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$251+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — MDW
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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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 December 22, 2024.

Round-trip from

$427
(Delta)

One-way from

$251
(Delta)
From Hawaii to Chicago Midway
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One-way flight from Hawaii to Chicago Midway
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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 December 22, 2024.

This Southwest deal was found by Cheapflights users on 12/21. 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 12/258:40 amHNL - MDW
1 stop10h 45mSouthwest
Wed 1/18:45 pmMDW - HNL
2 stops20h 10mSouthwest
Deal found 12/21$777
This Southwest deal was found by Cheapflights users on 12/21. 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.
Mon 12/237:30 amKOA - MDW
1 stop12h 15mSouthwest
Wed 12/258:35 pmMDW - KOA
2 stops20h 15mSouthwest
Deal found 12/21$975
This Delta deal was found by Cheapflights users on 12/21. 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 12/316:39 pmHNL - MDW
1 stop12h 29mDelta
Thu 1/96:00 amMDW - HNL
1 stop12h 56mDelta
Deal found 12/21$987

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 2/14

4:50 pm-8:51 am

1 stop12h 01m

Chicago Midway

Tue 2/18

10:19 am-9:56 pm

2 stops15h 37m

$427

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/23

8:20 am-10:40 pm

1 stop10h 20m

Chicago Midway

Wed 2/5

8:35 pm-11:20 am

1 stop18h 45m

$582

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 1/24

9:00 pm-4:12 pm

2 stops15h 12m

Chicago Midway

Mon 1/27

6:00 am-8:55 pm

2 stops18h 55m

$688

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 5/20

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Tue 6/3

6:00 am-12:55 pm

1 stop11h 55m

$722

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/15

4:50 pm-8:54 am

1 stop12h 04m

$251

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 1/16

9:00 am-11:00 pm

1 stop10h 00m

$274

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 1/22

2:25 pm-9:39 am

2 stops15h 14m

$276

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 1/31

9:30 pm-4:12 pm

2 stops14h 42m

$279

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sat 5/10

11:15 am-5:20 am

1 stop13h 05m

$316

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 1/22

8:00 am-10:50 pm

1 stop10h 50m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 11 results
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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 December 22, 2024.

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 December 22, 2024.
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
4,804 reviews

Food

7.2

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

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
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

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
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

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 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

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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 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$926FlexibilityNo cancel feeOn-timeN/A
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