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$212+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$554
(Delta)

One-way from

$212
(Southwest)

Popular in

July

Cheapest in

October

Average price

$644
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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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. 7% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 8/2112:35 pmHNL - MDW
2 stops15h 01mDelta
Tue 8/269:30 amMDW - HNL
2 stops14h 42mDelta
Deal found 4/30$554
This Southwest deal was found by Cheapflights users on 4/30. 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 9/48:10 amHNL - MDW
1 stop10h 15mSouthwest
Thu 9/119:10 pmMDW - HNL
1 stop18h 10mSouthwest
Deal found 4/30$563
This Delta deal was found by Cheapflights users on 4/30. 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 5/219:39 pmKOA - MDW
2 stops15h 06mDelta
Tue 6/39:20 amMDW - KOA
2 stops14h 50mDelta
Deal found 4/30$592
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 9/168:30 pmKOA - MDW
1 stop14h 15mSouthwest
Fri 10/37:45 amMDW - KOA
2 stops15h 25mSouthwest
Deal found 4/30$723
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/159:30 pmOGG - MDW
2 stops16h 15mDelta
Mon 5/199:20 amMDW - OGG
2 stops15h 05mDelta
Deal found 4/30$822
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/59:45 pmLIH - MDW
2 stops16h 00mDelta
Sun 6/226:00 amMDW - LIH
2 stops17h 30mDelta
Deal found 4/30$986

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 May 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

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 8/21

12:35 pm-8:36 am

2 stops15h 01m

Chicago Midway

Tue 8/26

9:30 am-7:12 pm

2 stops14h 42m

$554

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/4

8:10 am-11:25 pm

1 stop10h 15m

Chicago Midway

Thu 9/11

9:10 pm-10:20 am

1 stop18h 10m

$563

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 5/21

9:39 pm-5:45 pm

2 stops15h 06m

Chicago Midway

Tue 6/3

9:20 am-7:10 pm

2 stops14h 50m

$592

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

8:30 pm-3:45 pm

1 stop14h 15m

Chicago Midway

Fri 10/3

7:45 am-6:10 pm

2 stops15h 25m

$723

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 5/15

9:30 pm-6:45 pm

2 stops16h 15m

Chicago Midway

Mon 5/19

9:20 am-7:25 pm

2 stops15h 05m

$822

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 6/5

9:45 pm-6:45 pm

2 stops16h 00m

Chicago Midway

Sun 6/22

6:00 am-6:30 pm

2 stops17h 30m

$986

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 8/26

8:40 pm-3:45 pm

1 stop14h 05m

$212

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 8/26

9:45 pm-6:28 pm

2 stops15h 43m

$237

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 6/6

1:10 pm-8:36 am

2 stops14h 26m

$251

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 5/20

9:30 pm-5:45 pm

2 stops15h 15m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 15 results
1
2

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 May 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Hawaii to Chicago by reading reviews from past customers. 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
4,293 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Hawaii to Midway

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$418Average$753FlexibilityNo cancel feeOn-time63%
DeltaCheapest$421Average$911FlexibilityNo cancel feeOn-timeN/A

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