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$211+ Cheap flights from Hawaii 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Hawaii to Midway

Cheapest flights from Hawaii to Midway
Explore the most affordable flight options available from Hawaii to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Southwest deal was found by Cheapflights users on 12/21. 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 12/239:15 pmKOA - MDW
1 stop12h 25mSouthwest
Mon 1/57:45 amMDW - KOA
2 stops17h 35mSouthwest
Deal found 12/21$743
This Delta deal was found by Cheapflights users on 12/21. 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 12/244:45 pmHNL - MDW
1 stop12h 04mDelta
Sun 1/119:32 amMDW - HNL
2 stops15h 56mDelta
Deal found 12/21$1,531
This Delta deal was found by Cheapflights users on 12/20. 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 12/2411:35 pmHNL - MDW
2 stops13h 44mDelta
Wed 12/319:29 amMDW - HNL
2 stops16h 31mDelta
Deal found 12/20$2,151

Find flight deals from Hawaii to Midway

Keep the following information in mind while searching for Hawaii to Midway flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$417
(Delta)

One-way from

$211
(Delta)

Popular in

July

Cheapest in

September

Average price

$741
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From Hawaii to Chicago Midway
Search Deals
One-way flight from Hawaii to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hawaii 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 December 23, 2025.
Use the filters below to find and compare flights from Hawaii to Chicago Midway Airport that are best for you.

Fly from

Hawaii

Fly to

Midway

Route

Depart

Return

Price

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 1/22

5:10 pm-9:53 am

1 stop12h 43m

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

$421

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 1/29

5:10 pm-9:53 am

1 stop12h 43m

Chicago Midway

Sun 2/8

6:00 am-3:37 pm

1 stop13h 37m

$421

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 1/18

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Sun 1/25

6:00 am-3:10 pm

1 stop13h 10m

$423

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 1/23

2:02 pm-8:52 am

2 stops14h 50m

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

$426

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 1/21

9:05 pm-5:55 pm

2 stops16h 50m

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

$426

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/29

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Wed 2/4

9:32 am-9:28 pm

2 stops15h 56m

$429

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 1/26

5:10 pm-9:53 am

1 stop12h 43m

Chicago Midway

Sun 2/8

6:00 am-3:37 pm

1 stop13h 37m

$433

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/22

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Thu 1/29

6:00 am-3:10 pm

1 stop13h 10m

$433

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/19

4:44 pm-8:52 am

1 stop12h 08m

Chicago Midway

Mon 1/26

6:00 am-3:10 pm

1 stop13h 10m

$433

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

1:55 pm-8:52 am

2 stops14h 57m

Chicago Midway

Wed 2/4

9:32 am-9:28 pm

2 stops15h 56m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 53 results
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Best time to book a flight from Hawaii to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Hawaii 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 Hawaii to Chicago Midway Airport

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

Find hourly flight availability from Hawaii 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 December 23, 2025.

One of the essential ways to save on airfare from Hawaii to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 39% on airfare.

Related info for your journey

Find useful and relevant information for your journey from Hawaii to Midway. 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 Hawaii to Chicago Midway Airport?

    Departing from Hawaii to Chicago Midway Airport will take you 11h 10m. The distance between Hawaii and Chicago Midway Airport is about 4213 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Hawaii to Chicago Midway Airport?

    Most travelers choose Honolulu - Chicago Midway, Lihue - Chicago Midway or Kahului - Chicago Midway when deciding on the best route from Hawaii to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hawaii 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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Alternative routes for Hawaii to Midway

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Top airline flying from Hawaii to Midway

Discover the top airline that operate flights from Hawaii 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$788FlexibilityNo cancel feeOn-time63%

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