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$244+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
1 adult, Economy
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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 November 14, 2025.

This Delta deal was found by Cheapflights users on 11/12. 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 12/76:00 amMDW - HNL
2 stops18h 29mDelta
Sun 12/1411:23 pmHNL - MDW
2 stops14h 55mDelta
Deal found 11/12$514
This Delta deal was found by Cheapflights users on 11/12. 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.
Fri 12/59:34 amMDW - HNL
2 stops14h 55mDelta
Wed 12/105:00 pmHNL - MDW
1 stop12h 54mDelta
Deal found 11/12$519
This Delta deal was found by Cheapflights users on 11/13. 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.
Wed 12/106:00 amMDW - HNL
1 stop13h 04mDelta
Tue 12/234:45 pmHNL - MDW
1 stop12h 04mDelta
Deal found 11/13$552
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:45 amMDW - HNL
1 stop12h 30mSouthwest
Thu 12/119:55 pmHNL - MDW
1 stop14h 45mSouthwest
Deal found 11/13$559
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:10 amMDW - HNL
1 stop11h 35mSouthwest
Tue 12/99:25 pmHNL - MDW
1 stop10h 10mSouthwest
Deal found 11/11$579
This Southwest deal was found by Cheapflights users on 11/12. 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.
Sun 12/79:45 pmMDW - HNL
1 stop17h 35mSouthwest
Tue 12/1612:35 pmHNL - MDW
2 stops12h 30mSouthwest
Deal found 11/12$584
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:20 amMDW - HNL
1 stop16h 40mSouthwest
Sun 12/149:00 pmHNL - MDW
1 stop14h 00mSouthwest
Deal found 11/11$587
This Delta deal was found by Cheapflights users on 11/12. 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.
Wed 12/106:00 amMDW - HNL
1 stop13h 04mDelta
Wed 12/172:26 pmHNL - MDW
2 stops14h 53mDelta
Deal found 11/12$588
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:20 amMDW - HNL
1 stop33h 07mMultiple Airlines
Wed 12/1011:30 pmHNL - MDW
2 stops31h 38mMultiple Airlines
Deal found 11/12$589

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 November 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$512
(Delta)

One-way from

$244
(Southwest)

Popular in

July

Cheapest in

January

Average price

$832
Provider with most accurate pricing for Chicago Midway-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Honolulu flights.
Search Deals
From Chicago Midway to Honolulu
Search Deals
One-way flight from Chicago Midway to Honolulu
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 14, 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

Mon 3/2

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Tue 3/3

11:37 pm-6:37 pm

2 stops15h 00m

$512

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/26

10:50 am-9:00 pm

1 stop14h 10m

Honolulu

Tue 3/3

9:55 pm-12:35 pm

1 stop10h 40m

$516

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 12/5

9:34 am-8:29 pm

2 stops14h 55m

Honolulu

Wed 12/10

5:00 pm-9:54 am

1 stop12h 54m

$519

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/15

8:05 am-9:00 pm

2 stops16h 55m

Honolulu

Mon 1/26

9:30 pm-2:45 pm

2 stops13h 15m

$527

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 1/21

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Tue 1/27

4:50 pm-10:01 am

1 stop13h 11m

$527

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 2/8

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Sun 3/8

4:20 pm-12:35 pm

2 stops15h 15m

$538

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 2/3

8:15 am-9:00 pm

1 stop16h 45m

Honolulu

Sun 2/8

9:55 pm-12:30 pm

1 stop10h 35m

$551

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 2/20

9:34 am-9:56 pm

2 stops16h 22m

Honolulu

Mon 3/2

5:15 pm-12:48 pm

2 stops15h 33m

$553

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/9

10:05 am-9:00 pm

1 stop15h 55m

Honolulu

Sun 3/15

8:10 am-4:35 am

1 stop15h 25m

$554

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 2/27

9:34 am-9:56 pm

2 stops16h 22m

Honolulu

Sun 3/8

3:45 pm-8:50 am

1 stop12h 05m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 23 results
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Compare providers for flights from Midway to Honolulu

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Honolulu in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Honolulu flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Honolulu flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Honolulu flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Honolulu flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Honolulu flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $324). Flying from Chicago Midway Airport to Honolulu in July is currently the most expensive (average of $886). 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 November 14, 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

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8,009 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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 13h 11m. 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 $442, 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 40% 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $324). Flying from Chicago Midway Airport to Honolulu in July is currently the most expensive (average of $886). 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
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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 November 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$442Average$613FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$767FlexibilityNo cancel feeOn-time63%

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