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Midway

$191+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

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.
Thu 2/269:55 pm
HNL
-
MDW
1 stop16h 25m
Southwest
Sun 3/110:50 am
MDW
-
HNL
1 stop14h 10m
Southwest
Deal found 1/28$342
This Southwest deal was found by Cheapflights users on 1/26. 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
1 stop16h 25m
Southwest
Thu 3/59:30 pm
MDW
-
HNL
1 stop17h 30m
Southwest
Deal found 1/26$360
This Delta 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 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 1/28$424
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/261:55 pm
HNL
-
MDW
2 stops14h 59m
Delta
Sun 3/19:34 am
MDW
-
HNL
2 stops16h 20m
Delta
Deal found 1/28$435
This Southwest deal was found by Cheapflights users on 1/26. 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 5/1111:55 am
HNL
-
MDW
2 stops12h 05m
Southwest
Mon 5/189:45 pm
MDW
-
HNL
1 stop17h 05m
Southwest
Deal found 1/26$456
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:55 pm
KOA
-
MDW
2 stops14h 42m
Delta
Wed 2/259:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 1/28$462
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 2/189:00 pm
HNL
-
MDW
1 stop11h 10m
Southwest
Sun 2/2210:15 pm
MDW
-
HNL
1 stop17h 00m
Southwest
Deal found 1/28$483
This Delta deal was found by Cheapflights users on 1/27. 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 2/251:55 pm
HNL
-
MDW
2 stops15h 11m
Delta
Wed 3/46:00 am
MDW
-
HNL
1 stop13h 11m
Delta
Deal found 1/27$488
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:55 pm
KOA
-
MDW
2 stops15h 45m
Delta
Sun 2/229:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 1/28$555
This Southwest deal was found by Cheapflights users on 1/27. 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 2/129:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Tue 2/177:55 am
MDW
-
KOA
2 stops17h 25m
Southwest
Deal found 1/27$568
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 2/187:00 pm
KOA
-
MDW
2 stops13h 10m
Southwest
Wed 2/256:10 am
MDW
-
KOA
1 stop11h 35m
Southwest
Deal found 1/28$592
This Southwest deal was found by Cheapflights users on 1/27. 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 2/129:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Mon 2/165:00 am
MDW
-
KOA
1 stop12h 45m
Southwest
Deal found 1/27$640

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Southwest)

One-way from

$191
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$686
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. 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 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 29, 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

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

Thu 2/26

9:55 pm-6:20 pm

1 stop16h 25m

Chicago Midway

Thu 3/5

9:30 pm-11:00 am

1 stop17h 30m

$360

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

Mon 5/11

11:55 am-5:00 am

2 stops12h 05m

Chicago Midway

Mon 5/18

9:45 pm-9:50 am

1 stop17h 05m

$456

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 2/18

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

Wed 2/25

9:34 am-7:39 pm

2 stops14h 05m

$462

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 2/25

1:55 pm-9:06 am

2 stops15h 11m

Chicago Midway

Wed 3/4

6:00 am-3:11 pm

1 stop13h 11m

$488

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 2/18

9:00 pm-12:10 pm

1 stop11h 10m

Chicago Midway

Sun 2/22

10:50 am-9:00 pm

1 stop14h 10m

$493

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

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 2/18

10:55 pm-6:40 pm

2 stops15h 45m

Chicago Midway

Sun 2/22

9:34 am-7:39 pm

2 stops14h 05m

$555

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 2/12

9:25 pm-3:00 pm

1 stop13h 35m

Chicago Midway

Tue 2/17

7:55 am-9:20 pm

2 stops17h 25m

$568

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 47 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 14h 42m. 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, Kona Intl - 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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
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Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Los Angeles to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
LaGuardia to Midway flights
Reagan-National to Midway flights
Atlanta to Midway flights
Raleigh to O'Hare Intl flights
Baltimore to Midway flights
Cleveland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Diego to O'Hare Intl flights
Philadelphia to Midway flights
Orlando to O'Hare Intl flights
Denver to Midway flights
Tampa to O'Hare Intl flights
Hartford to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Love Field to O'Hare Intl flights
San Francisco to Midway flights
Sacramento to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to Midway flights
San Antonio to O'Hare Intl flights
Kansas City to O'Hare Intl flights
Miami to O'Hare Intl flights
Detroit 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$783FlexibilityNo cancel feeOn-time63%

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