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$217+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$414
(Delta)

One-way from

$217
(Southwest)

Popular in

December

Cheapest in

February

Average price

$820
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 ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 12, 2025.

This Delta deal was found by Cheapflights users on 11/10. 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 12/76:00 amMDW - LIH
2 stops18h 10mDelta
Sun 12/149:50 pmLIH - MDW
2 stops16h 28mDelta
Deal found 11/10$414
This Delta deal was found by Cheapflights users on 11/11. 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 12/46:00 amMDW - OGG
1 stop13h 24mDelta
Mon 12/1510:00 pmOGG - MDW
2 stops16h 18mDelta
Deal found 11/11$437
This Delta deal was found by Cheapflights users on 11/11. 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 12/99:34 amMDW - OGG
2 stops14h 44mDelta
Mon 12/155:10 pmOGG - MDW
1 stop12h 44mDelta
Deal found 11/11$438
This Delta deal was found by Cheapflights users on 11/11. 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 - OGG
1 stop13h 24mDelta
Thu 1/155:10 pmOGG - MDW
1 stop13h 24mDelta
Deal found 11/11$456
This Delta deal was found by Cheapflights users on 11/11. 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 12/46:00 amMDW - OGG
1 stop13h 24mDelta
Thu 12/115:10 pmOGG - MDW
1 stop12h 44mDelta
Deal found 11/11$461
This Delta deal was found by Cheapflights users on 11/11. 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 12/119:59 amMDW - OGG
2 stops13h 03mDelta
Thu 12/185:10 pmOGG - MDW
1 stop12h 44mDelta
Deal found 11/11$466
This Delta deal was found by Cheapflights users on 11/11. 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.
Sat 12/66:00 amMDW - OGG
1 stop13h 24mDelta
Sun 12/1410:00 pmOGG - MDW
2 stops16h 18mDelta
Deal found 11/11$468
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:00 amMDW - OGG
1 stop13h 24mDelta
Tue 12/910:00 pmOGG - MDW
2 stops16h 18mDelta
Deal found 11/11$469
This Delta deal was found by Cheapflights users on 11/10. 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 12/47:02 pmMDW - OGG
2 stops29h 16mDelta
Fri 12/121:55 pmOGG - MDW
2 stops15h 24mDelta
Deal found 11/10$475
This Delta deal was found by Cheapflights users on 11/11. 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 - OGG
1 stop13h 24mDelta
Tue 1/131:53 pmOGG - MDW
2 stops15h 01mDelta
Deal found 11/11$487
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:00 amMDW - OGG
1 stop13h 24mDelta
Mon 12/155:10 pmOGG - MDW
1 stop12h 44mDelta
Deal found 11/11$492
This Delta deal was found by Cheapflights users on 11/10. 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 12/146:00 amMDW - OGG
1 stop13h 24mDelta
Thu 12/185:10 pmOGG - MDW
1 stop12h 44mDelta
Deal found 11/10$493

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 November 12, 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

Thu 12/4

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Sun 12/14

10:00 pm-6:18 pm

2 stops16h 18m

$437

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/5

6:45 am-3:37 pm

1 stop12h 52m

Kahului

Mon 1/12

10:00 pm-4:31 pm

2 stops14h 31m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/5

10:00 pm-5:32 pm

2 stops15h 32m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 12/9

6:00 am-8:18 pm

2 stops18h 18m

Kahului

Mon 12/15

5:10 pm-9:54 am

1 stop12h 44m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/1

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Thu 1/8

10:00 pm-4:31 pm

2 stops14h 31m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 12/8

9:34 am-8:18 pm

2 stops14h 44m

Kahului

Mon 12/15

5:10 pm-9:54 am

1 stop12h 44m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 1/21

6:00 am-7:15 pm

2 stops17h 15m

Kahului

Fri 1/30

10:00 pm-3:40 pm

2 stops13h 40m

$443

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:30 pm

1 stop13h 30m

Kahului

Tue 3/10

4:00 pm-9:56 am

1 stop12h 56m

$451

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 12/11

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Thu 12/18

5:10 pm-9:54 am

1 stop12h 44m

$461

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 12/5

9:34 am-8:29 pm

2 stops14h 55m

Honolulu

Tue 12/9

11:23 pm-6:18 pm

2 stops14h 55m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

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 $324). Flying from Chicago Midway Airport to Hawaii in July is currently the most expensive (average of $827). 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 November 12, 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
4,235 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

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
7.9
Good
8,008 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

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 12h 05m. Your travel time can differ by up to 1h 19m. Airlines will cover a distance of 4243 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 $324). Flying from Chicago Midway Airport to Hawaii in July is currently the most expensive (average of $827). 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$442Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$479Average$770FlexibilityNo cancel feeOn-time63%

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