HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$224+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hawaii to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 17, 2025.

Round-trip from

$475
(Delta)

One-way from

$224
(Southwest)

Popular in

July

Cheapest in

November

Average price

$618
From Hawaii to Chicago Midway
Search Deals
One-way flight from Hawaii to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($110 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 11/174:45 pmHNL - MDW
1 stop12h 07mDelta
Mon 1/126:00 amMDW - HNL
1 stop13h 12mDelta
Deal found 9/15$475
This Delta deal was found by Cheapflights users on 9/17. 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.
Fri 10/314:50 pmHNL - MDW
1 stop10h 50mDelta
Wed 11/59:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 9/17$484
This Delta deal was found by Cheapflights users on 9/15. 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 11/174:45 pmHNL - MDW
1 stop12h 07mDelta
Mon 1/56:00 amMDW - HNL
1 stop13h 12mDelta
Deal found 9/15$511
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/149:10 pmHNL - MDW
1 stop10h 20mSouthwest
Tue 10/2111:55 amMDW - HNL
1 stop14h 05mSouthwest
Deal found 9/16$525
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 10/232:50 pmHNL - MDW
1 stop12h 50mDelta
Sun 10/269:35 amMDW - HNL
2 stops14h 34mDelta
Deal found 9/16$546
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/319:10 pmHNL - MDW
1 stop14h 40mSouthwest
Wed 11/58:55 pmMDW - HNL
1 stop18h 25mSouthwest
Deal found 9/17$556
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 9/228:30 pmKOA - MDW
1 stop11h 45mSouthwest
Mon 9/295:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 9/15$643
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 12/229:45 pmOGG - MDW
2 stops15h 34mDelta
Wed 12/316:00 amMDW - OGG
2 stops17h 28mDelta
Deal found 9/17$714
This Southwest deal was found by Cheapflights users on 9/17. 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.
Mon 12/229:35 pmOGG - MDW
1 stop10h 40mSouthwest
Wed 12/315:15 amMDW - OGG
1 stop11h 55mSouthwest
Deal found 9/17$778
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/158:30 pmKOA - MDW
2 stops12h 55mSouthwest
Fri 10/175:40 amMDW - KOA
1 stop12h 20mSouthwest
Deal found 9/15$798
This Delta deal was found by Cheapflights users on 9/16. 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.
Wed 10/19:30 pmKOA - MDW
2 stops15h 05mDelta
Sun 10/56:00 amMDW - KOA
2 stops18h 12mDelta
Deal found 9/16$800
This Delta deal was found by Cheapflights users on 9/16. 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.
Wed 10/18:32 pmLIH - MDW
2 stops16h 03mDelta
Sun 10/56:00 amMDW - LIH
2 stops18h 26mDelta
Deal found 9/16$806

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 September 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

Mon 11/17

4:45 pm-1:07 pm

2 stops16h 22m

Chicago Midway

Mon 1/12

6:00 am-3:12 pm

1 stop13h 12m

$480

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/31

4:50 pm-8:40 am

1 stop10h 50m

Chicago Midway

Wed 11/5

9:20 am-9:26 pm

2 stops16h 06m

$484

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 11/17

4:45 pm-8:52 am

1 stop12h 07m

Chicago Midway

Mon 1/5

6:00 am-3:12 pm

1 stop13h 12m

$511

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 10/14

9:10 pm-12:30 pm

1 stop10h 20m

Chicago Midway

Tue 10/21

11:55 am-9:00 pm

1 stop14h 05m

$525

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 10/23

2:50 pm-8:40 am

1 stop12h 50m

Chicago Midway

Sun 10/26

9:35 am-7:09 pm

2 stops14h 34m

$546

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/31

9:10 pm-4:50 pm

1 stop14h 40m

Chicago Midway

Wed 11/5

8:55 pm-11:20 am

1 stop18h 25m

$556

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/7

1:35 pm-8:50 am

2 stops15h 15m

Chicago Midway

Mon 1/12

6:00 am-3:12 pm

1 stop13h 12m

$602

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 9/22

8:30 pm-1:15 pm

1 stop11h 45m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$643

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 12/22

9:45 pm-5:19 pm

2 stops15h 34m

Chicago Midway

Wed 12/31

6:00 am-7:28 pm

2 stops17h 28m

$714

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 10/15

8:30 pm-2:25 pm

2 stops12h 55m

Chicago Midway

Fri 10/17

5:40 am-1:00 pm

1 stop12h 20m

$798

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 52 results
1
2
3
...
6

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 September 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.

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 11h 45m. The distance between Hawaii and Chicago Midway Airport is about 4213 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, 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hawaii to Midway

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
Boston to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
Baltimore to Midway flights
Newark to Midway flights
Santa Ana to O'Hare Intl flights
Atlanta to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Philadelphia to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Denver to Midway flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Burbank to O'Hare Intl flights
Raleigh to O'Hare Intl flights
San Jose to O'Hare Intl flights
Providence to O'Hare Intl flights
Miami to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Orlando to O'Hare Intl flights
Seattle to Midway flights
Cleveland to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Boston to Midway flights
Minneapolis to Midway flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Hartford to O'Hare Intl flights
Tampa to O'Hare Intl flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$617Average$808FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.