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$195+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Jan 24 — Jan 311
Sat 1/24
Sat 1/31
1 adult, Economy
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Cheap 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 December 25, 2025.

This Delta deal was found by Cheapflights users on 12/25. 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 12/316:00 amMDW - HNL
1 stop15h 00mDelta
Sun 1/185:15 pmHNL - MDW
1 stop11h 53mDelta
Deal found 12/25$661
This Delta deal was found by Cheapflights users on 12/25. 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 12/316:00 amMDW - HNL
1 stop13h 04mDelta
Tue 1/205:15 pmHNL - MDW
1 stop11h 53mDelta
Deal found 12/25$687
This Southwest deal was found by Cheapflights users on 12/25. 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 12/305:10 amMDW - OGG
1 stop12h 15mSouthwest
Wed 1/79:25 pmOGG - MDW
1 stop13h 20mSouthwest
Deal found 12/25$763
This Southwest deal was found by Cheapflights users on 12/24. 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 12/315:15 amMDW - KOA
1 stop12h 25mSouthwest
Mon 1/129:25 pmKOA - MDW
1 stop15h 10mSouthwest
Deal found 12/24$763
This Southwest deal was found by Cheapflights users on 12/22. 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 12/2311:35 amMDW - HNL
1 stop13h 25mSouthwest
Sun 12/289:55 pmHNL - MDW
1 stop12h 15mSouthwest
Deal found 12/22$818
This Southwest deal was found by Cheapflights users on 12/24. 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 12/265:10 amMDW - HNL
1 stop11h 55mSouthwest
Sun 12/288:00 amHNL - MDW
1 stop12h 55mSouthwest
Deal found 12/24$838
This Southwest deal was found by Cheapflights users on 12/24. 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 12/285:40 amMDW - OGG
2 stops13h 10mSouthwest
Tue 12/309:25 pmOGG - MDW
1 stop13h 35mSouthwest
Deal found 12/24$856
This Southwest deal was found by Cheapflights users on 12/24. 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 12/248:20 amMDW - HNL
1 stop16h 40mSouthwest
Sun 12/289:25 pmHNL - MDW
2 stops13h 10mSouthwest
Deal found 12/24$863
This Southwest deal was found by Cheapflights users on 12/24. 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 12/288:55 amMDW - HNL
2 stops16h 05mSouthwest
Tue 12/308:00 amHNL - MDW
1 stop12h 55mSouthwest
Deal found 12/24$878
This Southwest deal was found by Cheapflights users on 12/23. 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 12/245:25 amMDW - OGG
1 stop11h 40mSouthwest
Sun 12/287:00 pmOGG - MDW
2 stops13h 15mSouthwest
Deal found 12/23$878
This Southwest deal was found by Cheapflights users on 12/22. 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 12/2311:35 amMDW - HNL
2 stops13h 25mSouthwest
Sat 12/278:00 amHNL - MDW
1 stop12h 40mSouthwest
Deal found 12/22$888
This Southwest deal was found by Cheapflights users on 12/22. 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 12/235:10 amMDW - KOA
2 stops13h 35mSouthwest
Wed 12/319:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 12/22$888

Find flight deals from Midway to Hawaii

Keep the following information in mind while searching for Midway to Hawaii flight deals. Data was last updated December 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$429
(Delta)

One-way from

$195
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$900
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
Search Deals
From Chicago Midway to Hawaii
Search Deals
One-way flight from Chicago Midway to Hawaii
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 25, 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

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 3/2

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 3/5

5:10 pm-9:54 am

1 stop12h 44m

$431

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/3

9:33 am-7:54 pm

2 stops14h 21m

Lihue

Mon 2/9

10:39 pm-6:36 pm

2 stops15h 57m

$434

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 3/2

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Tue 3/10

4:00 pm-9:56 am

1 stop12h 56m

$443

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 3/2

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Mon 3/9

4:00 pm-12:29 pm

2 stops15h 29m

$449

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 1/20

9:50 am-7:55 pm

2 stops14h 05m

Lihue

Tue 2/17

10:40 pm-5:37 pm

2 stops14h 57m

$459

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 3/1

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 3/5

5:10 pm-9:54 am

1 stop12h 44m

$462

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Mon 2/9

5:10 pm-9:53 am

1 stop12h 43m

$467

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Tue 3/10

4:00 pm-12:29 pm

2 stops15h 29m

$473

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/5

5:10 pm-12:46 pm

2 stops15h 36m

$473

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 2/23

9:34 am-7:39 pm

2 stops14h 05m

Kona Intl

Mon 3/2

9:55 pm-5:37 pm

2 stops15h 42m

$474

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $310). Flying from Chicago Midway Airport to Hawaii in November is currently the most expensive (average of $840). 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.

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 December 25, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Hawaii, such as Southwest and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago Midway Airport to Hawaii?

    Delta and Southwest can get you from Chicago Midway Airport to Hawaii in just under 13h 37m. Your travel time can differ by up to 3h 38m. Airlines will cover a distance of 4184 mi. This flight may include one or multiple stops.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Hawaii (average of $310). Flying from Chicago Midway Airport to Hawaii in November is currently the most expensive (average of $840). 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 December 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$442Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$468Average$818FlexibilityNo cancel feeOn-time63%

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