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Midway

$233+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$584
(Southwest)

One-way from

$233
(Southwest)

Popular in

June

Cheapest in

November

Average price

$875
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. 8% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 1, 2025.

This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:30 pmKOA - MDW
2 stops13h 55mSouthwest
Sun 10/125:15 amMDW - KOA
1 stop12h 15mSouthwest
Deal found 6/30$584
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/148:05 amHNL - MDW
1 stop11h 25mSouthwest
Mon 8/189:20 pmMDW - HNL
1 stop18h 00mSouthwest
Deal found 6/30$595
This Delta deal was found by Cheapflights users on 6/30. 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.
Mon 9/221:20 pmHNL - MDW
2 stops14h 33mDelta
Thu 10/236:00 amMDW - HNL
1 stop12h 30mDelta
Deal found 6/30$609
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 7/43:45 pmOGG - MDW
2 stops15h 40mSouthwest
Sat 7/196:10 amMDW - OGG
1 stop11h 45mSouthwest
Deal found 6/29$928
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/268:40 pmLIH - MDW
1 stop12h 35mSouthwest
Fri 8/87:40 amMDW - LIH
2 stops15h 30mSouthwest
Deal found 6/30$963
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 7/148:35 pmKOA - MDW
2 stops17h 05mDelta
Fri 7/189:25 amMDW - KOA
2 stops14h 35mDelta
Deal found 6/28$1,004
This Delta deal was found by Cheapflights users on 6/30. 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 7/168:58 pmOGG - MDW
2 stops15h 41mDelta
Mon 7/219:25 amMDW - OGG
2 stops15h 08mDelta
Deal found 6/30$1,407
This Delta deal was found by Cheapflights users on 6/30. 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 7/262:23 pmLIH - MDW
2 stops13h 22mDelta
Sun 8/36:00 amMDW - LIH
2 stops16h 32mDelta
Deal found 6/30$1,774

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 July 1, 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

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 10/4

8:30 pm-3:25 pm

2 stops13h 55m

Chicago Midway

Sun 10/12

5:15 am-12:30 pm

1 stop12h 15m

$584

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 8/14

8:05 am-12:30 am

1 stop11h 25m

Chicago Midway

Mon 8/18

9:20 pm-10:20 am

1 stop18h 00m

$595

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 9/22

1:20 pm-8:53 am

2 stops14h 33m

Chicago Midway

Thu 10/23

6:00 am-1:30 pm

1 stop12h 30m

$609

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 7/26

8:40 pm-2:15 pm

1 stop12h 35m

Chicago Midway

Fri 8/8

7:40 am-6:10 pm

2 stops15h 30m

$963

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 7/14

8:35 pm-6:40 pm

2 stops17h 05m

Chicago Midway

Fri 7/18

9:25 am-7:00 pm

2 stops14h 35m

$1,004

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 7/16

8:58 pm-5:39 pm

2 stops15h 41m

Chicago Midway

Mon 7/21

9:25 am-7:33 pm

2 stops15h 08m

$1,407

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 7/26

2:23 pm-8:45 am

2 stops13h 22m

Chicago Midway

Sun 8/3

6:00 am-5:32 pm

2 stops16h 32m

$1,774

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 9/10

8:30 pm-1:25 pm

1 stop11h 55m

$233

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 10/6

9:10 pm-6:07 pm

2 stops15h 57m

$236

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 9/29

8:32 pm-5:35 pm

2 stops16h 03m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 15 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 July 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Hawaii to Chicago Midway Airport as you normally would.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 1, 2025.
See what other customers who have flown with Southwest and Delta from Hawaii to Chicago Midway Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the most popular routes from Hawaii to Chicago Midway Airport?

    Most travelers choose Honolulu - Chicago Midway, Kona Intl - Chicago Midway or Kahului - 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.

  • What is the cheapest month to book a flight from Hawaii to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Hawaii to Chicago Midway Airport (average of $160). Flying from Hawaii to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hawaii?

Book flights to Hawaii if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 2 airlines flying from Hawaii to Midway

Discover the top 2 airlines 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$548FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$606Average$783FlexibilityNo cancel feeOn-time63%

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