HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$257+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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

Discover tips and strategies to find the most affordable flight options for your journey from Hawaii (USHI) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$444
(Delta)

One-way from

$257
(Delta)
From Hawaii to Chicago Midway
Search Deals
One-way flight from Hawaii to Chicago Midway
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 January 21, 2025.

This Delta deal was found by Cheapflights users on 1/21. 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 2/510:51 pmLIH - MDW
2 stops14h 52mDelta
Sun 2/99:33 amMDW - LIH
2 stops14h 36mDelta
Deal found 1/21$444
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/209:40 pmHNL - MDW
2 stops22h 37mMultiple Airlines
Wed 3/57:05 amMDW - HNL
2 stops19h 36mMultiple Airlines
Deal found 1/20$454
This Delta deal was found by Cheapflights users on 1/20. 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 2/136:40 pmHNL - MDW
2 stops14h 25mDelta
Mon 2/1710:19 amMDW - HNL
2 stops15h 37mDelta
Deal found 1/20$529
This Delta deal was found by Cheapflights users on 1/21. 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 2/52:25 pmOGG - MDW
2 stops14h 26mDelta
Sun 2/96:00 amMDW - OGG
1 stop15h 39mDelta
Deal found 1/21$608
This Delta deal was found by Cheapflights users on 1/21. 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 4/229:30 pmKOA - MDW
2 stops15h 34mDelta
Wed 4/309:30 amMDW - KOA
2 stops14h 09mDelta
Deal found 1/21$619
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/38:20 amHNL - MDW
1 stop10h 20mSouthwest
Fri 2/79:25 pmMDW - HNL
1 stop17h 55mSouthwest
Deal found 1/20$623
This Southwest deal was found by Cheapflights users on 1/21. 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 1/216:10 amKOA - MDW
2 stops12h 40mSouthwest
Sat 1/256:50 amMDW - KOA
1 stop13h 00mSouthwest
Deal found 1/21$632
This Southwest deal was found by Cheapflights users on 1/21. 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 2/56:00 amOGG - MDW
2 stops12h 50mSouthwest
Sun 2/98:40 pmMDW - OGG
2 stops21h 05mSouthwest
Deal found 1/21$679

Find flights from Hawaii to Midway within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

LihueChicago

LIH - MDW

LIHMDW

Lihue

Wed 2/5

10:51 pm-5:43 pm

2 stops14h 52m

Chicago Midway

Sun 2/9

9:33 am-8:09 pm

2 stops14h 36m

$444

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/20

9:40 pm-12:17 am

2 stops22h 37m

Chicago Midway

Wed 3/5

7:05 am-10:41 pm

2 stops19h 36m

$454

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/13

6:40 pm-1:05 pm

2 stops14h 25m

Chicago Midway

Mon 2/17

10:19 am-9:56 pm

2 stops15h 37m

$529

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 2/5

2:25 pm-8:51 am

2 stops14h 26m

Chicago Midway

Sun 2/9

6:00 am-5:39 pm

1 stop15h 39m

$608

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/22

9:30 pm-6:04 pm

2 stops15h 34m

Chicago Midway

Wed 4/30

9:30 am-6:39 pm

2 stops14h 09m

$619

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 2/3

8:20 am-10:40 pm

1 stop10h 20m

Chicago Midway

Fri 2/7

9:25 pm-11:20 am

1 stop17h 55m

$623

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 2/5

6:00 am-10:50 pm

2 stops12h 50m

Chicago Midway

Sun 2/9

8:40 pm-1:45 pm

2 stops21h 05m

$679

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 2/15

9:00 am-8:35 am

2 stops19h 35m

Chicago Midway

Sat 2/22

5:25 am-3:50 pm

1 stop14h 25m

$868

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 4/22

8:15 pm-5:03 pm

2 stops15h 48m

$257

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 2/9

4:50 pm-8:51 am

1 stop12h 01m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 16 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.

Travel insights for flights from Hawaii to Midway

Get recent, data-driven insights about flights from Hawaii to Midway including ideal travel times, pricing trends, and more.

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 January 21, 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 January 21, 2025.
Get a feel of what it's like to fly with Delta and Southwest 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
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Boston to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Los Angeles to O'Hare Intl flights
Orlando to O'Hare Intl flights
Newark to Midway flights
Seattle to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Los Angeles to Midway flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Atlanta to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
San Francisco to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Diego to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Tampa to O'Hare Intl flights
Minneapolis to Midway flights
Miami to O'Hare Intl flights
Reagan-National to Midway flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Philadelphia to Midway flights
Orlando to Midway flights
Hartford to O'Hare Intl flights
Burbank to O'Hare Intl flights
Denver to Midway flights
Hobby to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Detroit to O'Hare Intl flights
Portland to O'Hare Intl flights
San Jose to O'Hare Intl flights

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$926FlexibilityNo cancel feeOn-timeN/A
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.