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Midway

$265+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$426
(Southwest)

One-way from

$265
(Kiwi.com)

Popular in

July

Cheapest in

December

Average price

$606
From Honolulu to Chicago Midway
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One-way flight from Honolulu to Chicago Midway
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Highest demand for flights based on searches. 21% potential increase in price ($200 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 10/229:05 pmHNL - MDW
1 stop12h 35mSouthwest
Mon 10/279:25 pmMDW - HNL
1 stop17h 55mSouthwest
Deal found 9/12$426
This Southwest deal was found by Cheapflights users on 9/12. 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 10/149:00 pmHNL - MDW
1 stop12h 05mSouthwest
Tue 10/219:25 pmMDW - HNL
1 stop17h 55mSouthwest
Deal found 9/12$487
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/232:50 pmHNL - MDW
1 stop12h 50mDelta
Mon 10/279:35 amMDW - HNL
2 stops15h 51mDelta
Deal found 9/14$516
This Delta deal was found by Cheapflights users on 9/12. 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 10/221:15 pmHNL - MDW
2 stops14h 40mDelta
Mon 10/279:35 amMDW - HNL
2 stops14h 34mDelta
Deal found 9/12$521
This Delta deal was found by Cheapflights users on 9/12. 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 10/274:15 pmHNL - MDW
2 stops15h 13mDelta
Sat 11/19:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 9/12$528
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/279:05 pmHNL - MDW
1 stop10h 20mSouthwest
Mon 11/38:20 amMDW - HNL
1 stop16h 40mSouthwest
Deal found 9/14$534
This Southwest deal was found by Cheapflights users on 9/13. 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 10/279:10 pmHNL - MDW
1 stop10h 20mSouthwest
Sat 11/18:25 amMDW - HNL
1 stop16h 30mSouthwest
Deal found 9/13$543

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 September 15, 2025.
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 10/23

2:50 pm-8:40 am

1 stop12h 50m

Chicago Midway

Mon 10/27

9:35 am-8:26 pm

2 stops15h 51m

$516

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

3:10 pm-9:40 am

1 stop13h 30m

Chicago Midway

Sat 11/1

9:20 am-8:26 pm

2 stops16h 06m

$522

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 10/14

9:10 pm-3:10 pm

2 stops13h 00m

Chicago Midway

Tue 10/21

11:55 am-9:00 pm

1 stop14h 05m

$532

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

1:35 pm-8:50 am

2 stops15h 15m

Chicago Midway

Mon 1/12

6:00 am-3:12 pm

1 stop13h 12m

$532

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

9:05 pm-3:15 pm

2 stops13h 10m

Chicago Midway

Mon 11/3

8:20 am-9:00 pm

1 stop16h 40m

$539

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/27

9:10 pm-3:10 pm

2 stops13h 00m

Chicago Midway

Sat 11/1

8:25 am-7:55 pm

1 stop16h 30m

$548

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 3/1

9:35 pm-9:56 am

2 stops32h 21m

Chicago Midway

Tue 3/3

5:25 pm-9:50 pm

2 stops32h 25m

$598

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/31

10:51 pm-12:30 pm

2 stops32h 39m

$272

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 11/14

8:00 am-1:30 am

1 stop13h 30m

$272

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 10/6

3:02 pm-9:40 am

1 stop13h 38m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 18 results
1
2

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.

Cheapflights Insights

Everything you need to know about your flight from Honolulu to Chicago Midway Airport

What is the cheapest time of day to fly from HNL to MDW?

Find hourly flight availability from Honolulu to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s optimal to fly from Honolulu to Chicago Midway Airport at noon. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the afternoon.

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 September 15, 2025.
Read through reviews of airlines operating flights from Honolulu to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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 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. 2 airlines 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 $516, Delta can have you in Chicago Midway Airport from Honolulu in 12h 50m. The distance from Honolulu to Chicago Midway Airport is about 4243 mi. This flight may include one or multiple stops.

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

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $421. Another option worth looking into is Southwest, starting at $617 round trip. Delta is priced at 41% lower than the current average price of a flight leaving 3 months from now.

  • 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.

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

    Currently, April is the cheapest month in which you can book a flight from Honolulu to Chicago Midway Airport (average of $160). Flying from Honolulu to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

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

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Top 2 airlines flying from Honolulu to Midway

Discover the top 2 airlines 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$617Average$808FlexibilityNo cancel feeOn-time63%

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