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Midway

$186+ 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 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Hawaii to Midway

Best flights from Hawaii to Midway
Discover carefully curated flight deals from Hawaii to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This Delta deal was found by Cheapflights users on 12/31. 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 1/224:44 pmHNL - MDW
1 stop12h 08mDelta
Thu 1/296:00 amMDW - HNL
1 stop13h 10mDelta
Deal found 12/31$423
This Southwest deal was found by Cheapflights users on 1/1. 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 2/106:00 amKOA - MDW
2 stops12h 40mSouthwest
Wed 2/116:10 amMDW - KOA
1 stop11h 35mSouthwest
Deal found 1/1$790
This Delta deal was found by Cheapflights users on 1/1. 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 1/224:44 pmHNL - MDW
1 stop12h 08mDelta
Wed 2/46:00 amMDW - HNL
1 stop13h 10mDelta
Deal found 1/1$424
This Delta deal was found by Cheapflights users on 12/31. 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 1/304:44 pmHNL - MDW
1 stop12h 08mDelta
Fri 2/69:33 amMDW - HNL
2 stops15h 55mDelta
Deal found 12/31$428
This Delta deal was found by Cheapflights users on 12/31. 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 2/201:55 pmHNL - MDW
2 stops17h 08mDelta
Tue 3/36:00 amMDW - HNL
1 stop13h 11mDelta
Deal found 12/31$429
This Delta deal was found by Cheapflights users on 12/30. 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.
Sat 2/141:55 pmHNL - MDW
2 stops14h 59mDelta
Sat 2/216:00 amMDW - HNL
1 stop13h 11mDelta
Deal found 12/30$448
This Delta deal was found by Cheapflights users on 1/2. 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 1/2710:00 pmOGG - MDW
2 stops15h 29mDelta
Thu 2/56:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 1/2$487
This Delta deal was found by Cheapflights users on 12/31. 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 1/2010:00 pmOGG - MDW
2 stops16h 36mDelta
Mon 1/266:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 12/31$487
This Southwest deal was found by Cheapflights users on 12/31. 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.
Sat 2/77:00 pmKOA - MDW
2 stops13h 35mSouthwest
Sat 2/146:10 amMDW - KOA
2 stops19h 10mSouthwest
Deal found 12/31$859
This Delta deal was found by Cheapflights users on 12/31. 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 1/199:05 pmOGG - MDW
2 stops17h 31mDelta
Mon 1/266:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 12/31$504
This Delta deal was found by Cheapflights users on 1/1. 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 1/1$512
This Delta deal was found by Cheapflights users on 1/2. 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 2/1110:30 pmHNL - MDW
2 stops16h 10mDelta
Thu 2/196:00 amMDW - HNL
1 stop13h 11mDelta
Deal found 1/2$514
This Delta deal was found by Cheapflights users on 12/31. 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 12/31$515
This Delta deal was found by Cheapflights users on 12/31. 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 1/1410:00 pmOGG - MDW
2 stops16h 32mDelta
Wed 1/216:00 amMDW - OGG
2 stops17h 15mDelta
Deal found 12/31$678
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 1/149:31 pmLIH - MDW
2 stops17h 01mDelta
Thu 1/299:50 amMDW - LIH
2 stops14h 05mDelta
Deal found 12/30$688
This Delta deal was found by Cheapflights users on 12/31. 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 1/167:55 pmKOA - MDW
2 stops16h 34mDelta
Tue 1/206:00 amMDW - KOA
2 stops16h 47mDelta
Deal found 12/31$827
This Delta deal was found by Cheapflights users on 12/31. 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 1/155:10 pmOGG - MDW
1 stop13h 17mDelta
Mon 1/196:00 amMDW - OGG
1 stop13h 37mDelta
Deal found 12/31$891
This Delta deal was found by Cheapflights users on 1/2. 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.
Sat 1/175:10 pmOGG - MDW
1 stop13h 17mDelta
Wed 1/216:00 amMDW - OGG
2 stops17h 15mDelta
Deal found 1/2$923
This Delta deal was found by Cheapflights users on 12/31. 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 5/229:26 pmLIH - MDW
2 stops16h 05mDelta
Sun 5/319:30 amMDW - LIH
2 stops14h 50mDelta
Deal found 12/31$1,464

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 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$186
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$777
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. 11% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 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 2, 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 1/22

4:44 pm-8:52 am

1 stop12h 08m

Chicago Midway

Thu 1/29

6:00 am-3:10 pm

1 stop13h 10m

$423

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/22

4:44 pm-8:52 am

1 stop12h 08m

Chicago Midway

Wed 2/4

6:00 am-3:10 pm

1 stop13h 10m

$424

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 1/30

4:44 pm-8:52 am

1 stop12h 08m

Chicago Midway

Fri 2/6

9:33 am-9:28 pm

2 stops15h 55m

$428

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 2/20

1:55 pm-11:03 am

2 stops17h 08m

Chicago Midway

Tue 3/3

6:00 am-3:11 pm

1 stop13h 11m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sat 2/14

1:55 pm-8:54 am

2 stops14h 59m

Chicago Midway

Sat 2/21

6:00 am-3:11 pm

1 stop13h 11m

$448

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 1/27

10:00 pm-5:29 pm

2 stops15h 29m

Chicago Midway

Thu 2/5

6:00 am-3:37 pm

1 stop13h 37m

$487

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 1/20

10:00 pm-6:36 pm

2 stops16h 36m

Chicago Midway

Mon 1/26

6:00 am-3:37 pm

1 stop13h 37m

$487

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 1/19

9:05 pm-6:36 pm

2 stops17h 31m

Chicago Midway

Mon 1/26

6:00 am-3:37 pm

1 stop13h 37m

$504

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

$512

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 2/11

10:30 pm-6:40 pm

2 stops16h 10m

Chicago Midway

Thu 2/19

6:00 am-3:11 pm

1 stop13h 11m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 49 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 12h 08m. 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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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 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$581Average$788FlexibilityNo cancel feeOn-time63%

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