Midway

$171+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Mar 9 — Mar 161
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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 February 7, 2026.

This Southwest deal was found by Cheapflights users on 2/3. 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 4/291:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Wed 5/610:20 am
MDW
-
HNL
1 stop12h 20m
Southwest
Deal found 2/3$342
This Southwest deal was found by Cheapflights users on 2/4. 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 3/28:05 am
HNL
-
MDW
1 stop12h 20m
Southwest
Mon 3/98:50 am
MDW
-
HNL
1 stop17h 20m
Southwest
Deal found 2/4$391
This Southwest deal was found by Cheapflights users on 2/6. 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.
Thu 5/71:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
-
HNL
1 stop11h 25m
Southwest
Deal found 2/6$413
This Delta deal was found by Cheapflights users on 2/4. 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 3/24:45 pm
HNL
-
MDW
1 stop12h 09m
Delta
Mon 3/99:30 am
MDW
-
HNL
2 stops16h 21m
Delta
Deal found 2/4$438
This Delta deal was found by Cheapflights users on 2/3. 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 4/304:10 pm
HNL
-
MDW
2 stops15h 33m
Delta
Wed 5/61:23 pm
MDW
-
HNL
2 stops13h 22m
Delta
Deal found 2/3$465
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:31 pm
HNL
-
MDW
2 stops14h 11m
Delta
Sun 5/109:22 am
MDW
-
HNL
2 stops16h 49m
Delta
Deal found 2/6$495
This Southwest deal was found by Cheapflights users on 2/3. 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 3/28:10 am
HNL
-
MDW
1 stop16h 55m
Southwest
Thu 3/59:30 pm
MDW
-
HNL
1 stop17h 30m
Southwest
Deal found 2/3$502
This Southwest deal was found by Cheapflights users on 2/4. 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 2/199:15 pm
LIH
-
MDW
2 stops17h 10m
Southwest
Mon 2/237:55 am
MDW
-
LIH
2 stops14h 20m
Southwest
Deal found 2/4$605
This Delta deal was found by Cheapflights users on 2/4. 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 pm
LIH
-
MDW
2 stops14h 56m
Delta
Mon 2/99:33 am
MDW
-
LIH
2 stops14h 21m
Delta
Deal found 2/4$619
This Delta deal was found by Cheapflights users on 2/5. 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 2/208:55 pm
KOA
-
MDW
2 stops15h 19m
Delta
Tue 2/249:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 2/5$639
This Southwest deal was found by Cheapflights users on 2/6. 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.
Mon 8/3110:00 am
OGG
-
MDW
1 stop14h 55m
Southwest
Tue 9/1510:15 am
MDW
-
OGG
1 stop10h 55m
Southwest
Deal found 2/6$654
This Southwest deal was found by Cheapflights users on 2/4. 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 2/57:05 pm
LIH
-
MDW
2 stops13h 25m
Southwest
Thu 3/1210:05 am
MDW
-
LIH
1 stop11h 05m
Southwest
Deal found 2/4$659

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 February 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$391
(Southwest)

One-way from

$171
(Southwest)

Popular in

July

Cheapest in

February

Average price

$471
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
From Hawaii to Chicago Midway
One-way flight from Hawaii to Chicago Midway
Highest demand for flights based on searches. 15% potential increase in price ($129 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 7, 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 4/29

1:00 pm-5:50 am

1 stop11h 50m

Chicago Midway

Wed 5/6

10:20 am-5:40 pm

1 stop12h 20m

$342

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Mon 3/9

8:50 am-9:10 pm

1 stop17h 20m

$391

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 5/7

1:00 pm-5:50 am

1 stop11h 50m

Chicago Midway

Sun 5/10

2:40 pm-9:05 pm

1 stop11h 25m

$413

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

5:15 pm-12:46 pm

2 stops15h 31m

Chicago Midway

Mon 3/9

9:30 am-8:51 pm

2 stops16h 21m

$443

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/30

4:10 pm-12:43 pm

2 stops15h 33m

Chicago Midway

Wed 5/6

1:23 pm-9:45 pm

2 stops13h 22m

$465

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/29

12:25 pm-8:51 am

2 stops15h 26m

Chicago Midway

Wed 5/6

9:31 am-9:45 pm

2 stops17h 14m

$492

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 2/19

9:15 pm-6:25 pm

2 stops17h 10m

Chicago Midway

Mon 2/23

7:55 am-6:15 pm

2 stops14h 20m

$605

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 2/20

8:55 pm-4:14 pm

2 stops15h 19m

Chicago Midway

Tue 2/24

9:34 am-7:39 pm

2 stops14h 05m

$639

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 3/5

9:20 pm-11:45 am

1 stop10h 25m

Chicago Midway

Thu 3/12

10:05 am-4:10 pm

1 stop11h 05m

$664

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 3/17

8:25 pm-1:45 pm

2 stops12h 20m

Chicago Midway

Mon 3/23

10:05 am-9:25 pm

2 stops16h 20m

$693

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

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 50m. 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?

  • 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.

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 February 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$783FlexibilityNo cancel feeOn-time63%

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