20 pm-8:50 am

1 stop11h 30m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 1/31

9:33 am-9:28 pm

2 stops15h 55m

Honolulu

Wed 2/4

5:15 pm-9:08 am

1 stop11h 53m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 3/4

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Sun 3/8

4:20 pm-8:50 am

1 stop11h 30m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/2

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Thu 3/12

3:46 pm-8:53 am

1 stop12h 07m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 2/17

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Tue 2/24

5:15 pm-9:06 am

1 stop11h 51m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 2/22

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Thu 2/26

5:15 pm-9:06 am

1 stop11h 51m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 3/1

10:15 pm-11:15 am

1 stop17h 00m

Honolulu

Wed 3/4

9:30 pm-5:35 pm

2 stops16h 05m

$447

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 3/3

8:15 am-9:00 pm

1 stop16h 45m

Honolulu

Sat 3/7

9:15 am-5:00 am

1 stop15h 45m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 21 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to O'ahu (average of $310). Flying from Chicago Midway Airport to O'ahu in July is currently the most expensive (average of $886). 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 January 8, 2026.
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
4,250 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

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
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

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
Delta
7.9
Good
8,025 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

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 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.

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

    There are many flights that can get you from Chicago Midway Airport to O'ahu in 15h 55m. Fly via Delta to get the fastest option. There are 4243 mi between Chicago Midway Airport and O'ahu.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to O'ahu (average of $310). Flying from Chicago Midway Airport to O'ahu in July is currently the most expensive (average of $886). 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$429Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$598Average$767FlexibilityNo cancel feeOn-time63%

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