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$245+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Nov 4 — Nov 111
Tue 11/4
Tue 11/11
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 October 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$468
(Delta)

One-way from

$245
(Delta)

Popular in

December

Cheapest in

February

Average price

$635
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. 5% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 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 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 October 5, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amMDW - HNL
1 stop12h 32mDelta
Thu 11/132:19 pmHNL - MDW
2 stops14h 42mDelta
Deal found 10/3$468
This Southwest deal was found by Cheapflights users on 10/2. 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 10/2411:00 amMDW - HNL
1 stop15h 00mSouthwest
Thu 11/138:00 amHNL - MDW
1 stop13h 30mSouthwest
Deal found 10/2$473
This Delta deal was found by Cheapflights users on 10/2. 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 12/39:59 amMDW - HNL
2 stops15h 49mDelta
Tue 12/92:45 pmHNL - MDW
2 stops14h 34mDelta
Deal found 10/2$474
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/268:00 amMDW - HNL
2 stops18h 00mSouthwest
Fri 11/148:00 amHNL - MDW
1 stop13h 30mSouthwest
Deal found 10/3$477
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:05 amMDW - HNL
1 stop11h 05mSouthwest
Fri 10/319:10 pmHNL - MDW
1 stop14h 40mSouthwest
Deal found 10/3$479
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:00 amMDW - HNL
1 stop12h 32mDelta
Tue 11/112:19 pmHNL - MDW
2 stops14h 42mDelta
Deal found 10/3$484
This Southwest deal was found by Cheapflights users on 10/2. 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 12/108:20 amMDW - HNL
1 stop16h 40mSouthwest
Tue 12/169:55 pmHNL - MDW
2 stops14h 25mSouthwest
Deal found 10/2$498
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.
Mon 10/2710:56 pmMDW - HNL
1 stop17h 57mMultiple Airlines
Fri 10/317:43 amHNL - MDW
2 stops26h 14mMultiple Airlines
Deal found 10/4$499
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.
Mon 11/38:30 amMDW - HNL
2 stops30h 35mMultiple Airlines
Wed 11/1211:04 amHNL - MDW
1 stop26h 18mMultiple Airlines
Deal found 10/3$502
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/28:20 amMDW - HNL
1 stop16h 40mSouthwest
Tue 12/98:00 amHNL - MDW
1 stop10h 55mSouthwest
Deal found 10/4$511
This Delta deal was found by Cheapflights users on 10/2. 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 12/109:59 amMDW - HNL
2 stops15h 49mDelta
Tue 12/1611:15 pmHNL - MDW
2 stops15h 03mDelta
Deal found 10/2$514

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 October 5, 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

Mon 11/3

6:00 am-2:32 pm

1 stop12h 32m

Honolulu

Thu 11/13

2:19 pm-9:01 am

2 stops14h 42m

$468

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 12/3

9:59 am-9:48 pm

2 stops15h 49m

Honolulu

Tue 12/9

2:45 pm-9:19 am

2 stops14h 34m

$474

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 12/2

8:20 am-9:00 pm

1 stop16h 40m

Honolulu

Wed 12/10

12:35 pm-5:05 am

2 stops12h 30m

$477

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 11/4

9:20 am-9:26 pm

2 stops16h 06m

Honolulu

Tue 11/11

11:25 pm-6:18 pm

2 stops14h 53m

$490

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 11/2

9:35 am-9:26 pm

2 stops15h 51m

Honolulu

Tue 11/11

11:25 pm-6:18 pm

2 stops14h 53m

$490

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 11/4

9:35 am-8:09 pm

2 stops14h 34m

Honolulu

Thu 11/13

2:19 pm-9:01 am

2 stops14h 42m

$490

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 12/10

8:20 am-9:00 pm

1 stop16h 40m

Honolulu

Tue 12/16

9:55 pm-4:20 pm

2 stops14h 25m

$498

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 11/5

9:20 am-9:26 pm

2 stops16h 06m

Honolulu

Fri 11/14

5:00 pm-9:53 am

1 stop12h 53m

$516

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 11/13

9:34 am-8:15 pm

2 stops14h 41m

Honolulu

Wed 11/19

5:00 pm-12:34 pm

2 stops15h 34m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/3

9:20 am-9:26 pm

2 stops16h 06m

Honolulu

Mon 11/10

2:19 pm-9:01 am

2 stops14h 42m

$522

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Showing 1-10 of 18 results
1
2

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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to O'ahu (average of $469). Flying from Chicago Midway Airport to O'ahu in June is currently the most expensive (average of $687). 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 October 5, 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
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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

Boarding

8.1

Comfort

8.0

Crew

8.6

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

Boarding

8.1

Comfort

8.0

Crew

8.6

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 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 32m. 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to O'ahu (average of $469). Flying from Chicago Midway Airport to O'ahu in June is currently the most expensive (average of $687). 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 October 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$760FlexibilityNo cancel feeOn-time63%

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