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$223+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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 12/155:37 pmHNL - MDW
2 stops14h 57mDelta
Thu 1/16:00 amMDW - HNL
1 stop13h 04mDelta
Deal found 11/19$447
This Delta deal was found by Cheapflights users on 11/17. 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 12/2411:35 pmHNL - MDW
2 stops13h 44mDelta
Fri 1/26:00 amMDW - HNL
1 stop15h 25mDelta
Deal found 11/17$526
This Southwest deal was found by Cheapflights users on 11/18. 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 12/259:25 pmHNL - MDW
1 stop14h 15mSouthwest
Wed 12/318:20 amMDW - HNL
1 stop16h 40mSouthwest
Deal found 11/18$572
This Delta deal was found by Cheapflights users on 11/18. 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 11/252:19 pmHNL - MDW
2 stops14h 35mDelta
Tue 12/99:59 amMDW - HNL
2 stops15h 49mDelta
Deal found 11/18$600
This Delta deal was found by Cheapflights users on 11/20. 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 11/222:41 pmLIH - MDW
2 stops15h 11mDelta
Mon 11/246:00 amMDW - LIH
2 stops18h 30mDelta
Deal found 11/20$736
This Delta deal was found by Cheapflights users on 11/19. 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 12/48:59 pmOGG - MDW
2 stops17h 19mDelta
Mon 12/89:34 amMDW - OGG
2 stops14h 44mDelta
Deal found 11/19$827
This Delta deal was found by Cheapflights users on 11/20. 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 11/272:37 pmOGG - MDW
2 stops14h 24mDelta
Sun 11/306:00 amMDW - OGG
1 stop13h 28mDelta
Deal found 11/20$1,140

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$223
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$712
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From Hawaii to Chicago Midway
Search Deals
One-way flight from Hawaii to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($85 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 November 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 November 20, 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 1/15

1:55 pm-8:52 am

2 stops14h 57m

Chicago Midway

Mon 1/19

6:00 am-3:11 pm

1 stop13h 11m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/12

4:44 pm-8:52 am

1 stop12h 08m

Chicago Midway

Sun 1/18

9:32 am-9:28 pm

2 stops15h 56m

$429

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/15

5:37 pm-12:34 pm

2 stops14h 57m

Chicago Midway

Thu 1/1

6:00 am-3:04 pm

1 stop13h 04m

$447

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 1/12

9:00 pm-2:45 pm

1 stop13h 45m

Chicago Midway

Sun 1/18

8:15 am-9:00 pm

1 stop16h 45m

$450

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 12/24

11:35 pm-5:19 pm

2 stops13h 44m

Chicago Midway

Fri 1/2

6:00 am-5:25 pm

1 stop15h 25m

$526

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 3/2

5:00 pm-9:58 am

1 stop12h 58m

Chicago Midway

Wed 3/4

12:46 pm-12:30 pm

2 stops27h 44m

$529

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 1/16

5:10 pm-10:32 am

1 stop13h 22m

Chicago Midway

Tue 1/20

9:32 am-7:15 pm

2 stops13h 43m

$625

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 4/28

12:45 pm-8:38 am

2 stops14h 53m

Chicago Midway

Thu 4/30

6:45 pm-11:01 am

2 stops21h 16m

$652

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 12/4

8:59 pm-6:18 pm

2 stops17h 19m

Chicago Midway

Mon 12/8

9:34 am-8:18 pm

2 stops14h 44m

$827

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 3/2

11:50 am-1:09 pm

2 stops21h 19m

Chicago Midway

Wed 3/4

7:17 pm-8:28 pm

2 stops29h 11m

$862

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 40 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 November 20, 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 14h 57m. The distance between Hawaii and Chicago Midway Airport is about 4243 mi.

  • 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$516Average$778FlexibilityNo cancel feeOn-time63%

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