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$233+ Cheap flights from Midway (MDW) to Honolulu (HNL)

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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midway to Honolulu

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Honolulu (HNL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Round-trip from

$465
(Southwest)

One-way from

$233
(Southwest)

Popular in

July

Cheapest in

February

Average price

$770
From Chicago Midway to Honolulu
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One-way flight from Chicago Midway to Honolulu
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Highest demand for flights based on searches. 12% potential increase in price ($109 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Midway to Honolulu

Cheapest flights from Midway to Honolulu
Explore the most affordable flight options available from Midway to Honolulu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/17. 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 11/48:20 amMDW - HNL
1 stop16h 40mSouthwest
Thu 12/49:25 pmHNL - MDW
1 stop10h 10mSouthwest
Deal found 8/17$465
This Delta deal was found by Cheapflights users on 8/17. 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 11/279:30 amMDW - HNL
2 stops16h 15mDelta
Fri 12/54:43 pmHNL - MDW
1 stop12h 02mDelta
Deal found 8/17$470
This Delta deal was found by Cheapflights users on 8/18. 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 10/259:20 amMDW - HNL
2 stops16h 06mDelta
Fri 10/314:50 pmHNL - MDW
1 stop10h 50mDelta
Deal found 8/18$471
This Delta deal was found by Cheapflights users on 8/18. 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 11/49:35 amMDW - HNL
2 stops15h 51mDelta
Tue 11/1111:15 pmHNL - MDW
2 stops15h 21mDelta
Deal found 8/18$476
This Southwest deal was found by Cheapflights users on 8/16. 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 9/297:40 amMDW - HNL
1 stop18h 20mSouthwest
Wed 10/158:05 amHNL - MDW
1 stop11h 20mSouthwest
Deal found 8/16$479
This Southwest deal was found by Cheapflights users on 8/16. 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 11/118:20 amMDW - HNL
1 stop16h 40mSouthwest
Tue 11/258:00 amHNL - MDW
1 stop12h 55mSouthwest
Deal found 8/16$493
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sat 10/258:30 amMDW - HNL
1 stop12h 35mSouthwest
Fri 10/318:05 amHNL - MDW
1 stop10h 30mSouthwest
Deal found 8/18$494
This Delta deal was found by Cheapflights users on 8/17. 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 9/96:00 amMDW - HNL
1 stop12h 15mDelta
Mon 9/154:10 pmHNL - MDW
2 stops15h 18mDelta
Deal found 8/17$499
This Delta deal was found by Cheapflights users on 8/17. 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 9/239:20 amMDW - HNL
2 stops16h 15mDelta
Mon 9/2910:10 pmHNL - MDW
2 stops14h 25mDelta
Deal found 8/17$505
This Southwest deal was found by Cheapflights users on 8/16. 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.
Sat 9/138:25 amMDW - HNL
1 stop17h 35mSouthwest
Fri 9/198:05 amHNL - MDW
1 stop11h 25mSouthwest
Deal found 8/16$511
This Southwest deal was found by Cheapflights users on 8/17. 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 10/77:40 amMDW - HNL
2 stops13h 45mSouthwest
Tue 10/149:00 pmHNL - MDW
1 stop12h 05mSouthwest
Deal found 8/17$516

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Honolulu 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 August 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Honolulu that are best for you.

Fly from

Midway

Fly to

Honolulu

Route

Depart

Return

Price

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 11/4

8:20 am-9:00 pm

1 stop16h 40m

Honolulu

Thu 12/4

9:25 pm-11:35 am

1 stop10h 10m

$465

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 10/29

9:35 am-7:09 pm

2 stops14h 34m

Honolulu

Mon 11/3

4:45 pm-8:40 am

1 stop11h 55m

$471

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/27

9:35 am-8:35 pm

2 stops16h 00m

Honolulu

Fri 10/31

4:50 pm-8:40 am

1 stop10h 50m

$471

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 10/25

9:20 am-8:26 pm

2 stops16h 06m

Honolulu

Fri 10/31

4:50 pm-8:40 am

1 stop10h 50m

$471

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/23

9:35 am-6:57 pm

2 stops14h 22m

Honolulu

Tue 10/7

1:20 pm-8:40 am

2 stops14h 20m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 11/11

9:30 am-9:45 pm

2 stops16h 15m

Honolulu

Tue 11/18

5:37 pm-12:32 pm

2 stops14h 55m

$476

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 9/14

8:20 am-9:00 pm

1 stop17h 40m

$233

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 10/21

6:25 am-1:25 pm

1 stop12h 00m

$233

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/20

11:00 am-9:00 pm

1 stop15h 00m

$233

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/13

8:25 am-9:00 pm

1 stop17h 35m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 15 results
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Best time to book a flight from Midway to Honolulu

Have a flexible travel schedule? Discover the best time to fly to Honolulu 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 Honolulu

What is the cheapest month to book a flight from Chicago Midway Airport to Honolulu?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $469). Flying from Chicago Midway Airport to Honolulu 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 Honolulu

Get insights into the airlines that provide service to Honolulu. 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 Honolulu. Reviews last updated August 18, 2025.
Read reviews from past customers who have flown Southwest and Delta from Chicago Midway Airport to Honolulu. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Honolulu. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Honolulu from Chicago Midway?

    Honolulu (HNL), located 4.4 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Honolulu. 2 airlines have flights to Honolulu from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Honolulu should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

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

    Departing from Chicago Midway Airport to Honolulu will take you 14h 34m. Chicago Midway Airport and Honolulu are separated by a distance of 4243 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago Midway Airport to Honolulu round-trip?

    Delta, at $427, was found to be the cheapest airline from Chicago Midway Airport to Honolulu. An alternate airline flying to your destination would be Southwest. Delta is currently priced 42% below the average price you’ll pay for this route.

  • Can I find deals for flights from Midway to Honolulu that include hotel bookings?

    Yes. In addition to deals on Midway to Honolulu flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Honolulu?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Honolulu.

  • Can I find deals for business class flights from Midway to Honolulu?

    Yes. Cheapflights offers flight deals from Midway to Honolulu 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 Honolulu?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $469). Flying from Chicago Midway Airport to Honolulu 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

Traveling to a place near Honolulu?

Book flights to Honolulu if you plan to visit one of these locations
Aiea
Kahuku

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Top 2 airlines flying from Midway to Honolulu

Discover the top 2 airlines that operate flights from Midway to Honolulu. 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$606FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$559Average$763FlexibilityNo cancel feeOn-time63%

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