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$303+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$600
(Southwest)

One-way from

$303
(Delta)

Popular in

December

Cheapest in

February

Average price

$940
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. 3% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Southwest deal was found by Cheapflights users on 6/16. 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 9/31:35 pmMDW - HNL
1 stop12h 25mSouthwest
Mon 9/811:35 amHNL - MDW
2 stops12h 35mSouthwest
Deal found 6/16$600
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 10/44:25 pmMDW - HNL
2 stops32h 25mDelta
Tue 10/289:38 pmHNL - MDW
2 stops15h 29mDelta
Deal found 6/14$603

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 June 16, 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

Wed 9/3

1:35 pm-9:00 pm

1 stop12h 25m

Honolulu

Mon 9/8

11:35 am-5:10 am

2 stops12h 35m

$600

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 8/18

6:04 am-1:15 pm

1 stop12h 11m

Honolulu

Mon 8/25

3:00 pm-8:35 am

1 stop12h 35m

$605

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 9/4

9:30 am-7:05 pm

2 stops14h 35m

$303

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 9/4

12:10 pm-9:00 pm

1 stop13h 50m

$317

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 6/28

9:12 pm-9:50 pm

2 stops29h 38m

$639

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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.

Rainfall in O'ahu by month

Plan your trip to O'ahu by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in O'ahu ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit O'ahu when rainfall is around 0.3 in.

Temperature in O'ahu by month

Plan your trip to O'ahu by taking into account the average temperature totals by month.

If weather is an important factor for your trip to O'ahu, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

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 June 16, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Chicago to O'ahu by reading reviews from past customers. 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
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$559Average$764FlexibilityNo cancel feeOn-time63%

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