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$230+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:00 pmHNL - MDW
1 stop12h 54mDelta
Wed 12/109:59 amMDW - HNL
2 stops15h 49mDelta
Deal found 10/30$542
This Delta deal was found by Cheapflights users on 10/29. 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 11/1210:55 pmLIH - MDW
2 stops15h 13mDelta
Tue 11/189:34 amMDW - LIH
2 stops14h 30mDelta
Deal found 10/29$548
This Southwest deal was found by Cheapflights users on 10/29. 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 11/127:05 pmLIH - MDW
2 stops13h 35mSouthwest
Tue 11/185:15 amMDW - LIH
1 stop12h 00mSouthwest
Deal found 10/29$588
This Southwest deal was found by Cheapflights users on 10/30. 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.
Thu 12/49:00 pmHNL - MDW
1 stop11h 45mSouthwest
Wed 12/108:10 amMDW - HNL
1 stop11h 35mSouthwest
Deal found 10/30$597
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 11/1410:55 pmLIH - MDW
2 stops15h 13mDelta
Tue 11/189:34 amMDW - LIH
2 stops14h 30mDelta
Deal found 10/29$629
This Delta deal was found by Cheapflights users on 10/29. 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 12/182:45 pmHNL - MDW
2 stops14h 34mDelta
Sun 1/49:29 amMDW - HNL
2 stops16h 31mDelta
Deal found 10/29$673
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1611:04 amHNL - MDW
1 stop25h 48mMultiple Airlines
Mon 12/812:18 pmMDW - HNL
2 stops26h 42mMultiple Airlines
Deal found 10/30$707
This Southwest deal was found by Cheapflights users on 10/29. 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 11/129:55 pmHNL - MDW
1 stop10h 45mSouthwest
Sun 11/167:55 amMDW - HNL
1 stop12h 30mSouthwest
Deal found 10/29$713
This Southwest deal was found by Cheapflights users on 10/30. 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.
Wed 11/58:00 amHNL - MDW
1 stop10h 55mSouthwest
Thu 11/67:55 amMDW - HNL
1 stop12h 30mSouthwest
Deal found 10/30$717
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:06 pmHNL - MDW
2 stops26h 06mMultiple Airlines
Sun 12/213:01 pmMDW - HNL
1 stop23h 54mMultiple Airlines
Deal found 10/29$719
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:30 pmKOA - MDW
2 stops17h 38mDelta
Tue 11/189:41 amMDW - KOA
2 stops13h 44mDelta
Deal found 10/30$768
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/239:55 pmKOA - MDW
2 stops15h 24mDelta
Mon 12/299:29 amMDW - KOA
2 stops14h 13mDelta
Deal found 10/29$1,269

Cheap flight deals from Hawaii to Midway

Keep the following information in mind while searching for Hawaii to Midway flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$542
(Delta)

One-way from

$230
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$553
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
Search Deals
From Hawaii to Chicago Midway
Search Deals
One-way flight from Hawaii to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 12/4

5:00 pm-9:54 am

1 stop12h 54m

Chicago Midway

Wed 12/10

9:59 am-9:48 pm

2 stops15h 49m

$542

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

10:23 am-11:20 am

1 stop20h 57m

Chicago Midway

Mon 1/12

9:07 pm-8:51 pm

2 stops27h 44m

$545

LihueChicago

LIH - MDW

LIHMDW

Lihue

Wed 11/12

10:55 pm-6:08 pm

2 stops15h 13m

Chicago Midway

Tue 11/18

9:34 am-8:04 pm

2 stops14h 30m

$548

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

10:23 am-11:20 am

1 stop20h 57m

Chicago Midway

Sun 1/11

8:26 pm-2:07 pm

2 stops21h 41m

$559

LihueChicago

LIH - MDW

LIHMDW

Lihue

Wed 11/12

7:05 pm-12:40 pm

2 stops13h 35m

Chicago Midway

Tue 11/18

5:15 am-1:15 pm

1 stop12h 00m

$588

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 12/4

9:00 pm-12:45 pm

1 stop11h 45m

Chicago Midway

Wed 12/10

8:10 am-3:45 pm

1 stop11h 35m

$597

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

9:35 pm-5:34 pm

2 stops15h 59m

Chicago Midway

Sun 1/11

9:34 am-9:28 pm

2 stops15h 54m

$624

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

9:35 pm-5:34 pm

2 stops15h 59m

Chicago Midway

Mon 1/12

9:34 am-9:28 pm

2 stops15h 54m

$624

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 11/14

10:55 pm-6:08 pm

2 stops15h 13m

Chicago Midway

Tue 11/18

9:34 am-8:04 pm

2 stops14h 30m

$629

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 4/28

12:45 pm-1:07 pm

2 stops19h 22m

Chicago Midway

Thu 4/30

1:05 pm-11:01 am

2 stops26h 56m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 43 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 October 30, 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 12h 54m. The distance between Hawaii and Chicago Midway Airport is about 4243 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, Kahului - Chicago Midway or Lihue - 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Hawaii to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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John F Kennedy Intl to Midway flights
Baltimore to Midway flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Boston to Midway flights
Providence to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Columbus to O'Hare Intl flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$516Average$778FlexibilityNo cancel feeOn-time63%

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