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$296+ Cheap flights from Midway (MDW) to Hawaii

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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Midway to Hawaii

Keep the following information in mind while searching for Midway to Hawaii flight deals. Data was last updated May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$524
(Delta)

One-way from

$296
(Southwest)

Popular in

December

Cheapest in

February

Average price

$722
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
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From Chicago Midway to Hawaii
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One-way flight from Chicago Midway to Hawaii
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Highest demand for flights based on searches. 3% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Midway to Hawaii

Cheapest flights from Midway to Hawaii
Explore the most affordable flight options available from Midway to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Sun 5/259:20 amMDW - HNL
2 stops16h 24mDelta
Mon 6/21:10 pmHNL - MDW
2 stops14h 26mDelta
Deal found 4/30$524
This Southwest deal was found by Cheapflights users on 4/30. 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 9/89:10 pmMDW - HNL
1 stop18h 10mSouthwest
Fri 9/1211:35 amHNL - MDW
2 stops12h 35mSouthwest
Deal found 4/30$529
This Southwest deal was found by Cheapflights users on 4/30. 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 9/26:10 amMDW - OGG
1 stop11h 15mSouthwest
Tue 9/98:30 pmOGG - MDW
1 stop12h 25mSouthwest
Deal found 4/30$550
This Delta deal was found by Cheapflights users on 4/30. 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 6/47:25 pmMDW - LIH
2 stops28h 35mDelta
Tue 6/108:35 pmLIH - MDW
2 stops17h 06mDelta
Deal found 4/30$561
This Delta deal was found by Cheapflights users on 4/30. 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.
Sun 9/219:20 amMDW - KOA
2 stops14h 20mDelta
Tue 9/308:40 pmKOA - MDW
2 stops16h 27mDelta
Deal found 4/30$566
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 8/96:00 amMDW - OGG
2 stops18h 33mDelta
Mon 9/812:05 pmOGG - MDW
2 stops15h 41mDelta
Deal found 4/30$641
This Southwest deal was found by Cheapflights users on 4/30. 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 5/209:25 pmMDW - KOA
2 stops19h 45mSouthwest
Wed 5/288:30 pmKOA - MDW
1 stop10h 15mSouthwest
Deal found 4/30$664
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 6/79:45 pmMDW - LIH
1 stop17h 35mSouthwest
Fri 6/136:15 amLIH - MDW
2 stops13h 15mSouthwest
Deal found 4/30$778
This Delta deal was found by Cheapflights users on 4/30. 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 6/106:00 amMDW - ITO
2 stops18h 09mDelta
Tue 6/1710:44 amITO - MDW
2 stops17h 57mDelta
Deal found 4/30$1,176
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 6/75:45 amMDW - ITO
2 stops17h 25mSouthwest
Fri 6/136:00 amITO - MDW
2 stops13h 30mSouthwest
Deal found 4/30$1,349

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Hawaii 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 May 1, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Hawaii that are best for you.

Fly from

Midway

Fly to

Hawaii

Route

Depart

Return

Price

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 5/25

9:20 am-8:44 pm

2 stops16h 24m

Honolulu

Mon 6/2

1:10 pm-8:36 am

2 stops14h 26m

$524

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 6/4

7:25 pm-7:00 pm

2 stops28h 35m

Lihue

Tue 6/10

8:35 pm-6:41 pm

2 stops17h 06m

$561

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 6/2

9:20 am-7:10 pm

2 stops14h 50m

Kona Intl

Tue 6/10

8:35 pm-6:41 pm

2 stops17h 06m

$592

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 5/20

9:25 pm-12:10 pm

2 stops19h 45m

Kona Intl

Wed 5/28

8:30 pm-11:45 am

1 stop10h 15m

$664

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 5/3

6:05 am-4:35 pm

2 stops15h 30m

Kahului

Mon 5/5

8:25 pm-11:45 am

1 stop10h 20m

$670

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 6/5

9:20 am-7:25 pm

2 stops15h 05m

Kahului

Wed 6/11

12:05 pm-8:44 am

2 stops15h 39m

$703

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 5/9

7:05 am-2:05 pm

1 stop12h 00m

Honolulu

Wed 5/14

11:15 am-5:20 am

1 stop13h 05m

$740

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sat 6/7

9:45 pm-10:20 am

1 stop17h 35m

Lihue

Fri 6/13

6:15 am-12:30 am

2 stops13h 15m

$778

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 6/10

6:00 am-8:08 pm

2 stops19h 08m

Hilo Intl

Tue 6/17

12:14 pm-8:41 am

2 stops15h 27m

$1,176

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 6/7

5:45 am-6:10 pm

2 stops17h 25m

Hilo Intl

Fri 6/13

6:00 am-12:30 am

2 stops13h 30m

$1,349

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 19 results
1
2

Best time to book a flight from Midway to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii from Midway 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 Chicago Midway Airport to Hawaii

What is the cheapest month to book a flight from Chicago Midway Airport to Hawaii?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $469). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $687). 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.

Rainfall in Hawaii by month

Plan your trip to Hawaii by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hawaii ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit Hawaii when rainfall is around 0.3 in.

Temperature in Hawaii by month

Plan your trip to Hawaii by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hawaii, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

Reviews of airlines servicing Hawaii

Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated May 1, 2025.
Read through reviews of airlines operating flights from Chicago to Hawaii, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Midway to Hawaii. 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 Chicago Midway Airport to Hawaii?

    While some choose either Chicago Midway - Kahului or Chicago Midway - Kona Intl, Chicago Midway - Honolulu is the most popular route from Chicago Midway Airport to Hawaii.

  • Can I find deals for flights from Midway to Hawaii that include hotel bookings?

    Yes. In addition to deals on Midway to Hawaii flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Hawaii?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Hawaii.

  • Can I find deals for business class flights from Midway to Hawaii?

    Yes. Cheapflights offers flight deals from Midway to Hawaii 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 Chicago Midway Airport to Hawaii?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $469). Flying from Chicago Midway Airport to Hawaii in June is currently the most expensive (average of $687). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Hawaii

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Midway to Hawaii

Discover the top 2 airlines that operate flights from Midway to Hawaii. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$431Average$856FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$479Average$795FlexibilityNo cancel feeOn-time63%

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