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$241+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Apr 25 — May 21
Sat 4/25
Sat 5/2
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 March 26, 2026.

This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:30 am
MDW
-
LIH
2 stops14h 52m
Delta
Mon 11/1610:26 pm
LIH
-
MDW
2 stops16h 11m
Delta
Deal found 3/23$435
This Southwest deal was found by Cheapflights users on 3/25. 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.
Mon 8/3110:15 am
MDW
-
HNL
1 stop15h 55m
Southwest
Wed 9/98:15 am
HNL
-
MDW
1 stop15h 45m
Southwest
Deal found 3/25$475
This Southwest deal was found by Cheapflights users on 3/24. 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.
Tue 4/147:55 am
MDW
-
LIH
2 stops13h 15m
Southwest
Mon 4/208:10 pm
LIH
-
MDW
1 stop10h 50m
Southwest
Deal found 3/24$480
This Southwest deal was found by Cheapflights users on 3/24. 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.
Mon 8/176:40 am
MDW
-
LIH
1 stop10h 55m
Southwest
Mon 8/248:25 pm
LIH
-
MDW
1 stop12h 10m
Southwest
Deal found 3/24$484
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 9/222:00 pm
MDW
-
HNL
2 stops26h 57m
Delta
Tue 9/291:30 pm
HNL
-
MDW
2 stops14h 08m
Delta
Deal found 3/25$496
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 11/109:30 am
MDW
-
LIH
2 stops14h 52m
Delta
Sun 11/1510:45 pm
LIH
-
MDW
2 stops30h 04m
Delta
Deal found 3/25$496
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 9/152:00 pm
MDW
-
HNL
2 stops26h 57m
Delta
Thu 9/241:30 pm
HNL
-
MDW
2 stops14h 08m
Delta
Deal found 3/25$497
This Southwest deal was found by Cheapflights users on 3/22. 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 9/2212:00 pm
MDW
-
HNL
2 stops14h 20m
Southwest
Tue 9/298:55 pm
HNL
-
MDW
1 stop11h 40m
Southwest
Deal found 3/22$502
This Southwest deal was found by Cheapflights users on 3/22. 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 8/1810:20 am
MDW
-
HNL
1 stop15h 50m
Southwest
Mon 8/248:10 am
HNL
-
MDW
1 stop10h 35m
Southwest
Deal found 3/22$517
This Southwest deal was found by Cheapflights users on 3/22. 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.
Wed 4/226:10 am
MDW
-
LIH
2 stops15h 00m
Southwest
Tue 4/288:10 pm
LIH
-
MDW
1 stop10h 50m
Southwest
Deal found 3/22$520
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:45 pm
MDW
-
HNL
2 stops22h 12m
Delta
Fri 9/251:30 pm
HNL
-
MDW
2 stops14h 08m
Delta
Deal found 3/23$533
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:27 am
MDW
-
OGG
2 stops15h 05m
Delta
Wed 4/2912:30 pm
OGG
-
MDW
2 stops15h 16m
Delta
Deal found 3/23$538

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 March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$428
(Southwest)

One-way from

$241
(Southwest)

Popular in

June

Cheapest in

January

Average price

$767
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 ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Hawaii that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 8/18

6:50 am-4:10 pm

2 stops14h 20m

Lihue

Mon 8/24

8:25 pm-2:45 pm

2 stops13h 20m

$544

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 8/17

6:40 am-2:10 pm

2 stops12h 30m

Lihue

Mon 8/24

8:25 pm-2:45 pm

2 stops13h 20m

$556

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 4/13

7:50 am-4:35 pm

2 stops13h 45m

Kahului

Mon 4/20

8:25 pm-2:10 pm

2 stops12h 45m

$568

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 9/21

9:30 am-7:20 pm

2 stops14h 50m

Lihue

Tue 9/29

9:26 pm-6:31 pm

2 stops16h 05m

$579
Quickest round-trip

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 4/22

10:00 am-4:10 pm

1 stop11h 10m

Lihue

Tue 4/28

8:10 pm-12:00 pm

1 stop10h 50m

$579

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 4/24

5:25 am-2:10 pm

1 stop13h 45m

Kahului

Fri 5/1

8:25 pm-12:15 pm

1 stop10h 50m

$580

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 5/8

10:10 am-9:25 pm

2 stops16h 15m

Kona Intl

Wed 5/13

10:00 am-5:45 am

1 stop14h 45m

$594

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 5/9

6:55 am-2:50 pm

2 stops12h 55m

Kahului

Mon 5/18

8:55 pm-2:10 pm

2 stops12h 15m

$604

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 5/8

6:00 am-2:10 pm

2 stops13h 10m

Kahului

Fri 5/15

10:00 am-6:00 am

1 stop15h 00m

$608

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 5/5

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Tue 5/12

10:00 am-5:45 am

1 stop14h 45m

$630

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 57 resultsSorted by cheapest first
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6

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 $843). 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.

How much does it cost to fly round-trip from Chicago Midway Airport to Hawaii?

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 March 26, 2026.
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
4,333 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,336 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    Southwest and Delta can get you from Chicago Midway Airport to Hawaii in just under 14h 20m. Your travel time can differ by up to 30m. Airlines will cover a distance of 4289 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 $843). 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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$429Average$733FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$795FlexibilityNo cancel feeOn-time63%

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