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Midway

$218+ Cheap flights from Honolulu (HNL) to Midway (MDW)

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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
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Cheap flight deals from Honolulu to Midway

Cheapest flights from Honolulu to Midway
Explore the most affordable flight options available from Honolulu to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 31, 2026.

This Southwest deal was found by Cheapflights users on 1/29. 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.
Thu 2/198:05 am
HNL
-
MDW
1 stop12h 20m
Southwest
Wed 2/258:25 am
MDW
-
HNL
1 stop12h 05m
Southwest
Deal found 1/29$342
This Southwest deal was found by Cheapflights users on 1/29. 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.
Thu 2/269:55 pm
HNL
-
MDW
2 stops11h 45m
Southwest
Sun 3/110:15 pm
MDW
-
HNL
1 stop17h 00m
Southwest
Deal found 1/29$348
This Southwest deal was found by Cheapflights users on 1/30. 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 3/18:05 am
HNL
-
MDW
1 stop12h 30m
Southwest
Wed 3/48:15 am
MDW
-
HNL
1 stop16h 45m
Southwest
Deal found 1/30$422
This Delta deal was found by Cheapflights users on 1/29. 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 4/293:15 pm
HNL
-
MDW
1 stop12h 32m
Delta
Sun 5/36:00 am
MDW
-
HNL
1 stop12h 45m
Delta
Deal found 1/29$424
This Southwest deal was found by Cheapflights users on 1/28. 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 4/291:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Sat 5/210:15 am
MDW
-
HNL
2 stops15h 50m
Southwest
Deal found 1/28$496
This Southwest deal was found by Cheapflights users on 1/28. 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 3/28:05 am
HNL
-
MDW
1 stop12h 20m
Southwest
Tue 3/179:20 pm
MDW
-
HNL
1 stop17h 40m
Southwest
Deal found 1/28$521
This Delta deal was found by Cheapflights users on 1/29. 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 2/195:15 pm
HNL
-
MDW
2 stops15h 31m
Delta
Wed 2/259:34 am
MDW
-
HNL
2 stops16h 20m
Delta
Deal found 1/29$523
This Southwest deal was found by Cheapflights users on 1/29. 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 2/188:10 am
HNL
-
MDW
1 stop10h 30m
Southwest
Wed 2/256:10 am
MDW
-
HNL
1 stop13h 00m
Southwest
Deal found 1/29$528

Find flight deals from Honolulu to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Honolulu (HNL) to Midway (MDW). 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 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Southwest)

One-way from

$218
(Delta)

Popular in

July

Cheapest in

February

Average price

$686
Provider with most accurate pricing for Honolulu-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago Midway flights.
Search Deals
From Honolulu to Chicago Midway
Search Deals
One-way flight from Honolulu to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($115 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 January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Honolulu to Midway 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 31, 2026.
Use the filters below to find and compare flights from Honolulu to Chicago Midway Airport that are best for you.

Fly from

Honolulu

Fly to

Midway

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/19

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Wed 2/25

8:25 am-4:30 pm

1 stop12h 05m

$342

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/26

9:55 pm-6:20 pm

1 stop16h 25m

Chicago Midway

Sun 3/1

10:50 am-9:00 pm

1 stop14h 10m

$342

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 3/1

8:05 am-12:35 am

1 stop12h 30m

Chicago Midway

Wed 3/4

8:15 am-9:00 pm

1 stop16h 45m

$422

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/29

3:15 pm-8:47 am

1 stop12h 32m

Chicago Midway

Sun 5/3

6:00 am-1:45 pm

1 stop12h 45m

$424

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/29

1:00 pm-5:50 am

1 stop11h 50m

Chicago Midway

Sat 5/2

10:15 am-9:05 pm

2 stops15h 50m

$496

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Tue 3/17

9:20 pm-10:00 am

1 stop17h 40m

$521

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/19

5:15 pm-12:46 pm

2 stops15h 31m

Chicago Midway

Wed 2/25

9:34 am-9:54 pm

2 stops16h 20m

$523

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 3/17

11:50 am-5:55 am

1 stop13h 05m

$251

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/18

3:46 pm-8:53 am

1 stop12h 07m

$251

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 3/17

12:35 pm-8:53 am

2 stops15h 18m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 18 results
1
2

Compare providers for flights from Honolulu to Midway

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 Honolulu to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Honolulu-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Honolulu-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Honolulu-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Honolulu-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Honolulu-Chicago Midway Airport 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 Honolulu to Midway

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated January 31, 2026.
Read through reviews of airlines operating flights from Honolulu to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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 Honolulu to Midway. 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 from for flights from Honolulu to Chicago Midway?

    Honolulu (HNL), located 4.4 mi from the city center, is the airport you fly out of when you book flights from Honolulu to Chicago Midway. 1 airline have flights from Honolulu to Chicago Midway on a regular basis. Booking flights from Honolulu to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    For as low as $342, Southwest can have you in Chicago Midway Airport from Honolulu in 12h 20m. The distance from Honolulu to Chicago Midway Airport is about 4243 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Honolulu to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $581.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Honolulu to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Honolulu to Midway

Discover the top airline that operate flights from Honolulu to Midway. 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 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$783FlexibilityNo cancel feeOn-time63%

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