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$180+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$360
(Southwest)

One-way from

$180
(Southwest)

Popular in

July

Cheapest in

February

Average price

$721
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From Hawaii to Chicago Midway
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One-way flight from Hawaii to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 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 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 January 8, 2026.

This Southwest deal was found by Cheapflights users on 1/6. 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 3/181:50 pmHNL - MDW
1 stop11h 05mSouthwest
Tue 4/710:05 amMDW - HNL
1 stop15h 55mSouthwest
Deal found 1/6$360
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 4/112:35 pmHNL - MDW
2 stops15h 18mDelta
Wed 4/89:30 amMDW - HNL
2 stops16h 22mDelta
Deal found 1/8$409
This Southwest deal was found by Cheapflights users on 1/7. 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 3/159:25 pmHNL - MDW
1 stop15h 40mSouthwest
Tue 3/3110:30 amMDW - HNL
1 stop12h 10mSouthwest
Deal found 1/7$422
This Delta deal was found by Cheapflights users on 1/7. 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 2/69:20 pmLIH - MDW
2 stops14h 56mDelta
Mon 2/99:33 amMDW - LIH
2 stops14h 21mDelta
Deal found 1/7$480
This Southwest deal was found by Cheapflights users on 1/6. 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 2/18:05 amHNL - MDW
1 stop12h 20mSouthwest
Sat 2/78:25 amMDW - HNL
1 stop16h 35mSouthwest
Deal found 1/6$508
This Delta deal was found by Cheapflights users on 1/7. 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 1/229:31 pmLIH - MDW
2 stops16h 24mDelta
Mon 1/269:33 amMDW - LIH
2 stops14h 22mDelta
Deal found 1/7$510
This Southwest deal was found by Cheapflights users on 1/7. 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 4/298:25 pmOGG - MDW
1 stop10h 30mSouthwest
Mon 5/46:35 amMDW - OGG
1 stop11h 00mSouthwest
Deal found 1/7$516
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.
Fri 2/209:35 pmHNL - MDW
2 stops14h 39mDelta
Tue 3/36:00 amMDW - HNL
1 stop13h 11mDelta
Deal found 1/8$520
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 2/1810:55 pmKOA - MDW
2 stops14h 42mDelta
Sun 2/229:34 amMDW - KOA
2 stops14h 05mDelta
Deal found 1/8$535
This Delta deal was found by Cheapflights users on 1/7. 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 4/78:55 pmKOA - MDW
2 stops16h 45mDelta
Sun 4/127:20 pmMDW - KOA
2 stops27h 23mDelta
Deal found 1/7$536
This Delta deal was found by Cheapflights users on 1/7. 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 1/229:05 pmOGG - MDW
2 stops17h 31mDelta
Mon 1/266:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 1/7$629
This Delta deal was found by Cheapflights users on 1/7. 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 1/227:55 pmKOA - MDW
2 stops12h 51mDelta
Mon 1/266:00 amMDW - KOA
2 stops16h 47mDelta
Deal found 1/7$653

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 January 8, 2026.
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

Wed 3/18

1:50 pm-5:55 am

1 stop11h 05m

Chicago Midway

Tue 4/7

10:05 am-9:00 pm

1 stop15h 55m

$360

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/1

3:30 pm-8:53 am

1 stop12h 23m

Chicago Midway

Wed 4/8

9:30 am-8:52 pm

2 stops16h 22m

$417

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 3/15

9:25 pm-6:05 pm

1 stop15h 40m

Chicago Midway

Tue 3/31

10:30 am-5:40 pm

1 stop12h 10m

$422

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 2/6

9:20 pm-4:16 pm

2 stops14h 56m

Chicago Midway

Mon 2/9

9:33 am-7:54 pm

2 stops14h 21m

$480

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 2/1

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Sat 2/7

8:25 am-9:00 pm

1 stop16h 35m

$508

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 1/22

9:31 pm-5:55 pm

2 stops16h 24m

Chicago Midway

Mon 1/26

9:33 am-7:55 pm

2 stops14h 22m

$510

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 4/29

8:25 pm-11:55 am

1 stop10h 30m

Chicago Midway

Mon 5/4

6:35 am-12:35 pm

1 stop11h 00m

$516

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 2/20

9:35 pm-4:14 pm

2 stops14h 39m

Chicago Midway

Tue 3/3

6:00 am-3:11 pm

1 stop13h 11m

$520

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 2/18

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

Sun 2/22

9:34 am-7:39 pm

2 stops14h 05m

$535

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/7

8:55 pm-6:40 pm

2 stops16h 45m

Chicago Midway

Sun 4/12

7:20 pm-5:43 pm

2 stops27h 23m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 50 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
No data available for this route at this time. Please check back soon.

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 05m. 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, Lihue - Chicago Midway or Kona Intl - 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

See prices for flight routes from nearby airports that may be better suited for you.
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Los Angeles to Midway flights
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Dulles Intl to Midway flights
Love Field to O'Hare Intl flights
Newark to Midway flights
Charlotte to O'Hare Intl flights
Seattle to O'Hare Intl flights
LaGuardia to Midway flights
Minneapolis to O'Hare Intl flights
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Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Minneapolis to Midway flights
Orlando to O'Hare Intl flights
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Baltimore to Midway flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Midway flights
Denver to Midway flights
Detroit to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to Midway flights
Love Field to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Miami to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Francisco to Midway flights
San Jose to O'Hare Intl flights
Columbus to O'Hare Intl flights
Hobby to Midway 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$783FlexibilityNo cancel feeOn-time63%

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