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$228+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$466
(Delta)

One-way from

$233
(Delta)

Popular in

December

Cheapest in

February

Average price

$588
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. 2% potential increase in price ($16 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 February 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 February 20, 2025.

This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 3/510:19 amMDW - HNL
2 stops15h 37mDelta
Sun 3/910:31 pmHNL - MDW
2 stops14h 47mDelta
Deal found 2/20$466
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 3/65:45 amMDW - HNL
1 stop13h 50mSouthwest
Sun 3/91:55 pmHNL - MDW
1 stop16h 15mSouthwest
Deal found 2/19$485
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 3/126:00 amMDW - OGG
1 stop15h 41mDelta
Wed 3/198:57 pmOGG - MDW
2 stops16h 21mDelta
Deal found 2/20$497
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 3/265:40 amMDW - OGG
1 stop16h 00mSouthwest
Wed 4/211:20 amOGG - MDW
1 stop13h 00mSouthwest
Deal found 2/20$505
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.
Sun 8/245:15 amMDW - LIH
1 stop12h 35mSouthwest
Thu 8/2810:00 amLIH - MDW
2 stops14h 10mSouthwest
Deal found 2/19$608
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 4/99:23 amMDW - LIH
2 stops14h 31mDelta
Mon 4/1410:00 pmLIH - MDW
2 stops14h 19mDelta
Deal found 2/20$614
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/68:50 pmMDW - OGG
1 stop18h 25mMultiple Airlines
Sun 4/1310:40 amOGG - MDW
2 stops24h 01mMultiple Airlines
Deal found 2/20$625
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 9/236:10 amMDW - KOA
1 stop11h 00mSouthwest
Sun 9/288:30 pmKOA - MDW
1 stop10h 15mSouthwest
Deal found 2/20$643
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/68:50 pmMDW - HNL
1 stop13h 10mMultiple Airlines
Sun 4/1310:35 pmHNL - MDW
1 stop25h 48mMultiple Airlines
Deal found 2/20$665
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.
Fri 5/168:00 amMDW - ITO
2 stops18h 40mSouthwest
Mon 5/196:55 pmITO - MDW
2 stops13h 05mSouthwest
Deal found 2/19$704
This Delta deal was found by Cheapflights users on 2/20. 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 4/310:25 amMDW - KOA
2 stops13h 17mDelta
Thu 4/108:20 pmKOA - MDW
2 stops41h 13mDelta
Deal found 2/20$713
This Delta deal was found by Cheapflights users on 2/20. 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.
Sun 4/66:00 amMDW - ITO
2 stops17h 00mDelta
Sun 4/139:30 amITO - MDW
2 stops18h 10mDelta
Deal found 2/20$1,066

Find flights from Midway to Hawaii within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Hawaii

Route

Depart

Return

Price

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 3/3

5:30 am-3:35 pm

1 stop14h 05m

Lihue

Mon 3/10

8:00 am-11:30 pm

1 stop10h 30m

$463

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 3/5

10:19 am-9:56 pm

2 stops15h 37m

Honolulu

Sun 3/9

10:31 pm-6:18 pm

2 stops14h 47m

$466

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 3/6

5:45 am-3:35 pm

1 stop13h 50m

Honolulu

Sun 3/9

1:55 pm-11:10 am

1 stop16h 15m

$485

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 3/12

6:00 am-4:41 pm

1 stop15h 41m

Kahului

Wed 3/19

8:57 pm-6:18 pm

2 stops16h 21m

$497

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 3/26

5:40 am-4:40 pm

1 stop16h 00m

Kahului

Wed 4/2

11:20 am-5:20 am

1 stop13h 00m

$505

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 4/9

9:23 am-6:54 pm

2 stops14h 31m

Lihue

Mon 4/14

10:00 pm-5:19 pm

2 stops14h 19m

$614

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 4/6

8:50 pm-10:15 am

1 stop18h 25m

Kahului

Sun 4/13

10:40 am-3:41 pm

2 stops24h 01m

$625

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 4/6

8:50 pm-5:00 am

1 stop13h 10m

Honolulu

Sun 4/13

10:35 pm-5:23 am

1 stop25h 48m

$665

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 2/25

9:40 am-8:20 pm

2 stops14h 40m

Kona Intl

Mon 3/3

9:00 am-12:05 am

1 stop11h 05m

$668

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 5/16

8:00 am-9:40 pm

2 stops18h 40m

Hilo Intl

Mon 5/19

6:55 pm-1:00 pm

2 stops13h 05m

$704

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 22 results
1
2
3

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.

Travel insights for flights from Midway to Hawaii

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

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.

What is the cheapest time of day to fly from MDW to HI?

Find hourly flight availability from Midway to Hawaii. 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 Chicago Midway Airport to Hawaii as you normally would.

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 February 20, 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
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

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 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 - Lihue, 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

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$431Average$878FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$479Average$747FlexibilityNo cancel feeOn-time63%
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