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$277+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$524
(Delta)

One-way from

$277
(Delta)

Popular in

July

Cheapest in

October

Average price

$699
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. 9% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Delta deal was found by Cheapflights users on 4/17. 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.
Thu 5/81:20 pmHNL - MDW
2 stops14h 16mDelta
Sun 5/119:20 amMDW - HNL
2 stops16h 14mDelta
Deal found 4/17$524
This Delta deal was found by Cheapflights users on 4/16. 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 5/208:38 pmKOA - MDW
2 stops16h 07mDelta
Tue 6/39:20 amMDW - KOA
2 stops14h 50mDelta
Deal found 4/16$542
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:05 amHNL - MDW
1 stop11h 25mSouthwest
Sun 9/1410:25 pmMDW - HNL
1 stop16h 55mSouthwest
Deal found 4/17$603
This Delta deal was found by Cheapflights users on 4/17. 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 5/2112:00 pmOGG - MDW
2 stops15h 36mDelta
Tue 5/279:20 amMDW - OGG
2 stops15h 05mDelta
Deal found 4/17$661
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:30 pmKOA - MDW
1 stop13h 05mSouthwest
Wed 5/149:25 pmMDW - KOA
2 stops19h 45mSouthwest
Deal found 4/17$665
This Delta deal was found by Cheapflights users on 4/17. 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.
Thu 6/59:45 pmLIH - MDW
2 stops16h 00mDelta
Sun 6/229:24 amMDW - LIH
2 stops14h 46mDelta
Deal found 4/17$1,219

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 April 17, 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 5/8

1:20 pm-8:36 am

2 stops14h 16m

Chicago Midway

Sun 5/11

9:20 am-8:34 pm

2 stops16h 14m

$524

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 5/20

8:38 pm-5:45 pm

2 stops16h 07m

Chicago Midway

Tue 6/3

9:20 am-7:10 pm

2 stops14h 50m

$542

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 9/4

8:05 am-12:30 am

1 stop11h 25m

Chicago Midway

Sun 9/14

10:25 pm-10:20 am

1 stop16h 55m

$603

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 5/21

12:00 pm-8:36 am

2 stops15h 36m

Chicago Midway

Tue 5/27

9:20 am-7:25 pm

2 stops15h 05m

$661

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 5/8

8:30 pm-2:35 pm

1 stop13h 05m

Chicago Midway

Wed 5/14

9:25 pm-12:10 pm

2 stops19h 45m

$665

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 6/5

9:45 pm-6:45 pm

2 stops16h 00m

Chicago Midway

Sun 6/22

9:24 am-7:10 pm

2 stops14h 46m

$1,219

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 5/18

4:10 pm-12:28 pm

2 stops15h 18m

$277

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 5/23

12:10 pm-5:15 am

1 stop12h 05m

$291

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 6/10

8:35 pm-5:40 pm

2 stops16h 05m

$291

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 5/18

9:00 am-5:20 am

1 stop15h 20m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 14 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 April 17, 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 April 17, 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
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 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.

  • 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

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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$418Average$711FlexibilityNo cancel feeOn-time63%
DeltaCheapest$421Average$917FlexibilityNo cancel feeOn-timeN/A

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