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$240+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$471
(Delta)

One-way from

$240
(Delta)

Popular in

July

Cheapest in

January

Average price

$733
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. 13% potential increase in price ($114 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 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 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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 10/2911:55 amMDW - HNL
1 stop14h 05mSouthwest
Wed 11/59:55 pmHNL - MDW
1 stop14h 45mSouthwest
Deal found 9/14$479
This Delta deal was found by Cheapflights users on 9/14. 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 9/14$484
This Delta deal was found by Cheapflights users on 9/14. 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
Mon 11/311:32 pmHNL - MDW
2 stops14h 11mDelta
Deal found 9/14$490
This Delta deal was found by Cheapflights users on 9/12. 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 10/269:35 amMDW - HNL
2 stops14h 34mDelta
Fri 10/314:15 pmHNL - MDW
2 stops15h 16mDelta
Deal found 9/12$498
This Delta deal was found by Cheapflights users on 9/12. 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 10/276:00 amMDW - HNL
1 stop12h 32mDelta
Fri 10/314:50 pmHNL - MDW
1 stop10h 50mDelta
Deal found 9/12$510
This Southwest deal was found by Cheapflights users on 9/14. 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 10/279:25 pmMDW - HNL
1 stop17h 55mSouthwest
Thu 10/309:05 pmHNL - MDW
1 stop11h 55mSouthwest
Deal found 9/14$511
This Southwest deal was found by Cheapflights users on 9/12. 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 10/279:25 pmMDW - HNL
1 stop17h 55mSouthwest
Sat 11/17:50 pmHNL - MDW
1 stop12h 35mSouthwest
Deal found 9/12$512
This Delta deal was found by Cheapflights users on 9/12. 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 10/276:00 amMDW - HNL
1 stop12h 32mDelta
Sat 11/11:25 pmHNL - MDW
2 stops15h 30mDelta
Deal found 9/12$515
This Delta deal was found by Cheapflights users on 9/15. 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 10/219:20 amMDW - HNL
2 stops16h 06mDelta
Fri 10/314:50 pmHNL - MDW
1 stop10h 50mDelta
Deal found 9/15$516
This Delta deal was found by Cheapflights users on 9/15. 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 10/219:20 amMDW - HNL
2 stops16h 06mDelta
Sat 11/11:25 pmHNL - MDW
2 stops15h 30mDelta
Deal found 9/15$522
This Delta deal was found by Cheapflights users on 9/13. 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 12/59:34 amMDW - HNL
2 stops14h 54mDelta
Sun 12/145:37 pmHNL - MDW
2 stops14h 57mDelta
Deal found 9/13$524

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 September 15, 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

Wed 11/12

8:55 pm-1:45 pm

2 stops20h 50m

Honolulu

Wed 11/19

9:55 pm-5:15 pm

1 stop15h 20m

$512

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 12/5

9:34 am-8:28 pm

2 stops14h 54m

Honolulu

Fri 12/12

2:27 pm-9:19 am

2 stops14h 52m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 12/4

9:34 am-8:28 pm

2 stops14h 54m

Honolulu

Sun 12/14

5:37 pm-12:34 pm

2 stops14h 57m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 12/4

9:34 am-8:28 pm

2 stops14h 54m

Honolulu

Thu 12/11

2:27 pm-9:19 am

2 stops14h 52m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/27

9:35 am-8:26 pm

2 stops15h 51m

Honolulu

Mon 11/10

5:37 pm-12:34 pm

2 stops14h 57m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 10/21

9:20 am-8:26 pm

2 stops16h 06m

Honolulu

Sat 11/1

1:25 pm-9:55 am

2 stops15h 30m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 12/2

8:55 pm-11:20 am

1 stop18h 25m

Honolulu

Wed 12/10

9:25 pm-11:35 am

1 stop10h 10m

$525

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/27

9:25 pm-10:20 am

1 stop17h 55m

Honolulu

Mon 11/10

8:00 am-1:30 am

1 stop13h 30m

$534

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/27

9:25 pm-10:20 am

1 stop17h 55m

Honolulu

Mon 11/3

9:25 pm-3:00 pm

2 stops13h 35m

$539

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 11/12

9:32 am-8:15 pm

2 stops14h 43m

Honolulu

Mon 11/17

4:45 pm-8:52 am

1 stop12h 07m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 results
1
2

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 September 15, 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
4,242 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

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
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

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 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 54m. 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?

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$767FlexibilityNo cancel feeOn-time63%

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