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$283+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$455
(Delta)

One-way from

$283
(Southwest)

Popular in

June

Cheapest in

October

Average price

$736
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. 13% potential increase in price ($112 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 February 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 February 20, 2025.

This Delta deal was found by Cheapflights users on 2/19. 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 3/65:25 pmOGG - MDW
1 stop12h 47mDelta
Mon 3/106:00 amMDW - OGG
1 stop15h 41mDelta
Deal found 2/19$455
This Delta deal was found by Cheapflights users on 2/19. 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 3/55:05 pmHNL - MDW
1 stop13h 07mDelta
Mon 3/106:00 amMDW - HNL
1 stop13h 19mDelta
Deal found 2/19$455
This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/310:35 pmHNL - MDW
1 stop25h 48mMultiple Airlines
Tue 4/88:50 pmMDW - HNL
1 stop13h 10mMultiple Airlines
Deal found 2/19$541
This Southwest deal was found by Cheapflights users on 2/18. 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 4/711:20 amOGG - MDW
1 stop13h 00mSouthwest
Sun 4/205:55 amMDW - OGG
1 stop12h 05mSouthwest
Deal found 2/18$569
This Southwest deal was found by Cheapflights users on 2/19. 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 5/811:15 amHNL - MDW
1 stop13h 05mSouthwest
Sun 5/1110:20 pmMDW - HNL
1 stop16h 45mSouthwest
Deal found 2/19$585
This Delta deal was found by Cheapflights users on 2/19. 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 4/228:20 pmKOA - MDW
2 stops17h 00mDelta
Wed 4/309:20 amMDW - KOA
2 stops14h 22mDelta
Deal found 2/19$716
This Southwest deal was found by Cheapflights users on 2/19. 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 5/198:30 pmKOA - MDW
2 stops12h 30mSouthwest
Fri 5/238:00 amMDW - KOA
2 stops18h 20mSouthwest
Deal found 2/19$895

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 February 20, 2025.

Fly from

Hawaii

Fly to

Midway

Route

Depart

Return

Price

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 3/6

5:25 pm-10:12 am

1 stop12h 47m

Chicago Midway

Mon 3/10

6:00 am-4:41 pm

1 stop15h 41m

$455

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/5

5:05 pm-10:12 am

1 stop13h 07m

Chicago Midway

Mon 3/10

6:00 am-2:19 pm

1 stop13h 19m

$455

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/3

10:35 pm-5:23 am

1 stop25h 48m

Chicago Midway

Tue 4/8

8:50 pm-5:00 am

1 stop13h 10m

$541

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 4/7

11:20 am-5:20 am

1 stop13h 00m

Chicago Midway

Sun 4/20

5:55 am-1:00 pm

1 stop12h 05m

$569

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 5/8

11:15 am-5:20 am

1 stop13h 05m

Chicago Midway

Sun 5/11

10:20 pm-10:05 am

1 stop16h 45m

$585

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/22

8:20 pm-6:20 pm

2 stops17h 00m

Chicago Midway

Wed 4/30

9:20 am-6:42 pm

2 stops14h 22m

$716

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 5/19

8:30 pm-2:00 pm

2 stops12h 30m

Chicago Midway

Fri 5/23

8:00 am-9:20 pm

2 stops18h 20m

$895

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 5/7

11:15 am-5:20 am

1 stop13h 05m

$283

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 5/5

4:05 pm-12:35 pm

2 stops15h 30m

$288

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 5/9

12:45 pm-8:39 am

2 stops14h 54m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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
New Buffalo
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$418Average$617FlexibilityNo cancel feeOn-time63%
DeltaCheapest$421Average$926FlexibilityNo cancel feeOn-timeN/A
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