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$227+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Oct 24 — Oct 311
Fri 10/24
Fri 10/31
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 September 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$455
(Delta)

One-way from

$227
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$670
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. 4% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 24, 2025.

This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:35 amMDW - LIH
2 stops14h 30mDelta
Tue 11/49:30 pmLIH - MDW
2 stops16h 13mDelta
Deal found 9/22$455
This Southwest deal was found by Cheapflights users on 9/24. 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 10/296:05 amMDW - OGG
1 stop11h 20mSouthwest
Tue 11/49:35 pmOGG - MDW
1 stop10h 00mSouthwest
Deal found 9/24$470
This Southwest deal was found by Cheapflights users on 9/22. 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 12/28:20 amMDW - HNL
1 stop16h 40mSouthwest
Wed 12/109:25 pmHNL - MDW
1 stop10h 10mSouthwest
Deal found 9/22$479
This Southwest deal was found by Cheapflights users on 9/22. 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.
Mon 10/2711:00 amMDW - HNL
1 stop15h 00mSouthwest
Mon 11/109:25 pmHNL - MDW
2 stops13h 30mSouthwest
Deal found 9/22$484
This Delta deal was found by Cheapflights users on 9/23. 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 12/109:59 amMDW - KOA
2 stops13h 27mDelta
Mon 3/210:55 pmKOA - MDW
2 stops15h 39mDelta
Deal found 9/23$486
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:59 amMDW - HNL
2 stops15h 49mDelta
Thu 12/112:27 pmHNL - MDW
2 stops14h 52mDelta
Deal found 9/22$490
This Delta deal was found by Cheapflights users on 9/23. 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 10/299:35 amMDW - KOA
2 stops14h 48mDelta
Tue 11/49:30 pmKOA - MDW
2 stops16h 13mDelta
Deal found 9/23$490
This Southwest deal was found by Cheapflights users on 9/24. 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 10/275:40 amMDW - KOA
1 stop12h 20mSouthwest
Fri 10/318:30 pmKOA - MDW
2 stops14h 55mSouthwest
Deal found 9/24$500
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:56 pmMDW - HNL
1 stop17h 53mMultiple Airlines
Fri 10/317:43 amHNL - MDW
2 stops26h 14mMultiple Airlines
Deal found 9/23$507
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:56 pmMDW - HNL
1 stop17h 53mMultiple Airlines
Sun 11/24:13 pmHNL - MDW
2 stops20h 39mMultiple Airlines
Deal found 9/23$508
This Southwest deal was found by Cheapflights users on 9/24. 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 12/85:15 amMDW - OGG
2 stops13h 35mSouthwest
Mon 12/159:25 pmOGG - MDW
1 stop13h 35mSouthwest
Deal found 9/24$508
This Southwest deal was found by Cheapflights users on 9/23. 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 10/296:05 amMDW - KOA
1 stop11h 55mSouthwest
Tue 11/49:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 9/23$508

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 September 24, 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

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 10/28

9:35 am-7:05 pm

2 stops14h 30m

Lihue

Tue 11/4

9:30 pm-5:43 pm

2 stops16h 13m

$455

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 10/29

6:05 am-12:25 pm

1 stop11h 20m

Kahului

Tue 11/4

9:35 pm-11:35 am

1 stop10h 00m

$470

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 1/25

6:00 am-3:12 pm

1 stop13h 12m

Honolulu

Sat 1/31

1:35 pm-8:50 am

2 stops15h 15m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 1/31

9:30 am-8:33 pm

2 stops15h 03m

Honolulu

Sun 2/8

4:45 pm-8:50 am

1 stop12h 05m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 1/21

6:00 am-3:12 pm

1 stop13h 12m

Honolulu

Tue 1/27

1:35 pm-8:50 am

2 stops15h 15m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 1/26

9:30 am-8:33 pm

2 stops15h 03m

Honolulu

Fri 1/30

5:00 pm-9:56 am

1 stop12h 56m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/3

8:10 am-3:45 pm

1 stop11h 35m

Honolulu

Fri 11/7

8:00 am-1:30 am

1 stop13h 30m

$479

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 1/13

9:30 am-8:33 pm

2 stops15h 03m

Honolulu

Tue 1/20

11:15 pm-6:08 pm

2 stops14h 53m

$482

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 10/25

9:20 am-8:26 pm

2 stops16h 06m

Honolulu

Fri 10/31

3:10 pm-9:45 am

1 stop13h 35m

$484

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 12/10

9:59 am-7:26 pm

2 stops13h 27m

Kona Intl

Mon 3/2

10:55 pm-6:34 pm

2 stops15h 39m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

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, 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 September 24, 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
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 11h 20m. Your travel time can differ by up to 3h 10m. 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, 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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Midway to Denver flights

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 September 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$762FlexibilityNo cancel feeOn-time63%

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