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$210+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
jul. 16 — jul. 231
mié. 7/16
mié. 7/23
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 julio 11, 2025.

Round-trip from

$473
(Delta)

One-way from

$210
(Southwest)

Popular in

December

Cheapest in

February

Average price

$885
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. 3% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 11, 2025.

This Delta deal was found by Cheapflights users on 7/9. 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.
jue. 9/46:00 amMDW - KOA
2 stops18h 00mDelta
vie. 9/128:44 pmKOA - MDW
2 stops16h 51mDelta
Deal found 7/9$473
This Southwest deal was found by Cheapflights users on 7/8. 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.
jue. 11/67:45 amMDW - LIH
1 stop12h 30mSouthwest
jue. 11/139:10 pmLIH - MDW
1 stop11h 55mSouthwest
Deal found 7/8$486
This Southwest deal was found by Cheapflights users on 7/9. 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.
jue. 10/235:40 amMDW - KOA
1 stop12h 20mSouthwest
mar. 10/288:30 pmKOA - MDW
1 stop12h 35mSouthwest
Deal found 7/9$501
This Southwest deal was found by Cheapflights users on 7/9. 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.
dom. 11/27:45 amMDW - OGG
1 stop12h 25mSouthwest
dom. 11/169:25 pmOGG - MDW
1 stop11h 20mSouthwest
Deal found 7/9$569
This Delta deal was found by Cheapflights users on 7/7. 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.
mar. 12/25:25 pmMDW - HNL
2 stops22h 45mDelta
lun. 12/84:43 pmHNL - MDW
1 stop12h 02mDelta
Deal found 7/7$572
This Southwest deal was found by Cheapflights users on 7/9. 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.
dom. 10/2610:15 pmMDW - HNL
1 stop17h 05mSouthwest
vie. 10/319:10 pmHNL - MDW
2 stops14h 25mSouthwest
Deal found 7/9$574
This Delta deal was found by Cheapflights users on 7/7. 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.
vie. 10/316:00 amMDW - OGG
2 stops17h 23mDelta
mar. 11/410:10 pmOGG - MDW
2 stops15h 57mDelta
Deal found 7/7$593
This Trip.com deal was found by Cheapflights users on 7/8. 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.
dom. 8/176:20 amMDW - HNL
2 stops27h 40mMultiple Airlines
mar. 8/267:45 amHNL - MDW
2 stops25h 16mMultiple Airlines
Deal found 7/8$594
This Delta deal was found by Cheapflights users on 7/9. 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.
jue. 9/259:35 amMDW - LIH
2 stops14h 24mDelta
mar. 9/308:32 pmLIH - MDW
2 stops17h 03mDelta
Deal found 7/9$637
This Southwest deal was found by Cheapflights users on 7/9. 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.
mar. 10/217:10 amMDW - ITO
2 stops16h 00mSouthwest
mié. 10/226:55 pmITO - MDW
2 stops12h 40mSouthwest
Deal found 7/9$644
This Delta deal was found by Cheapflights users on 7/9. 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.
sáb. 9/271:43 pmMDW - ITO
2 stops35h 47mDelta
lun. 9/299:43 amITO - MDW
2 stops26h 52mDelta
Deal found 7/9$900

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 julio 11, 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

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

jue. 9/4

6:00 am-7:00 pm

2 stops18h 00m

Kona Intl

vie. 9/12

8:44 pm-6:35 pm

2 stops16h 51m

$473

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

vie. 9/5

7:55 am-6:10 pm

2 stops15h 15m

Lihue

mar. 9/9

8:40 pm-1:15 pm

1 stop11h 35m

$511

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

lun. 8/25

5:15 am-1:05 pm

2 stops12h 50m

Kona Intl

vie. 8/29

8:30 pm-11:55 am

1 stop10h 25m

$562

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mar. 8/19

6:10 am-4:30 pm

2 stops15h 20m

Kahului

mié. 8/27

8:30 pm-2:40 pm

2 stops13h 10m

$570

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

lun. 8/18

9:20 pm-10:20 am

1 stop18h 00m

Honolulu

lun. 8/25

9:00 pm-4:25 pm

2 stops14h 25m

$576

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

dom. 8/17

6:04 am-1:15 pm

1 stop12h 11m

Honolulu

mar. 8/26

4:09 pm-12:28 pm

2 stops15h 19m

$578

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

dom. 8/17

6:20 am-5:00 am

2 stops27h 40m

Honolulu

mar. 8/26

7:45 am-2:01 pm

2 stops25h 16m

$594

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

jue. 9/25

9:35 am-6:59 pm

2 stops14h 24m

Lihue

mar. 9/30

8:32 pm-6:35 pm

2 stops17h 03m

$637

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

mié. 8/20

6:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

jue. 8/28

6:55 pm-2:30 pm

2 stops14h 35m

$654

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

mar. 9/2

6:00 am-7:13 pm

2 stops18h 13m

Kahului

mar. 9/9

9:10 pm-6:37 pm

2 stops16h 27m

$736

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 21 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, 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.

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 julio 11, 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
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,951 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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

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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 julio 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$498Average$773FlexibilityNo cancel feeOn-time63%

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