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$245+ Cheap flights from Midway (MDW) to Honolulu (HNL)

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
1 adult, Economy
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Cheap flight deals from Midway to Honolulu

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Honolulu (HNL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 11, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$426
(Southwest)

One-way from

$245
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$429
Provider with most accurate pricing for Chicago Midway-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Honolulu flights.
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From Chicago Midway to Honolulu
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One-way flight from Chicago Midway to Honolulu
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Highest demand for flights based on searches. 12% potential increase in price ($106 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 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 Honolulu

Cheapest flights from Midway to Honolulu
Explore the most affordable flight options available from Midway to Honolulu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 11, 2026.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/17:55 amMDW - HNL
1 stop12h 35mSouthwest
Wed 2/412:30 pmHNL - MDW
2 stops12h 35mSouthwest
Deal found 1/8$426
This Southwest deal was found by Cheapflights users on 1/10. 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 3/27:55 amMDW - HNL
1 stop12h 35mSouthwest
Mon 3/99:05 pmHNL - MDW
2 stops13h 45mSouthwest
Deal found 1/10$428
This Southwest deal was found by Cheapflights users on 1/9. 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 2/68:00 amMDW - HNL
1 stop17h 00mSouthwest
Fri 2/138:05 amHNL - MDW
2 stops12h 45mSouthwest
Deal found 1/9$429
This Delta deal was found by Cheapflights users on 1/9. 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.
Sun 2/229:34 amMDW - HNL
2 stops15h 54mDelta
Thu 2/265:15 pmHNL - MDW
1 stop11h 51mDelta
Deal found 1/9$430
This Southwest deal was found by Cheapflights users on 1/9. 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 3/48:15 amMDW - HNL
1 stop16h 45mSouthwest
Wed 3/118:15 amHNL - MDW
1 stop15h 45mSouthwest
Deal found 1/9$431
This Southwest deal was found by Cheapflights users on 1/9. 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 4/175:10 amMDW - HNL
1 stop11h 25mSouthwest
Wed 4/291:00 pmHNL - MDW
1 stop17h 05mSouthwest
Deal found 1/9$432
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.
Wed 2/259:50 amMDW - HNL
2 stops16h 04mDelta
Tue 3/1012:59 pmHNL - MDW
2 stops14h 54mDelta
Deal found 1/8$435
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/237:25 pmMDW - HNL
1 stop19h 50mMultiple Airlines
Thu 2/2611:50 amHNL - MDW
2 stops31h 51mMultiple Airlines
Deal found 1/10$438
This Southwest deal was found by Cheapflights users on 1/9. 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 2/188:55 pmMDW - HNL
1 stop18h 20mSouthwest
Wed 2/259:55 pmHNL - MDW
1 stop16h 25mSouthwest
Deal found 1/9$441
This Kiwi.com deal was found by Cheapflights users on 1/9. 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 2/237:25 pmMDW - HNL
1 stop19h 50mMultiple Airlines
Thu 3/512:55 pmHNL - MDW
2 stops53h 46mMultiple Airlines
Deal found 1/9$443
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:10 amMDW - HNL
1 stop13h 00mSouthwest
Mon 2/99:30 pmHNL - MDW
2 stops13h 15mSouthwest
Deal found 1/8$447

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Honolulu 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 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Honolulu that are best for you.

Fly from

Midway

Fly to

Honolulu

Route

Depart

Return

Price

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 1/27

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Tue 2/3

1:17 pm-8:52 am

2 stops15h 35m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/26

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Mon 3/2

5:15 pm-9:06 am

1 stop11h 51m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/9

9:35 am-8:53 pm

2 stops16h 18m

Honolulu

Wed 4/15

4:05 pm-8:46 am

1 stop11h 41m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 2/25

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Wed 3/4

5:15 pm-9:06 am

1 stop11h 51m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 2/20

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Tue 3/24

3:46 pm-8:53 am

1 stop12h 07m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/9

9:35 am-8:53 pm

2 stops16h 18m

Honolulu

Thu 4/16

3:10 pm-8:47 am

1 stop12h 37m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Sun 2/8

1:55 pm-8:52 am

2 stops14h 57m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 3/1

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

Sun 2/8

9:33 am-9:28 pm

2 stops15h 55m

Honolulu

Sun 3/8

4:20 pm-8:50 am

1 stop11h 30m

$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

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to Honolulu

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Honolulu in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Honolulu flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Honolulu flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Honolulu flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Honolulu flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Honolulu flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Honolulu

Have a flexible travel schedule? Discover the best time to fly to Honolulu 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 Honolulu

What is the cheapest month to book a flight from Chicago Midway Airport to Honolulu?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $310). Flying from Chicago Midway Airport to Honolulu 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 Honolulu

Get insights into the airlines that provide service to Honolulu. 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 Honolulu. Reviews last updated January 11, 2026.
Read reviews from past customers who have flown Southwest and Delta from Chicago Midway Airport to Honolulu. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
8,033 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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 Honolulu. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Honolulu from Chicago Midway?

    Honolulu (HNL), located 4.4 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Honolulu. 2 airlines have flights to Honolulu from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Honolulu should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Honolulu?

    Departing from Chicago Midway Airport to Honolulu will take you 13h 10m. Chicago Midway Airport and Honolulu are separated by a distance of 4243 mi.

  • What are the cheapest airlines flying from Chicago Midway Airport to Honolulu round-trip?

    Delta, at $429, was found to be the cheapest airline from Chicago Midway Airport to Honolulu. An alternate airline flying to your destination would be Southwest. Delta is currently priced 42% below the average price you’ll pay for this route.

  • Can I find deals for flights from Midway to Honolulu that include hotel bookings?

    Yes. In addition to deals on Midway to Honolulu flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Honolulu?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Honolulu.

  • Can I find deals for business class flights from Midway to Honolulu?

    Yes. Cheapflights offers flight deals from Midway to Honolulu 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 Honolulu?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $310). Flying from Chicago Midway Airport to Honolulu 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

Traveling to a place near Honolulu?

Book flights to Honolulu if you plan to visit one of these locations
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Top 2 airlines flying from Midway to Honolulu

Discover the top 2 airlines that operate flights from Midway to Honolulu. 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 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$429Average$614FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$598Average$768FlexibilityNo cancel feeOn-time63%

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