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$276+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

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.
Mon 12/89:34 amMDW - HNL
2 stops14h 55mDelta
Sat 12/134:45 pmHNL - MDW
1 stop12h 09mDelta
Deal found 11/17$526
This Southwest deal was found by Cheapflights users on 11/20. 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 12/318:20 amMDW - HNL
1 stop16h 40mSouthwest
Wed 1/149:00 pmHNL - MDW
1 stop14h 30mSouthwest
Deal found 11/20$539
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.
Thu 12/49:59 amMDW - HNL
2 stops15h 49mDelta
Thu 12/112:26 pmHNL - MDW
2 stops14h 28mDelta
Deal found 11/19$544
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:15 amMDW - HNL
1 stop13h 45mSouthwest
Wed 12/109:55 pmHNL - MDW
1 stop15h 20mSouthwest
Deal found 11/19$545
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.
Tue 12/29:59 amMDW - HNL
2 stops15h 49mDelta
Wed 12/102:26 pmHNL - MDW
2 stops14h 28mDelta
Deal found 11/17$561
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 12/86:00 amMDW - HNL
1 stop13h 04mDelta
Mon 12/155:37 pmHNL - MDW
2 stops14h 57mDelta
Deal found 11/19$576
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.
Mon 12/15:00 amMDW - HNL
1 stop12h 30mSouthwest
Wed 12/109:55 pmHNL - MDW
1 stop15h 20mSouthwest
Deal found 11/18$580

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$522
(Southwest)

One-way from

$276
(Southwest)

Popular in

December

Cheapest in

February

Average price

$832
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
Search Deals
From Chicago Midway to O'ahu
Search Deals
One-way flight from Chicago Midway to O'ahu
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 20, 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

Tue 1/20

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Tue 1/27

1:17 pm-8:52 am

2 stops15h 35m

$532

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 2/8

9:33 am-9:28 pm

2 stops15h 55m

Honolulu

Sun 3/8

4:20 pm-12:35 pm

2 stops15h 15m

$538

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 1/7

8:25 am-4:30 pm

1 stop12h 05m

Honolulu

Sun 1/11

9:00 pm-2:45 pm

1 stop13h 45m

$543

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/2

6:00 am-5:25 pm

1 stop15h 25m

Honolulu

Thu 1/8

5:15 pm-12:48 pm

2 stops15h 33m

$546

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/8

8:10 am-9:00 pm

2 stops16h 50m

Honolulu

Mon 1/12

9:30 pm-2:45 pm

2 stops13h 15m

$564

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 2/16

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Tue 2/24

5:15 pm-12:48 pm

2 stops15h 33m

$566

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/29

8:15 am-9:00 pm

1 stop16h 45m

Honolulu

Tue 2/10

9:00 pm-2:45 pm

1 stop13h 45m

$573

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/23

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Sat 1/31

4:44 pm-8:52 am

1 stop12h 08m

$577

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 12/1

5:00 am-1:30 pm

1 stop12h 30m

Honolulu

Wed 12/10

9:55 pm-5:15 pm

1 stop15h 20m

$580

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 2/1

6:00 am-8:39 pm

2 stops18h 39m

Honolulu

Sat 2/7

1:17 pm-8:52 am

2 stops15h 35m

$582

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 23 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 $324). 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 November 20, 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
4,251 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
Delta
7.9
Good
8,002 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 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 12h 05m. Fly via Delta or Southwest to get the fastest option. There are 4243 mi between Chicago Midway Airport and O'ahu. This flight may include one or multiple stops.

  • 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 $324). 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$442Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$767FlexibilityNo cancel feeOn-time63%

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